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Location: Madrid Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU'LL DO - GTM technical expert: Design and demo Sierra’s incredible Agent product, offering technical solutions to solve for our customer’s needs, and answering technical questions about our solutions. - Cross-functional work: You will work directly with our Sales, Product and Agent Engineering teams to both drive our GTM function, as well as continuously improve our Agents through our customer-driven product development philosophy. - Lead & support our customers: As a GTM and technical leader in the earliest conversations with our future customers, you will both understand and anticipate their needs to continue our industry-leading AI solution. WHAT YOU'LL BRING - 5-7+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales. - Exceptional verbal and written communication abilities. Professional fluency in both Spanish and English. - Past experience in demo building, and presenting, and working with customers or clients in the GTM function. - Experience in relationship-building with potential customers, including executives and technical leaders. - Experience in leading the sales process with Enterprise customers. - Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience - Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience. EVEN BETTER... - AI-related experience (or experience in a similarly modern and highly technical industry). - Experience translating code, technical logic and user requirements to product and engineering requirements. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: San Francisco, CA Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU'LL DO We're looking for a business value strategist to join our pricing team. You'll partner with sales and customers throughout complex enterprise sales cycles to develop customer-specific value frameworks, build rigorous ROI models and investment cases grounded in operating and financial metrics, and translate Sierra's impact into measurable outcomes such as lower operating costs, incremental revenue, and stronger customer loyalty. You'll also create and scale repeatable, industry-specific business cases and establish Sierra's business value framework from the ground up. This is a hands-on role for someone who can bring structure to ambiguous problems, develop rigorous analysis, and has strong communciation. - Support complex enterprise sales cycles by developing ROI models, evaluating tradeoffs, and presenting recommendations to senior decision-makers - Shape commercial strategy by connecting the value Sierra delivers to our outcomes-based pricing model - Develop industry-specific benchmarks, frameworks, and tools that make Sierra’s business value clear and repeatable WHAT YOU'LL BRING - 5+ years of experience in value engineering, monetization strategy, consulting, strategic finance, or a similar role focused on quantifying and communicating business impact - Advanced financial modeling and analytical skills, with a track record of building rigorous ROI models and investment cases - Experience supporting complex enterprise sales cycles and engaging senior decision-makers - Ability to partner effectively with sales teams and customer stakeholders across finance, operations, and executive leadership - Degree in Business Administration, Finance, Economics, or a related field, or equivalent professional experience EVEN BETTER... - Experience building and scaling a business value methodology, program, or center of excellence from the ground up - Familiarity with AI, conversational AI, or customer service operations - Previous experience in a zero-to-one startup or fast-paced, high-growth environment OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: San Francisco, CA; New York, NY Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU’LL DO As an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai on a Flagship Deployment, you’ll lead the end-to-end deployment for one of Sierra’s largest and most strategic customers. You own how Sierra's AI agents come to life, often managing scaled deployments as well as new proofs of concept within the same account. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer's thorniest, highest-stakes problems into agents that measurably move their business. - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it's the best version of itself in the real world. You'll have real ownership and autonomy over the outcome. - Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and shape the AI strategy that gets them there. - Partner with the customer's working teams and executives day to day. Oversee overall program management while ensuring ongoing executive alignment on the long term roadmap. - Navigate enterprise complexity with cross-functional teams (engineering and product). At this scale, every big technical discussion is also a negotiation — you'll need to read the implications in real time, hold your ground, and steer toward the right outcome. Expect to work across business units, procurement, compliance, and senior execs. - Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next. - Manage internal resourcing requirements. Ensure that your deployment is appropriately resourced today and into the future - Drive financial success for both the customer and Sierra. Ensure value exchange is optimized, drive revenue upside for Sierra, and work internally to manage down cost to serve over time, improving margins. - Partner with Sales on commercial strategy. You are a key player in closing new business within the deployment by identifying opportunities, aligning resources, and EXAMPLE PROJECTS These are the kinds of projects that strategists on our team have worked on recently: - Plan, organize, and execute on-site business reviews onsite at a Fortune 100 company with Sierra cofounders in attendance - Manage a portfolio of agents across a customer deployment as they scale nationally, to new use cases, and grow in technical complexity - Build relationships throughout the customer’s organization, unlocking high trust, social capital, and ultimately new ARR - Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation. - Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner. - Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome https://sierra.ai/blog/outcome-based-pricing-for-ai-agents week over week. WHAT YOU’LL BRING - Proven track record: 10+ years of relevant experience driving results in high stakes situations in an enterprise customer facing role, ideally in a dedicated, embedded model with a named enterprise account — you know what it means to be accountable for a relationship at that depth. - Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships. - Communication. Clear, direct, and persuasive across technical and non-technical audiences. - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast. - Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion. - Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes. EVEN BETTER... - You've run a company, business unit, forward deployed team, or have comparable experience in general management of business initiatives that require technical aptitude, strategic leadership, operational excellence, and financial outcome accountability. - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts. - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: New York, NY; San Francisco, CA Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. Help build the operational foundation that powers Sierra's ecosystem—and the global community building the future of AI agents. Sierra's ecosystem is growing rapidly. Customers, partners, and developers around the world are building on Sierra to create the next generation of AI-powered experiences. As that community grows, we're looking for an Ecosystem Operations Manager to help scale the programs, systems, and operations that enable it to thrive. This is a high-impact, cross-functional role within Sierra's Partnerships & Ecosystems team. You'll help operate and improve Sierra University, partner enablement, developer relations, and builder community programs while strengthening the operational foundation that enables the ecosystem to scale. Working closely with Product, Engineering, Marketing, GTM, Agent Development, and Partnerships, you'll improve processes, coordinate programs, and build the operational rigor that allows our ecosystem to grow efficiently. We're looking for someone who enjoys bringing order to complexity—someone who can build scalable processes, execute high-impact programs, and continuously improve how we serve customers, partners, and builders. WHAT YOU'LL DO - Scale Sierra University by managing curriculum operations, certification programs, learner journeys, platform administration, and governance. - Coordinate programs that grow Sierra's global builder community, creating opportunities for customers and partners to learn, connect, and succeed. - Drive partner enablement operations in partnership with the Partnerships team, ensuring partners have the training, resources, and operational support they need to activate quickly. - Create and maintain developer-facing resources—including documentation, tutorials, videos, and technical enablement materials—that help builders get the most from Sierra's platform. - Plan and execute ecosystem events, including certification launches, builder summits, partner workshops, developer days, and community activations. - Build and improve the operational systems, reporting, and processes that enable the Partnerships & Ecosystems team to scale efficiently. - Partner across Product, Engineering, Marketing, GTM, Agent Development, and Partnerships to coordinate ecosystem initiatives and keep programs moving. - Measure ecosystem health through certification adoption, partner activation, community engagement, content effectiveness, and customer feedback, and use those insights to continuously improve how Sierra serves builders and partners. WHAT YOU'LL BRING - 6–8+ years of experience in ecosystem operations, developer relations, community programs, partner enablement, program management, or a related function at an enterprise SaaS or developer platform company. - Experience operating and scaling customer, partner, or developer programs. - Experience creating developer-facing content, including documentation, tutorials, videos, or technical enablement materials. - Fluent in modern AI tools and workflows, with hands-on experience leveraging AI to improve productivity and a strong understanding of how AI agents, LLMs, and developer tools are transforming the way software is built, shipped, and adopted. - Excellent written and verbal communication skills, with experience producing both customer-facing content and executive-ready communications. - Highly organized, execution-oriented, and energized by building scalable programs in fast-moving environments. - Willingness to travel as needed to support Sierra University, partner enablement, ecosystem events, builder programs, and community engagement. EVEN BETTER... - Experience at companies with scaled developer ecosystems, learning platforms, or partner communities. - Experience supporting both customer and partner audiences. - Familiarity with learning management systems, community platforms, event operations, and modern content creation tools. - Experience working with AI platforms, developer tools, or enterprise software ecosystems. - Prior software development, solutions engineering, or technical implementation experience. - Experience scaling global ecosystem programs in fast-growing environments with limited existing processes or playbooks. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: San Francisco, CA; New York, NY Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU’LL DO As an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai, you own how Sierra’s AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer’s thorniest, highest-stakes problems into agents that measurably move their business. - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it’s the best version of itself in the real world. You’ll have real ownership and autonomy over the outcome. - Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers’ executives, understand what success actually means to their business, and shape the AI strategy that gets them there. - Partner with the customer’s working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch. - Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next. EXAMPLE PROJECTS These are the kinds of projects that strategists on our team have worked on recently: - Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers. - Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation. - Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services for examples. - Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner. - Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome https://sierra.ai/blog/outcome-based-pricing-for-ai-agents week over week. WHAT YOU’LL BRING - Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships. - Communication. Clear, direct, and persuasive across technical and non-technical audiences. - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast. - Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion. - Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes. - Genuine interest in Financial Services and improving the end customer experience. Experience in financial technology, implementations at financial institutions, working inside of these institutions or familiarity with financial services security and compliance requirements (fair lending, PII handling, etc.) are a strong plus. EVEN BETTER... - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts. - You’ve been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed. - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: San Francisco, CA Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU’LL DO - Own frontend across product and marketing surfaces: You will work across both our core product interface and customer-facing web pages, ensuring a cohesive, polished user experience across all touch points. This includes building features in the web app and also collaborating on our website to keep branding and user experience consistent and high-quality. - Build content infrastructure that unblocks the team: You'll develop our CMS (we use Sanity) to give content and marketing teams self-serve tooling, structured content models, and preview/staging workflows, so routine changes don't depend on engineering. You'll design content schemas and editing experiences that let non-engineers move quickly and confidently. - Champion growth: You'll partner with marketing, sales, and operations to implement analytics and enable experimentation, turning business goals into shipped, instrumented features so we always know what's actually working. - Make localization first-class: You'll support localization and internationalization — multilingual content, translation workflows, and the infrastructure behind them, so non-English experiences are genuinely first-class rather than afterthoughts. - Treat performance as a feature: You'll own Core Web Vitals, media and asset optimization, and the diagnosis of the subtle issues: layout shift, lazy-loading, video quality, render timing. You care about speed, and you measure it. - Hold a high bar for accessibility: You'll champion semantic markup, keyboard navigation, screen-reader support, and WCAG-minded component design, ensuring the site is usable by everyone who visits it. WHAT YOU'LL BRING - Marketing and growth fluency: You've worked on marketing or growth-facing web before, and you understand the business context — funnels, conversion, SEO, analytics, and A/B testing—not just the code. We care about this more than years of experience or exact seniority. - Strong frontend fundamentals: You're fluent in modern JavaScript and TypeScript and React (or a similar framework), with a real sense for UI/UX craft and an instinct for getting the small details right. - A genuine commitment to performance and accessibility: You care about both deeply and can point to specific, concrete things you've done to improve them in production. - Comfort with structured content: You've worked with a headless CMS and structured content models before. Sanity experience is a plus. - Strong cross-functional collaboration: You work well with non-engineers — designers, content writers, and marketers — and can translate their goals into technical work, and technical tradeoffs back into terms they can act on. Even better... - Localization and i18n experience: You've worked with internationalization systems and translation tooling before. - Analytics and experimentation depth: You're familiar with web analytics and experimentation platforms and know how to use them to drive decisions. - Third-party integration experience: You've integrated services like video hosting or error monitoring into a content workflow. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: London Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU’LL DO We're looking for a pricing strategist to join our GTM operations team. You'll work with our sales team to develop and deliver pricing proposals and ROI case studies for customers, and to help them execute deals. You'll also collaborate with product, marketing, and operations teams to define our overall pricing and packaging strategy. WHAT YOU’LL BRING - 4+ years of experience in consulting, banking, strategy, or business operations. Startup experience in a similar GTM operations role, specifically SaaS pricing, sales, marketing, and operations strongly preferred. - Experience negotiating complex customer partnerships - Familiarity with navigating sales cycles - Strong understanding of developing GTM operations using data-driven decision-making - Degree in Business Administration, Finance, or related field, or equivalent professional experience EVEN BETTER… - Experience in partnerships, business development, and value engineering roles - Familiarity with AI or conversational AI technologies - Previous 0-1 startup or fast-paced high-growth environment experience OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: San Francisco, CA; New York, NY Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. ABOUT THE HEALTHCARE TEAM - Our healthcare agents already reach over 50% of U.S. families. We partner with leading health plans, providers, and healthcare platforms to deliver AI agents that handle some of the most sensitive and high stakes conversations in any industry. From helping members understand their benefits to resolving billing questions with empathy, our healthcare agents are transforming how patients and policyholders interact with the healthcare system. - Our healthcare customers include major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms. - Join us to transform the patient experience across the healthcare system—and help build technology that makes care more accessible, more human and more affordable for everyone. WHAT YOU'LL DO - Design integrations grounded in real healthcare workflows. Translate customer requirements into clear recommendations on interfaces, data flows, and EHR configuration. Identify assumptions, tradeoffs, and limitations so engineering teams have an actionable implementation plan. - Resolve customer-specific EHR complexity. Understand how each organization configures and operates its EHR, including scheduling rules, patient identity, permissions, and workflow dependencies. Work with customer analysts, vendor teams, and Sierra engineers to investigate unexpected behavior and resolve integration blockers. - Guide integration readiness through go-live. Define customer setup requirements, dependencies, and validation criteria. Guide EHR and IT teams through application registration, access provisioning, environment setup, and workflow testing, partnering with engineers to verify that integrations behave as intended. - Bring EHR expertise to customer discovery. Partner with Sales, Sales Engineering, and Agent Development to assess feasibility, explain integration requirements, and scope achievable projects. Make clear what Sierra supports today and what requires additional configuration or development. - Shape Sierra’s healthcare integration roadmap. Evaluate vendor capabilities, integration programs, and emerging customer needs. Recommend where to invest, distinguishing reusable platform capabilities from customer-specific configuration and implementation work. - Make each implementation easier than the last. Turn deployment experience into reference designs, implementation guides, and internal training. Help teams apply proven approaches and recognize when a customer’s requirements call for a different design. WHAT YOU'LL BRING - 5+ years of experience in healthcare interoperability or EHR implementation, with direct responsibility for designing or delivering integrations at an EHR vendor, health system, healthcare technology company, or implementation consultancy. - Deep expertise in at least one major EHR ecosystem, such as Epic, athenahealth, Oracle Health, eClinicalWorks, MEDITECH, or similar systems. You understand its integration options, configuration model, and implementation processes, and can investigate unfamiliar capabilities independently. - Practical knowledge of patient-access workflows, such as scheduling, registration, or referral management. You can explain how operational rules and customer configuration affect what an integration can do. - Technical fluency in healthcare integrations. You can read API documentation, interpret requests and responses, and troubleshoot data and configuration issues. You have hands-on experience with relevant approaches such as FHIR, HL7v2, vendor APIs, or file-based exchange, and can explain when to use them. - A track record of taking third-party integrations through deployment. You have worked through application registration, authentication and permissions, test and production environments, workflow validation, and go-live dependencies. - Clear communication and independent judgment. You can lead discovery with EHR analysts and operational teams, turn incomplete information into an implementation plan, and explain recommendations to software engineers and business stakeholders. You know when to validate an assumption before committing to an approach. EVEN BETTER... - Epic certifications in areas such as Bridges, Cadence, Prelude, or Interconnect, or comparable expertise in another EHR ecosystem. - Experience across multiple EHR vendors or health systems, particularly integrating third-party products into patient-access or contact-center workflows. - Experience using SQL, scripts, or code to investigate integration issues, or working with teams building AI agents for healthcare. - Hands-on software development experience, including building or extending integrations with EHRs or other healthcare systems. - Comfortable contributing directly to integration code, including implementing API calls, troubleshooting failures, and writing tests. Experience with TypeScript, Go, or Python is a plus. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: San Francisco, CA Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU'LL DO: - Drive partner activation through onboarding, enablement, certification, governance, and operational support programs that help product, strategic, and channel partners become productive quickly. - Build and continuously improve the systems, playbooks, processes, and partner-facing resources that enable Sierra’s partnership ecosystem to scale, including onboarding guides, enablement content, FAQs, and operational documentation. - Coordinate cross-functional execution across Product, Engineering, Sales, Solutions Engineering, Customer Success, Marketing, Legal, GTM Operations, and Partnerships to support product launches, technology integrations, joint GTM programs, co-sell motions, and strategic initiatives. - Plan and execute ongoing partner engagement and governance, including enablement sessions, webinars, QBRs, executive business reviews, newsletters, office hours, partner events, and ongoing partnership management. - Build reporting and use data to improve partnership health, tracking partner activation, engagement, pipeline contribution, partner-influenced revenue, and overall performance while identifying friction and continuously improving how Sierra launches, activates, and scales partnerships. WHAT YOU'LL BRING: - 6+ years of experience in partnership management, partner programs, partner success, ecosystem operations, program management, or a related function within an enterprise SaaS company. - Experience launching, activating, and scaling strategic partnerships, including partner onboarding, enablement, certification, joint GTM execution, technology launches, and ongoing partner success. - Strong cross-functional operator with experience influencing Product, Engineering, GTM, Customer Success, Marketing, Legal, and external partners without direct authority, and exceptional organizational, communication, analytical, and project management skills. - Comfortable with APIs, integrations, and technical product concepts, with the ability to collaborate closely with technical teams without needing to be an engineer. - Fluent with modern AI tools and workflows, actively using AI to improve your work and understanding how AI is changing enterprise software, customer engagement, and partnership models; thrives in ambiguity and enjoys turning strategy into repeatable execution. EVEN BETTER... - Experience supporting and scaling strategic partnership programs across product and technology partnerships, cloud ecosystems, systems integrators, strategic alliances, or channel networks, ideally in a high-growth global environment. - Experience working across enterprise software ecosystems and partners such as AWS, Google Cloud, Microsoft, Salesforce, ServiceNow, Stripe, Twilio, Snowflake, Databricks, or large global systems integrators, with familiarity across PRM, CRM, partner enablement, learning management, and collaboration platforms. - Technical and AI ecosystem experience, including AI platforms, developer tools, or enterprise software, with prior software development, solutions engineering, or technical implementation experience a plus. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: San Francisco, CA; Washington, D.C. Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU'LL DO - Own the end-to-end partnership strategy for Sierra’s US, Canada, and UK Government & SLED ecosystem, identifying, prioritizing, recruiting, and structuring the systems integrator, reseller, distributor, and strategic alliances that will most accelerate Sierra’s growth and expand our public-sector reach. - Build and lead joint go-to-market strategies with key partners, developing compelling joint value propositions, identifying priority accounts and use cases, and aligning sales motions, pipeline goals, and shared success metrics to drive measurable commercial outcomes. - Build a scalable partner program and enablement engine from the ground up, including training, certification paths, sales plays, field-facing materials, commercial frameworks, and onboarding programs that give partners the tools and confidence to effectively position, sell, and deliver Sierra. - Own and grow strategic partner relationships from initial engagement through long-term success, cultivating executive-level sponsorship while establishing the operating rhythms, joint planning, business reviews, governance, and scorecards needed to keep partnerships accountable, productive, and scaling over time. - Serve as the connective tissue between Sierra and the broader public-sector partner ecosystem, partnering closely with Sales, Marketing, Product, and Legal; bringing market intelligence and partner feedback back into Sierra; representing the company at key industry and procurement events; and using pipeline and performance data to determine where to invest, course-correct, or evolve our partnership strategy. WHAT YOU'LL BRING - 10+ years of experience in strategic partnerships, alliances, or channel strategy, with significant experience across US, Canada, and/or UK Government and SLED markets and a proven track record of building and scaling partner programs that drive engagement and pipeline. - Strong relationships across the government technology ecosystem, including resellers, systems integrators, distributors, and strategic partners such as Carahsoft, Deloitte, Accenture Federal Services, or comparable public-sector organizations. - Deep understanding of government procurement and public-sector requirements, including RFPs/RFIs, cooperative purchasing vehicles, GSA schedules, CCS/G-Cloud frameworks, Canadian procurement vehicles, and relevant compliance, security, and accessibility requirements. - Strong executive presence and relationship-building skills, with a demonstrated ability to earn senior-level trust and sponsorship while developing GTM frameworks, enablement programs, and operating cadences that scale partnerships. - AI fluency and a builder mindset, with experience leveraging AI-powered tools and insights in day-to-day work and applying that knowledge to partnerships around an AI-native product like Sierra, along with the ability to travel across the US, Canada, and UK as needed. EVEN BETTER... - Experience working at or partnering closely with government-focused organizations such as Carahsoft, Deloitte, or Accenture Federal, ideally within a high-growth enterprise company where you helped build and scale a public-sector partner ecosystem. - Experience structuring and growing strategic partnerships, including negotiating commercial terms, developing co-sell and governance frameworks, and driving joint GTM initiatives, customer events, executive engagement, and partner marketing programs. - Knowledge of the government technology landscape, ideally including CX/customer service technology, AI/ML applications and public-sector AI policy/procurement trends, with an existing security clearance or eligibility to obtain one where applicable. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: San Francisco, CA; New York, NY Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU’LL DO As an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai, you own how Sierra’s AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer’s thorniest, highest-stakes problems into agents that measurably move their business. - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it’s the best version of itself in the real world. You’ll have real ownership and autonomy over the outcome. - Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers’ executives, understand what success actually means to their business, and shape the AI strategy that gets them there. - Partner with the customer’s working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch. - Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next. EXAMPLE PROJECTS These are the kinds of projects that strategists on our team have worked on recently: - Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers. - Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation. - Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services for examples. - Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner. - Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome https://sierra.ai/blog/outcome-based-pricing-for-ai-agents week over week. WHAT YOU’LL BRING - Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships. - Communication. Clear, direct, and persuasive across technical and non-technical audiences. - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast. - Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion. - Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes. EVEN BETTER... - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts. - You’ve been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed. - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: Singapore Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU’LL DO - Design and deliver production-grade AI agents https://sierra.ai/blog/meet-the-ai-agent-engineer: You'll build and ship highly performant, reliable, and intuitive AI agents that are central, mission-critical and drive revenue directly to Sierra's growth. These aren't prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce. - Drive the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle (ADLC): You'll have complete ownership and autonomy from initial pilot through deployment and continuous iteration. You'll be responsible for building, tuning, and evolving AI agents in production environments, defining the standard for ADLC best practices along the way. - Partner with large enterprises and cutting-edge startups: You’ll work directly with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and build AI agents that transform how they operate at scale. You'll also partner with the most cutting-edge startups in Silicon Valley, embedding AI agents across their entire business stack to drive innovation and efficiency. - Build the future of the platform: Your direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development and Sierra's product. EXAMPLE PROJECTS These are some examples of projects that engineers on our team have worked on recently: - Design and build AI agents for large telecommunications and media companies that consistently outperform human agents in managing subscription churn - Develop and refine AI agents capable of navigating complex customer interactions, like troubleshooting a broken device and personalizing product recommendations - Create generalizable AI agent frameworks tailored for industry-specific use cases. See some examples in our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services! - Facilitate design partnerships for new product initiatives, such as new agent architectures, self-service capabilities, and generative agent development - Experiment with the latest voice models and figure out how to integrate them at scale to enterprise-grade customers WHAT YOU'LL BRING - Experience building and scaling end-to-end production systems - Strong technical problem-solving skills, especially in fast-changing, ambiguous environments - A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship - Comfort working directly with customers to understand their needs and solve real-world problems - Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences EVEN BETTER... - Experience building or deploying AI/LLM systems in production - Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed - Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering - Prior experience with React, TypeScript, and/or Go - Previous roles where you interfaced with customers or led technical projects with external stakeholders OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: Singapore Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. As a Software Engineer Intern, Agent, you'll work directly on production AI agents for Sierra's customers. You'll gain hands-on experience contributing to the design and development of AI agents, shipping features, and learning from real-world use cases at scale. If you're hungry to shape and learn from the most important technological wave in history, come build at Sierra.   WHAT YOU'LL BRING - Pursuing a bachelor's or master's degree in computer science or a related field - Strong technical problem-solving skills, especially in fast-changing, ambiguous environments - A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship - Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences EVEN BETTER - Experience building or deploying AI/LLM systems in production - Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering - Prior experience with React, TypeScript, and/or Go INTERN QUALIFICATIONS - The intern program is open to students graduating December 2027 - June 2028 - Note: The full benefits listed below are available only to full-time employees. Interns are eligible for a monthly stipend for health insurance, daily lunch, and, of course, free alphorn lessons. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: London Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU'LL DO As an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai, you own how Sierra's AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer's thorniest, highest-stakes problems into agents that measurably move their business. - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it's the best version of itself in the real world. You'll have real ownership and autonomy over the outcome. - Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and shape the AI strategy that gets them there. - Partner with the customer's working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch. - Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next. EXAMPLE PROJECTS These are the kinds of projects that strategists on our team have worked on recently: - Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers. - Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation. - Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services for examples. - Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner. - Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome https://sierra.ai/blog/outcome-based-pricing-for-ai-agents week over week. WHAT YOU'LL BRING - Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships. - Communication. Clear, direct, and persuasive across technical and non-technical audiences. - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast. - Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion. - Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes. EVEN BETTER... - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts. - You've been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed. - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: London Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU'LL DO As an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai, you own how Sierra's AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer's thorniest, highest-stakes problems into agents that measurably move their business. - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it's the best version of itself in the real world. You'll have real ownership and autonomy over the outcome. - Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and shape the AI strategy that gets them there. - Partner with the customer's working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch. - Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next. EXAMPLE PROJECTS These are the kinds of projects that strategists on our team have worked on recently: - Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers. - Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation. - Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services for examples. - Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner. - Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome https://sierra.ai/blog/outcome-based-pricing-for-ai-agents week over week. WHAT YOU'LL BRING - Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships. - Communication. Clear, direct, and persuasive across technical and non-technical audiences. - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast. - Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion. - Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes. EVEN BETTER... - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts. - You've been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed. - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: London Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU'LL DO As an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai, you own how Sierra's AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer's thorniest, highest-stakes problems into agents that measurably move their business. - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it's the best version of itself in the real world. You'll have real ownership and autonomy over the outcome. - Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and shape the AI strategy that gets them there. - Partner with the customer's working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch. - Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next. EXAMPLE PROJECTS These are the kinds of projects that strategists on our team have worked on recently: - Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers. - Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation. - Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services for examples. - Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner. - Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome https://sierra.ai/blog/outcome-based-pricing-for-ai-agents week over week. WHAT YOU'LL BRING - Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships. - Communication. Clear, direct, and persuasive across technical and non-technical audiences. - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast. - Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion. - Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes. EVEN BETTER... - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts. - You've been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed. - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: San Francisco, CA Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU'LL DO - As an Executive Assistant supporting the Office of the Co-Founders at Sierra, you will provide a wide range of strategic and administrative support to our Co-Founders and their teams. - Play a pivotal, high-trust role in a dynamic, fast-paced environment. You’ll partner closely with the existing executive support team to execute complex logistics, travel, meetings, events, and special projects with precision and foresight. - Act as a second assistant to our Co-Founders, coordinating complex travel, running logistics for all onsite meetings, helping the team with projects (large trip planning, events, etc) and generally be ready and able to jump in when extra support is needed. - Anticipate needs, identify potential issues, and proactively develop solutions that keep priorities and commitments moving forward. - Serve as a trusted liaison to internal teams, vendors, and external partners, building strong relationships while safeguarding the priorities of the Office of the Co-Founders. - Plan and execute leadership travel, team off-sites, executive dinners, on-site meetings, and other internal or personal events as needed. - Take ownership of evolving requests and projects, remaining flexible and ready to provide additional support wherever it is most needed. - Handle sensitive information and materials with the utmost confidentiality, discretion, and sound judgment. WHAT YOU'LL BRING - 3+ years of experience in executive support or a similar high-level administrative role. - Willingness and ability to work on-site in San Francisco up to five days per week, including consistent presence when the co-founders are on-site. - Exceptional attention to detail and an anticipatory, white-glove service mindset, with the ability to operate independently and deliver polished, seamless support with limited direction. - Exceptional organizational and time-management skills, with the ability to manage competing priorities accurately in a fast-paced environment. - Proven ability to partner effectively with senior executives, cross-functional teams, vendors, and external stakeholders. - Advanced proficiency with Google Workspace and Slack, along with the ability to learn new tools quickly. EVEN BETTER... - Experience in a fast-growing, in-person start-up environment. - Experience working with C-suite executives. - Experience working within a dual, floating, or team-based Executive Assistant structure. - Experience managing complex travel, executive events, and high-touch on-site logistics. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: San Francisco, CA; New York, NY; Atlanta, GA; Washington, D.C. Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. ABOUT THE PUBLIC SECTOR TEAM - Sierra recently received FedRAMP High https://sierra.ai/blog/certified-fedramp-high certification, enabling us to bring our industry-leading technology to partners in the US public sector. We’re now building our founding public sector team to redefine the relationship between the government and its citizenry. - Today, our agents already enable citizens to access social services, report fraud, and understand complex government systems. Simultaneously, they empower government officials to better hear the concerns and inquiries of their constituencies. - We are explicitly nonpartisan and committed to empowering public servants to leverage AI to advance their important missions. - In our journey, we are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and Family. These values are the foundation of our work, and we are committed to upholding them in everything we do. WHAT YOU'LL DO - Build Sierra’s public sector business: Own a portfolio of strategic Federal, state or local government accounts, develop territory and account plans, build qualified pipeline, and consistently achieve or exceed revenue targets. - Create opportunities around mission outcomes: Develop trusted relationships with agency leaders, program executives, technology teams, procurement officials, and other stakeholders. Translate priorities such as constituent access, service delivery, workforce effectiveness, and program integrity into compelling AI agent opportunities. - Lead complex sales cycles from discovery through award: Orchestrate executive alignment, solution development, business cases, security and legal reviews, pricing, proposal strategy, negotiation, and close across long, multi-stakeholder government buying processes. - Design the path to contract: Understand how each customer can buy and shape a practical acquisition strategy early. Navigate direct awards, competitive solicitations, pilots, task orders, and contract vehicles—including GSA schedules, GWACs, IDIQs, BPAs, state schedules, and cooperative purchasing agreements—as relevant to the opportunity. - Build and execute capture plans: Qualify opportunities with discipline; map decision-makers, influencers, incumbents, competitors, funding sources, fiscal-year timing, acquisition milestones, and win themes; and lead the internal cadence required to move from early demand to award. - Develop Sierra’s partner ecosystem: Build productive relationships with prime contractors, systems integrators, resellers, distributors, small-business partners, and other technology providers. Know when Sierra should sell directly, participate as a subcontractor, establish a teaming arrangement, or pursue a partner-led transaction—and align incentives and responsibilities accordingly. - Shape prime and teaming relationships: Identify where Sierra can strengthen a prime contractor’s solution and where partners can provide customer access, past performance, implementation capacity, or a procurement pathway. Negotiate clear account alignment, deal registration, workshare, and go-to-market plans that create durable value for the customer and Sierra. - Run high-quality bids and proposals: Partner with public sector leadership, legal, security, product, engineering, and delivery teams on RFIs, RFPs, sources sought, oral presentations, and other procurement responses. Make thoughtful bid/no-bid recommendations and ensure every submission is compliant, differentiated, and precise. - Operate as part of the customer’s team: Earn trust across senior agency leadership and working teams by understanding the mission, communicating candidly, and remaining accountable from the first meeting through deployment and expansion. - Help build the public sector go-to-market motion: As an early member of the team, improve our account segmentation, capture process, partner strategy, contract-vehicle roadmap, forecasting, and repeatable sales playbooks. Bring market signals back to product and company leadership to help shape Sierra’s platform and public sector strategy. - Operate as an AI-native seller: Use AI throughout the sales cycle—from account research and personalized outreach to call synthesis, opportunity planning, proposal development, and forecasting—so you can spend more time on judgment, strategy, and customer relationships. WHAT YOU'LL BRING - Meaningful enterprise technology sales or business development experience, including significant experience selling software, cloud, data, or AI solutions to U.S. government customers. - A demonstrated record of building pipeline, exceeding quota, and closing complex six- and seven-figure opportunities with long sales cycles and multiple technical, mission, executive, and procurement stakeholders. - Strong fluency in government acquisition and procurement, including funding and budget cycles, competitive solicitations, proposal processes, task orders, and common Federal or state contract vehicles. - Experience developing and executing capture strategies before a solicitation is released—not simply responding once an RFP is public. - A strong network and demonstrated ability to work with government technology partners, including prime contractors, systems integrators, resellers, distributors, and small-business teaming partners. - Sound judgment about direct, channel, prime/subcontractor, and teaming models, with the ability to select and execute the right path for a particular agency and opportunity. - The ability to build credibility with agency executives, program leaders, contracting and procurement officials, security teams, and technical stakeholders—and to align those groups around a shared path forward. - Excellent executive communication, negotiation, account planning, and forecasting skills. You are rigorous about details, procurement milestones, and next steps. - A passion for public sector work and a belief in the potential of government institutions to improve outcomes for the people they serve. - Comfort operating with high ownership in an early-stage business: you create structure where it does not yet exist, move with urgency, and collaborate deeply across functions. EVEN BETTER... - Experience helping launch or scale a public sector business for a high-growth software company. - Established relationships across Federal civilian agencies, state governments, or the government contractor and systems integrator ecosystem. - Familiarity with the FAR and related acquisition frameworks, government cloud and security requirements, and the commercial implications of FedRAMP High. - Experience shaping and closing outcome-based, usage-based, or other nontraditional software agreements in the public sector. - Experience with AI, conversational systems, customer experience technology, contact centers, or digital government services—and the ability to speak credibly with both mission and technical leaders. - Experience operating alongside founders or senior executives in high-stakes customer and partner engagements. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.