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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. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. WHAT YOU’LL DO As a Forward Deployed Infrastructure Engineer at Sierra, and a founding member of this function, you will own the end-to-end lifecycle of customer deployments, while helping define how Sierra’s AI platform is deployed and operated across enterprise environments. You'll work directly with enterprise customers to architect, deploy, upgrade, and manage Sierra's AI platform infrastructure — ensuring every deployment meets their security, compliance, and operational requirements. In addition, you’ll establish the standards, tooling, and processes that make deployments scalable and repeatable, and partner cross-functionally with Engineering, Product, Sales, and Customer Success. This role will define how Sierra scales some of its most complex customer engagements. - Own deployment architecture conversations and execution — designing and implementing deployment strategies across customer environments, including VPC configuration, permissioning, networking, and infrastructure provisioning. - Manage the full infrastructure lifecycle for some of Sierra’s most critical customers: initial deployment, ongoing upgrades, scaling, and incident support. - Develop and maintain deployment runbooks, upgrade procedures, and automation tooling to make operations repeatable and reliable. - Partner with engineering teams to ensure Sierra's platform is deployable and operable across diverse customer requirements. - Work with customers' platform engineering, security, and DevOps teams to navigate their infrastructure constraints and compliance requirements. - Collaborate with Sales and Customer Success to scope infrastructure requirements during pre-sales and onboarding, translating customer needs into concrete deployment plans. WHAT YOU'LL BRING - 4+ years of experience in infrastructure, DevOps, platform engineering, or solutions architecture roles — with significant time spent on customer-facing deployment work. - Deep experience with AWS services, Terraform, container orchestration, and cloud networking (VPCs, IAM, DNS, load balancing). - Track record of managing deployments in customer-owned cloud environments, including navigating security reviews, compliance requirements, and change management processes. - Ability to navigate ambiguity with enterprise stakeholders — from platform engineers to CISOs — and turn infrastructure conversations into actionable deployment plans. - Strong operational instincts: you think about upgrades, rollbacks, monitoring, and failure modes from the start, not as an afterthought. - Comfortable working in a fast-moving environment and collaborating across engineering, product, and go-to-market teams. - Degree in Computer Science or a related field, or equivalent professional experience. EVEN BETTER… - Hands-on experience with Go services, GraphQL APIs, or LLM infrastructure in production environments. - Past experience at an early-stage company where you built deployment operations, playbooks, and tooling. - Familiarity with observability and incident management in distributed systems (Prometheus, Grafana, Datadog, or similar). - Experience with CI/CD pipeline design, deployment automation, or infrastructure self-service tooling for enterprise customers. 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 through Carrot - Lunch, as well as delicious snacks and coffee to keep you energized  - 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 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 even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.

Location: Sydney Workplace: Hybrid 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. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. 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, 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 through Carrot - Lunch, as well as delicious snacks and coffee to keep you energized  - 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 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 even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.

Location: United Kingdom Role Title: Self Employed Mortgage Advisor Company: CMME Mortgages & Protection Ltd (OneDome) Join one of the fastest -growing mortgage brokerage firms in the UK as a self-employed mortgage advisor. Are you a high-performing mortgage advisor looking to maximize your revenue potential? Would you like to have a guaranteed payout when you retire or exit? Join us and become part of a top UK financial services firm! CMME is an established, directly authorized mortgage brokerage firm based in Hampshire. We have been trading successfully since 2004 and are one of the largest mortgage brokerages in the UK. CMME became a part of the OneDome Group in 2023. OneDome Group owns two property listing websites;Onedome.com and Nethouseprices.com, as well as a wealth manager. As a member of our team, you will have access to the following: The highest pay-away rate in the market from a Directly Authorized company Guaranteed exit value for your business when you retire Access to our unique propositions like HomeBuyer Service (mortgage and conveyancing bundled together) Our cutting-edge technology platform Full compliance and marketing support Connection to a large network of estate agency introducers Help with business development Mortgage admin support What do we expect? You have a strong track record as an employed or self-employed mortgage advisor You are self-sufficient and have an ambition to grow Sstrong sales skills Client service is paramount for you Strong communication skills Self-motivated Responsibilities: To provide a mortgage advice service to clients. Identify and contact potential clients. Gather sufficient client information and identify client needs. Analyse information gathered and undertake sufficient research to make suitable recommendations. Complete all supporting documentation in an accurate manner. Ensure that the level of service, as agreed with each client, is delivered in a timely manner. Attain and maintain competent status as defined by the FCA and the firm. Keep up to date with new products, technical or legislative changes within the marketplace. Always comply with the Compliance and Training & Competence Schemes/Procedures of the firm. Always comply with the requirements of the Financial Services and Markets Act 2000 and the FCA’s Principles, Rules and the Code of Practice for Approved Persons. Maintain performance standards in accordance with those outlined in the Key Performance Indicators section of the firm’s Training & Competence scheme. Via self-assessment and feedback, identify Continuing Professional Development (CPD) needs to maintain and enhance Competent status and undertake appropriate activity to meet those needs. Salary: £100,000 – £120,000 / year

Location: Sydney 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. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. 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 through Carrot - Lunch, as well as delicious snacks and coffee to keep you energized  - 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 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 even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.

Location: Sydney 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. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. WHAT YOU'LL DO - Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity. - Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations. - Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, address objections, and close deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders. - Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers' needs. Collaborate with our marketing team to implement effective sales campaigns and presentations. - Help define our sales motion: We’re an early team, and your work will directly impact how our GTM function operates and succeeds. - Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical, and operations orgs to deliver our industry-leading product. WHAT YOU'LL BRING - 10+ years of experience in an enterprise customer-facing sales role, identifying and closing large accounts. - Enterprise experience: Experience managing a $1M+ quota and running end-to-end complex deals. - Strong communication skills: Exceptional verbal and written communication abilities. - Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions. - Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling. EVEN BETTER... - Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends. - Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early-stage growth. 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 through Carrot - Lunch, as well as delicious snacks and coffee to keep you energized  - 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 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 even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.

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. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. WHAT YOU’LL DO - Act as a primary point of accountability for customer trust enablement, including participation in customer meetings, security reviews and AI governance. - Contribute to AI Governance including building guardrails to align with AI regulations (EU AI Act, ISO 42001, NIST AI RMF and local EU laws). - Partner closely with Legal and Privacy to interpret regulatory requirements and support complex, security-sensitive contractual discussions, escalating risks and tradeoffs appropriately. - Collaborate with Engineering and Product to ensure expectations are reflected in system design and operational effectiveness. - Translate regulatory and privacy expectations into scalable, region-aware technical controls across model governance, agent security and safety, and data handling. - Own and evolve customer-facing trust materials and narratives related to AI, privacy, and security. - Represent Sierra in customer audits and formal assessments, clearly explaining security posture, governance decisions, and risk management approaches. - Support resilience and response expectations as part of broader governance, with an emphasis on learning and continuous improvement. - Continuously improve trust by identifying opportunities to streamline workflows, increase automation, and improve signal quality, while maintaining a high bar for accuracy and quality. WHO YOU’LL WORK WITH You will act as a strategic partner to Platform, Security, Product, Agent Development, Legal, and GTM, ensuring security and compliance requirements are embedded into architecture decisions, product roadmaps, and go to market execution while supporting product velocity and technical complexity. WHAT YOU’LL BRING - 8+ years of experience in security compliance, privacy, or regulatory roles in SaaS, fintech, or AI companies. - Deep experience with EU regulatory frameworks, including GDPR, DORA, EU AI Act and emerging AI regulations, paired with strong awareness of US and APAC regulatory norms. - Demonstrated ability to operate globally understanding where requirements must diverge and where alignment is possible. - Experience engaging directly with enterprise and regulated customers as a trusted representative of security, privacy, and compliance. - Ability to translate abstract or evolving regulatory requirements into defensible, real-world practices. - Comfort operating in ambiguity, making reasoned judgment calls, and clearly articulating rationale and tradeoffs. - Strong written and verbal communication skills, including close collaboration with Legal and external stakeholders. EVEN BETTER... - Direct experience preparing for or operationalizing DORA, EU AI Act or ISO/IEC 42001. - Experience working in and/or supporting fintech or AI companies globally - Familiarity with AI governance frameworks such as NIST AI RMF or CSA AI controls. - Experience navigating cross-border data transfer, residency, and localization consideration in a multi-cloud environment. - Prior experience in customer-facing, sales-adjacent, or deal-support contexts. - Experience automating global security and compliance workflows. 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 through Carrot - Lunch, as well as delicious snacks and coffee to keep you energized  - 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 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 even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.

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. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. WHAT YOU'LL DO - Build enterprise-grade AI agents: As an Agent PM at Sierra, you will be responsible for partnering directly with our engineers and customers to build and ship AI agents that handle thousands of customer conversations a day. - Engage with customers: In the role, you will engage with all levels of our customers’ businesses: - Discover and assess their requirements. - Prepare and present demonstrations of Sierra’s agent. - Address and overcome technical challenges in the business process by working with technical counterparts. - Develop and improve Sierra virtual agents to fit and anticipate our customers’ needs and business processes. - Become trusted advisors and drive strategic technical strategies for our customers. - Shape the product roadmap: Work with Sierra’s engineering and product development teams to scope and implement new features essential to the success of your customers. WHAT YOU'LL BRING - 5-7+ years experience in product development of highly technical products. - Past experience in Product Management or other similar product development roles at or above the level of Senior Product Manager. - Experience crafting and tailoring a message for potential customers, including executives. - Ability to communicate highly technical concepts to both non-technical and technically proficient audiences, including recent AI developments. - Degree in a technical or related field, or equivalent professional experience. EVEN BETTER... - AI-related experience (experience with product development for AI agents a plus). - Some coding experience with React, Typescript, and Go. - MBA or equivalent professional experience (while this is a product management role, you will have the opportunity to lean into broader business roles). - Past roles that interface with end customers to influence software development. 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 through Carrot - Lunch, as well as delicious snacks and coffee to keep you energized  - 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 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 even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.

Location: London, United Kingdom About OneDome: OneDome is a fast-growing property and fintech ecosystem, revolutionizing the homebuying journey by integrating mortgages, conveyancing, and financial services into a seamless digital experience. As we continue our ambitious growth strategy through acquisitions, we are seeking a dynamic Integration Project Manager to drive the successful onboarding and integration of newly acquired firms. Role Overview: The Integration Project Manager will be responsible for leading and executing post-merger integration projects, ensuring smooth transitions for acquired firms into OneDome’s ecosystem. The role involves close collaboration with cross-functional teams, acquired company leadership, and external stakeholders to streamline operations, align business processes, and maintain strategic objectives. Key Responsibilities: Project Management: Develop and manage detailed integration plans, timelines, and deliverables for each acquisition. Cross-Functional Coordination: Work with Finance, HR, IT, Compliance, and Operations teams to ensure a seamless transition. Process Alignment: Identify gaps in existing processes and implement best practices to align acquired businesses with OneDome’s operating model. Stakeholder Communication: Serve as the central point of contact for internal and external stakeholders during integration. Risk & Issue Management: Identify potential risks and roadblocks, proactively addressing challenges to ensure a smooth transition. Change Management: Support cultural and operational alignment, ensuring minimal disruption to employees and customers. Performance Tracking: Define KPIs and report on integration progress, identifying areas for continuous improvement. Requirements: Experience: 3+ years of project management experience, preferably in M&A integrations, fintech, real estate, or financial services. Project Management Skills: Strong experience in leading post-merger integration, business transformation, or operational restructuring projects. Stakeholder Management: Ability to work across different business units, manage expectations, and influence senior leadership. Problem-Solving: Hands-on, solutions-oriented approach to tackling integration challenges. Communication Skills: Excellent verbal and written communication skills, with the ability to present complex issues clearly. Technical Proficiency: Familiarity with CRM systems, finance tools, project management software Certification: PMP, PRINCE2, or similar qualifications are advantageous. Industry Knowledge: Understanding of mortgage brokerage, fintech, property services, or financial compliance is a plus. What We Offer: Competitive salary & performance-based bonus Career progression in a high-growth, acquisition-driven environment Opportunity to shape the integration strategy of a fast-scaling fintech company Salary: £55,000 – £70,000 / year

Location: Toronto 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. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. 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 through Carrot - Lunch, as well as delicious snacks and coffee to keep you energized  - 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 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 even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.

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. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. 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 - Build enterprise-grade AI agents for healthcare: As an Agent PM at Sierra, you will be responsible for partnering directly with our engineers and customers to build and ship AI agents that handle thousands of customer conversations a day. These agents help people understand their coverage, find providers, schedule appointments, navigate billing, and more—all while maintaining strict HIPAA compliance and the trust that healthcare demands. - Discover where agents will make an impact: Ground-up discovery is a critical part of the role. Work closely with providers, payers, RCMs and pharmaceutical companies to identify new use cases and opportunities for AI Agents to deliver impact for their business. You should be our customer’s trusted advisor, and be able drive strategic decisions for our customers. - Engage with customers: In the role, you will engage with all levels of our customers’ businesses: - Discover and assess their requirements. - Prepare and present demonstrations of Sierra’s agent. - Address and overcome technical challenges in the business process by working with technical counterparts. - Develop and improve Sierra virtual agents to fit and anticipate our customers’ needs and business processes. - Become trusted advisors and drive strategic technical strategies for our customers. - Shape the platform and healthcare roadmap: Your direct work with healthcare 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 in healthcare. EXAMPLE PROJECTS These are examples of projects our healthcare team has worked on: - Develop net new agentic healthcare products that can cut costs and drive revenue in the healthcare ecosystem. - Build AI agents for major health insurance networks that handle detailed questions like "what's my co-pay for a primary care visit?" and "how many physical therapy sessions do I have left?" - Develop voice and chat agents for nonprofit healthcare providers that help members find in-network specialists, check availability, and locate providers based on specialty or location - Create AI agents for multi-site primary and urgent care providers that manage appointments and answer common questions across 30+ clinics - Build agents that replace lengthy paper intake forms with conversational experiences, boosting pre-visit intake conversion rates - Develop AI agents for healthcare financial platforms that help patients understand billing, payment status, explanations of benefits, and financial assistance eligibility. - Experiment with the latest voice models and integrate them at scale for healthcare enterprises requiring secure, compliant phone interactions WHAT YOU'LL BRING - 5-7+ years experience in product development of highly technical products. - Past experience in Product Management or other similar product development roles at or above the level of Senior Product Manager. - Experience crafting and tailoring a message for potential customers, including executives. - Ability to communicate highly technical concepts to both non-technical and technically proficient audiences, including recent AI developments. - Degree in a technical or related field, or equivalent professional experience. - Genuine interest in healthcare and improving patient/member experiences EVEN BETTER... - Experience in healthcare technology, health IT or working with healthcare organizations - Understanding of healthcare compliance requirements (HIPAA, PHI handling and healthcare data privacy) - AI-related experience (experience with product development for AI agents a plus). - Some coding experience with React, Typescript, and Go. - MBA or equivalent professional experience (while this is a product management role, you will have the opportunity to lean into broader business roles). - Past roles that interface with end customers to influence software development. 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 through Carrot - Lunch, as well as delicious snacks and coffee to keep you energized  - 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 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 even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.

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. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. WHAT YOU’LL DO - Lead the design and delivery of production-grade AI agents: You’ll manage and grow a team of engineers building highly performant, reliable, and intuitive AI agents that are central, mission-critical, and directly drive Sierra’s growth. These aren’t prototypes—they are powerful, scalable systems running in production environments across industries like finance, healthcare, and commerce. You’ll ensure technical excellence, operational reliability, and high customer impact. - Own the Agent Development Life Cycle (ADLC): You’ll guide your team through the full lifecycle—from initial pilot through deployment and continuous iteration—coaching engineers to set and maintain the standard for ADLC best practices. You’ll ensure projects are delivered on time, meet customer needs, and scale effectively in production environments. - Partner with large enterprises and cutting-edge startups: You’ll collaborate with leaders at some of the world’s largest enterprises to understand their most pressing business challenges, and guide your team in building AI agents that transform how they operate at scale. You’ll also work with innovative startups in Europe, embedding AI agents across their entire business stack to drive innovation and efficiency. - Shape the future of the platform: Your team’s direct work with customers will guide the evolution of Sierra’s core platform. You’ll surface unmet needs, prioritise initiatives, and collaborate with research, product, and platform teams to shape the future of AI agent development and Sierra’s product. WHAT YOU'LL BRING - Experience leading engineering teams that build and scale end-to-end production systems - Strong technical problem-solving skills and the ability to guide teams through ambiguous, fast-changing environments - A leadership style that blends high standards with empathy, fostering both speed and quality - Proven ability to work closely with customers and translate business needs into technical deliverables - Excellent communication skills across technical and non-technical audiences - Degree in Computer Science or related field, or equivalent professional experience. EVEN BETTER... - AI-related experience (experience developing AI agents a plus). - Experience building or deploying AI/LLM systems in production - Background as a founder, engineering lead, or startup builder with high ownership and urgency - Familiarity with tools for today’s AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering - Prior experience with React, TypeScript, and/or Go - Experience interfacing with customers or leading 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 through Carrot - Lunch, as well as delicious snacks and coffee to keep you energized  - 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 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 even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.

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. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. WHAT YOU'LL DO - Own independent audits and regulatory programs including ISO 42001, PCI DSS, NIST 800-53, FedRAMP, HIPAA, and related frameworks. - Drive scope definition, readiness assessments, auditor engagement, remediation planning, and executive level reporting. - Develop a strong working understanding of Sierra’s Conversational AI Platform, model providers, and cloud architecture. Partner with Platform and Agent Engineering to design and operationalize controls across multi cloud environments, infrastructure, inference and data platforms. - Build a centralized and evolving security controls library mapped to compliance, regulatory and customer requirements. Continuously assess control effectiveness, identify gaps, prioritize risk, and drive remediation that strengthens Sierra’s security and compliance posture. - Define and enforce security baselines for cloud infrastructure, containerized workloads, Kubernetes, identity, encryption, logging, and network security controls. Partner with engineering teams to integrate security requirements into configuration and change management. - Design and operate automated compliance workflows using AI, infrastructure as code, and security tooling to reduce manual effort, improve control assurance, and scale with platform evolution. WHO YOU’LL WORK WITH You will act as a strategic partner to Platform, Product, Agent Development, Legal, and GTM, ensuring security and compliance requirements are embedded into architecture decisions, product roadmaps, and go to market execution while supporting product velocity and technical complexity. WHAT YOU’LL BRING - 8+ years of experience in security compliance or GRC or security adjacent roles within fast growing technology companies. - Deep expertise in security compliance frameworks including ISO 42001, PCI DSS, NIST 800-53, FedRAMP, and similar regulatory environments. - A systems oriented and engineering focused GRC mindset, with the ability to reason about cloud architecture, data flows, and control effectiveness alongside engineers. - Experience owning complex audits and driving risk based remediation across distributed teams. - Hands-on experience with multi-cloud infrastructure (AWS, Azure, GCP). - Strong experience implementing and automating security controls across cloud infrastructure, configuration management, container security, Kubernetes, encryption, identity, and authentication systems. - Ability to clearly communicate compliance requirements internally to engineering teams and externally to customers in a technically credible way. - Relevant certifications such as CISSP, CISA, PCI ISA, ISO 27001 Lead Auditor, or equivalent experience. EVEN BETTER... - Experience supporting AI platforms, fintech, healthcare, or other highly regulated environments. - Familiarity with global regulatory environments including GDPR, DORA, the EU AI Act, and emerging security and AI governance requirements across APAC regions. - Experience supporting public sector or FedRAMP aligned environments. WHY JOIN US? You will operate at the center of AI systems, cloud infrastructure, and global compliance, shaping how security controls are designed and scaled for modern AI platforms. This role offers high ownership, deep technical partnership with engineering, and the opportunity to define what strong GRC looks like at Sierra. 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 through Carrot - Lunch, as well as delicious snacks and coffee to keep you energized  - 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 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 even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.

Location: United States; Los Angeles, United States Salesperson / Hard Money Loan Closer Who We Are LBC Mortgage is a direct private lender specializing in Hard Money, Bridge, DSCR, and Rehab loans across the U.S. We move fast, structure smart deals, and close when others can’t. Our reputation is built on execution, relationships, and results. If you’re a true closer who knows Hard Money inside out — this role is for you. Who You Are You are not “learning” Hard Money. You’ve closed deals , handled tough borrowers, structured creative solutions, and know how to move files from lead → approval → funding without babysitting. You thrive on: Fast timelines Complex deals High commissions Clear accountability What You’ll Do Close Hard Money loans from start to finish — no hand-holding Work directly with brokers, investors, and repeat clients Structure deals creatively to get them funded Drive volume through follow-ups, urgency, and relationship management Collaborate closely with processing and underwriting to push files to the finish line Build a strong personal pipeline while growing LBC’s production Maintain clean, professional communication and CRM records What You Must Have Proven experience closing Hard Money loans (this is mandatory) Strong understanding of LTV, ARV, rehab budgets, and investor strategies Confidence handling objections and tight timelines Ability to manage multiple deals at once without losing momentum Professional, polished communication with brokers and clients What We Offer Aggressive commission structure (for real closers only) Strong underwriting & processing support Fast decisions, direct access to leadership Remote position — work from anywhere A high-performance culture that rewards results, not excuses This Role Is NOT For You If: You’ve never closed a Hard Money deal You need heavy training or micromanagement You’re uncomfortable with pressure, pace, or accountability Ready to Close? If you’re a producer , not a talker — and Hard Money is your comfort zone — we want to hear from you.

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. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. WHAT YOU’LL DO - Write the playbook for onboarding and educating customers onto Sierra – both the Agent SDK and Agent Studio, our no-code platform. - Lead the creation and execution of developer training and enablement programs. - Build content that scales — including technical documentation, educational videos, onboarding paths, and sample repositories for SDK adoption. - Develop and deploy AI Agents as an Agent Software Engineer, building the knowledge to become a world-leading expert on agent development. - Work with our marketing teams to publish developer case studies and success stories to inspire and connect our growing technical community. - One important aspect of this role is presenting educational content to customers, both live and on video. If you have recordings of any presentations you've given in the past, add links to one or two of your favorites here. WHAT YOU'LL BRING - Passion for helping customers across small and large enterprises learn to build exceptional AI Agents. - Degree in Computer Science or related field, or equivalent professional experience. - 4+ years of experience in hands-on software development of highly technical products or developer relations roles. - Excellent written and verbal communication skills and a desire to apply them in hands-on training sessions. - Desire, excitement, and enthusiasm for building an in-person, global community around developing AI Agents. - Strong technical skills and familiarity with modern software development — especially developer tooling, SDKs, and APIs. - Demonstrated experience in designing and executing technical training, certification, or community initiatives. EVEN BETTER... - Previous experience developing agents using open source tools like LangGraph or interacting with MCP servers. - Familiarity with agent platforms, developer communities, or early-stage developer product ecosystems. - Proficiency with TypeScript, and comfort with writing code in collaboration with agents like Claude, Codex or Cursor - Experience collaborating across product, engineering, and go-to-market teams to launch strategic initiatives. 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 through Carrot - Lunch, as well as delicious snacks and coffee to keep you energized  - 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 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 even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.

Location: Bridgetown, Barbados Career Opportunity – Attorney-at-Law – Associate Due to our continued growth and success across the Caribbean, Dentons is seeking to add an Associate in our Barbados office to join our talented team of attorneys and other professionals. Dentons is the world’s largest law firm established in over 80 countries and with over 160 offices worldwide.  We are the most ranked and recognized pan-Caribbean law firm by Chambers & Partners as well as Legal 500 covering 14 jurisdictions throughout the region with a 15th to be added later this year. As a member of our Dentons team, one will not only be exposed to some of the more interesting work to flow through the region but also be part of an integrated team operating across the Caribbean, working beyond the shores of your home island in a cross-border capacity, and with the opportunity to collaborate with our colleagues across the globe.  Dentons is a fast-paced environment but rewarding both personally and professionally for the appropriate applicants. The role will support the Partner and Head of Real Estate in the Property & Real Estate department. To be effective in this role, you will need to provide exceptional service to our clients, display excellent time management and organizational skills, and attend to the legal needs of the Firm and team in a quick and efficient manner.  A strong candidate for this role is a professional individual who is efficient, organized and detail oriented. The incumbent’s responsibilities will include but not be limited to the following: Effectively communicating with both clients and Attorneys in a timely and efficient manner. Drafting, review, negotiation and settlement of contracts and other documents related to real estate sales and acquisitions, Drafting, review, negotiation and settlement of leases and mortgages for real estate developments, hotel and commercial projects Competently and efficiently managing real estate transactions from start to completion. Conducting legal research. Working on other matters within the firm’s practice areas should the need arise. Requirements The ideal candidate should possess a Law Degree, Legal Education Certificate and at least five (5) years of post-qualification experience: Possess CARICOM Skilled National Status. Strong and varied experience in property and real estate law. Ability to work as part of a team locally, regionally, and globally while embracing innovation and technology. Capacity to appreciate international standards and the expectations of the Firm’s global client base. Have excellent interpersonal, oral and written communication skills. Be able to handle various matters working in fast paced environment with tight deadlines. Have a keen eye for detail. Have excellent interpersonal, oral and written communication skills. All suitably qualified persons interested in this exciting opportunity, should send their Curriculum Vitae with full details of their experience, achievements and qualifications together with the names and contact details of two business references to recruitment.barbados@dentons.com , no later than March 1, 2026 .

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. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. WHAT YOU'LL DO - Implement Go-to-Market software for our marketing, sales, and agent development teams - Design and build the automated workflows, integrations, and AI-powered systems that turn signal into pipeline, across enrichment, scoring, routing, and outbound activation - Own our enrichment infrastructure end-to-end: the pipelines that take a new signup, demo request, or event attendee list and return a fully enriched, scored, Salesforce-upserted record across Clay, ZoomInfo, Cognism, and LLM-powered sources - Build AI agents and AI-powered internal tools that compound sales team output — account research, call summarization, RFP and security questionnaire response, proposal generation, and Slack-accessible agents that surface account intel on demand - Build and improve the fit scoring pipeline that evaluates every account against our ICP and writes results to Postgres and Salesforce, including signal design, batching, retry logic, and continuous improvement of the underlying models - Develop data architecture using Postgres, Fivetran pipelines, and reverse ETL. Keep data jobs healthy and in sync with the tools that consume them; track downstream impact when schemas and apps change - Ship production code with PR review, observability, and proper error handling and debug production incidents (Salesforce platform failures, enrichment failures, LLM timeouts) WHAT YOU'LL BRING - 3+ years in GTM Engineering, Revenue Operations, Sales Engineering, Growth Engineering, or a closely adjacent technical role at a high-growth B2B SaaS company - Python and TypeScript skills: You write clean code, understand async patterns, can design a database schema, and can debug a production incident from logs alone - Hands-on experience inside a modern GTM stack (Salesforce, HubSpot, Outreach, Clay, enrichment providers): You understand how leads flow through a CRM and why data quality degrades over time - Production experience with LLMs: Prompt design, eval loops, error handling, and the difference between a demo and a system you can trust at scale - Strong working knowledge of SQL, schemas, and data flow across GTM and warehouse systems - Systems thinking: You’ve built data pipelines and think about what happens at 10x volume, when an API goes down, or when the same account hits your queue five times in parallel - Owner's mindset: You take accountability from code to deployment to adoption, define scope with minimal direction, and ship good solutions over perfect ones EVEN BETTER… - Built applications using LLMs, ideally with exposure to production-grade AI/ML systems - Developed custom Salesforce solutions using apex classes, apex triggers, LWC, SLDS - Integrated salesforce with other business systems using REST/SOAP APIs, Platform Events, and External Services 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 through Carrot - Lunch, as well as delicious snacks and coffee to keep you energized  - 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 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 even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.

Location: US - Remote; San Francisco, CA; New York, NY; Atlanta, GA Workplace: Remote 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. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. WHAT YOU'LL DO - Lead & develop a high-performing sales team: Hire, onboard, and develop AEs across your region, Coach reps on deal strategy, pipeline management, and execution. Create a culture of accountability, learning, and collaboration. Identify and grow future leaders on your team. - Own regional performance: Own your regional number and forecast accuracy, Inspect pipeline quality and help unblock stalled deals. Drive consistent execution of our sales process. Partner with RevOps to ensure clean data and clear insights. - Be deeply involved in deals: Join key customer and prospect conversations. Help reps navigate complex buying committees and late-stage deals. Support pricing, negotiation, and close strategy. WHAT YOU'LL BRING - 10-15+ years of experience: Extensive experience in enterprise customer-facing sales role, identifying and closing large accounts. - People leadership experience: 5+ years managing, mentoring, and developing a high-performing enterprise sales team. - Enterprise experience: You've run and managed end-to-end complex deals ($1M+). - Strong communication skills: Exceptional verbal and written communication abilities. - Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions. EVEN BETTER... - Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends, as well as fluency with AI tooling and workflows. - Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early stage growth. 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 through Carrot - Lunch, as well as delicious snacks and coffee to keep you energized  - 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 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 even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.

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. Our co-founders are Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google's earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace. SOFTWARE ENGINEER, SECURITY Security Engineering builds the foundations that let Sierra deliver powerful AI agents while protecting customer data and trust. We partner across product and platform to make security, privacy, and safety core product capabilities and secure defaults.   WHAT YOU’LL DO Our work spans several security domains. You’ll go deep where your strengths and interests are strongest, with opportunities to explore new areas alongside the team. Build the Foundations of Trust. Design and ship systems that make Sierra’s platform secure by default — spanning agent safety/security, privacy, identity, authentication, authorization, and data security. You’ll work across all layers of production (agents, infrastructure, backend, frontend) to embed security-conscious design into the core of our product. Own Cross-Cutting Systems. Partner with product and platform teams to implement and evolve Sierra’s trust primitives: identity management, access control, auditability, and data lifecycle management. You’ll make pragmatic design trade-offs between usability, performance, and security. Secure Agentic AI Systems. Build controls that ensure AI agents can't leak customer data, execute unauthorized actions, or be manipulated into unintended behavior. Design runtime policy enforcement for tool use, implement safe agent sandboxing, and create boundaries that protect data while keeping agents powerful and useful. Automate and Scale Security-Adjacent Workflows. Create developer-friendly tooling to reduce risk and friction — whether through automating security checks in CI/CD, enforcing privacy boundaries through schema validation, or instrumenting runtime monitoring for sensitive events.   WHAT YOU’LL BRING Strong Software Engineering Skills. Experience building and maintaining production systems. You’re comfortable designing APIs, integrating with authentication or identity frameworks, and thoughtfully using AI-assisted development tools to build, test, and ship high-quality code faster without lowering the quality bar. Security Mindset. You think like a security engineer — considering how data flows, where it’s stored, who can access it, and how to design for least privilege and transparency. Product and Platform Mindset. You care about building secure scalable systems that enable, not block, innovation. You work closely with product teams to make trade-offs clear and help them move quickly without sacrificing trust. Curiosity and Ownership. You take ambiguous, cross-cutting problems from first principles to production and go deep when needed: tracing an authorization decision from agent intent through policy enforcement and downstream effects, or following sensitive data across model context, logs, storage, and tenant boundaries. You define the problem, align partners, ship the solution, and own it in production. EVEN BETTER IF… - You’ve worked on privacy, identity, trust & safety, authN/authz, or data protection systems. - You’ve built security frameworks, libraries, or tooling that developers actually use or integrated security automation into CI/CD pipelines. - You have exposure to AI systems or care about designing secure-by-default LLM applications. - You think like an attacker — you naturally ask "what could go wrong?" when reviewing designs or while building systems. You've found or fixed real security issues in production systems. - You thrive in 0→1 environments, where foundational systems have to balance speed, reliability, and trust.   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 through Carrot - Lunch, as well as delicious snacks and coffee to keep you energized  - 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 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 even if your experience doesn't precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.