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Location: London Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU’LL DO - Support our Sales, Marketing, and customer-facing teams, which might include: - Driving end-to-end GTM processes, including building pricing proposals, developing customer presentations, and delivering financial analyses to enable team success. - Analyzing, optimizing, and implementing sales territories and processes for a fast-growing sales team. - Building out prospecting programs, marketing campaigns and events cadences, helping the sales team to drive net new demand. - Help define and scale the playbook for how Sierra builds, evaluates, launches, and expands AI agents at large enterprises. - Take on special projects and initiatives related to international expansion, pricing, marketing, legal, deal strategy, and agent development - Work with Pricing, Legal, Operations, Sales, Agent Development & Finance teams to identify inefficiencies in current GTM operations and design solutions to help Sierra scale. - Turn insight into action: Analyze complex datasets and translate findings into clear, executive-ready recommendations that drive high-leverage decisions. - Serve as a versatile, proactive team player, taking on both foundational tasks and high-impact strategic initiatives that drive the GTM team’s success. - Leverage AI-native tools such as Claude Code, Cursor, and Codex to build lightweight internal systems, automate workflows, and create operational leverage. WHAT YOU’LL BRING - 4+ years of experience in revenue operations, sales operations, management consulting, corporate strategy, or business operations. - Proficiency in financial modeling and data analysis (e.g., Excel, Google Sheets); experience with data visualization tools (e.g., Tableau, Looker, or Power BI). - A detail-oriented, methodical, and process-driven mentality that is focused on both accuracy and efficiency. - Demonstrated ability to manage multiple projects, prioritize effectively, and meet deadlines. - A proactive mindset with the ability to navigate ambiguity, drive and execute initiatives, and deliver results in a fast-paced, dynamic environment. - Strong written and verbal communication skills, with the ability to distill complex ideas and problems into straightforward, actionable recommendations, especially to executives. EVEN BETTER… - SQL experience. - Familiarity with CRM platforms (e.g., Salesforce, HubSpot) and marketing automation tools. - Previous 0-1 startup or operational experience. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: San Francisco, CA; US - Remote; New York, NY; Atlanta, GA Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. ABOUT THE HEALTHCARE TEAM - Our healthcare agents already reach over 50% of U.S. families. We partner with leading health plans, providers, and healthcare platforms to deliver AI agents that handle some of the most sensitive and high stakes conversations in any industry. From helping members understand their benefits to resolving billing questions with empathy, our healthcare agents are transforming how patients and policyholders interact with the healthcare system. - Our healthcare customers include major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms. - Join us to transform the patient experience across the healthcare system—and help build technology that makes care more accessible, more human and more affordable for everyone. WHAT YOU'LL DO - Be the primary partner to your Sales counterparts helping to win deals and grow customers - Go from first discovery to a tailored, working agent in days, not weeks, across prospects and existing customers - Work with every team involved in the decision: CX, IT, security, procurement, and executive sponsors - Own the end-to-end technical pre-sales process by scoping customer use cases, articulating business value, designing and demoing Sierra’s incredible platform, leading technical and architecture reviews, and serving as the trusted technical expert throughout the sales cycle - Mentor newer SEs and contribute reusable assets for your industry or team - Stay with the account after the sale, through the Agent Development handoff, launch, and expansion to new use cases - Go deep on your industry, the patterns, and winning motions to scale your work WHAT YOU'LL BRING - 4-6+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales - Experience in leading the sales process with large Enterprise customers with deal sizes ranging $500-$1M - Past experience in demo building, and presenting, and working with customers or clients in the GTM function - Experience in relationship-building with prospects, including executives and technical leaders - Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience - Ability to leverage AI tools efficiently as a regular part of your technical sales motion — discovery prep, solution design, demo and prototype building, technical proposals. Importantly, you own the accuracy of anything you put in front of a customer, whether or not AI helped you build it - Experience growing accounts past initial sale - Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience EVEN BETTER... - Experience translating code, technical logic and user requirements to product and engineering requirements - Selling a technical AI product OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: San Francisco, CA; US - Remote; New York, NY; Atlanta, GA Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. ABOUT THE FINANCIAL SERVICES TEAM - Our financial services customers span systemically important banks, neobanks committed to building more delightful banking software (1 in 3 of the world's leading banks use Sierra!), insurers that provide protection for life’s most challenging moments, vertically integrated ecosystems like Rocket Companies, and more. The decisions we make impact millions of end customers and billions of dollars in economic activity. - Our financial services team partners closely with these organizations to set their AI strategies and build modern tools that carefully handle moments when a person’s private anxiety meets an institution’s procedural muscle - the instant before a family learns whether they are pre-approved for a mortgage; the claustrophobic half hour after someone notices a fraudulent charge; the frustrating experience of losing a card and needing to order a new one. - Sierra’s Financial Services team is transforming the customer experience and building technology that makes the industry more accessible, human, and affordable for everyone. WHAT YOU'LL DO - Be the primary partner to your Sales counterparts helping to win deals and grow customers - Go from first discovery to a tailored, working agent in days, not weeks, across prospects and existing customers - Work with every team involved in the decision: CX, IT, security, procurement, and executive sponsors - Own the end-to-end technical pre-sales process by scoping customer use cases, articulating business value, designing and demoing Sierra’s incredible platform, leading technical and architecture reviews, and serving as the trusted technical expert throughout the sales cycle - Mentor newer SEs and contribute reusable assets for your industry or team - Stay with the account after the sale, through the Agent Development handoff, launch, and expansion to new use cases - Go deep on your industry, the patterns, and winning motions to scale your work WHAT YOU'LL BRING - 4-6+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales - Experience in leading the sales process with large Enterprise customers with deal sizes ranging $500-$1M - Past experience in demo building, and presenting, and working with customers or clients in the GTM function - Experience in relationship-building with prospects, including executives and technical leaders - Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience - Ability to leverage AI tools efficiently as a regular part of your technical sales motion — discovery prep, solution design, demo and prototype building, technical proposals. Importantly, you own the accuracy of anything you put in front of a customer, whether or not AI helped you build it - Experience growing accounts past initial sale - Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience EVEN BETTER... - Experience translating code, technical logic and user requirements to product and engineering requirements - Selling a technical AI product OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: London Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU’LL DO - Design, build, and deliver enablement programs that drive productivity across our fast-growing European sales and sales engineering teams, including supporting new hire onboarding cohorts as they ramp in seat, in region. - Use AI tools to create content faster, run AI-driven role-play and call coaching, and give sellers self-serve answers to their questions. - Own training on the tools EMEA sellers and SEs use daily for account research, call prep, call recaps, pipeline updates, and drafting outreach and proposals. - Teach sellers when to trust AI output, how to verify it, and how to handle customer data under EU privacy and regulatory requirements (GDPR, EU AI Act), so every seller can explain, demo, and stand behind how Sierra uses AI with customers. - Create playbooks and programs, track adoption and impact (tool usage, time saved, ramp speed, deal velocity), and report results to EMEA and global sales leadership. Turn the best field practices into shared prompts, playbooks, and workflows for the global enablement team. - Localize and launch global sales plays in EMEA (flagging any that don’t translate), collect field feedback for the global Programs Lead, and support regional launches with Sales Leadership and Marketing. WHAT YOU’LL BRING - 5+ years in sales enablement at a B2B software company, with exposure to both onboarding and plays - Experience adapting centrally built programs for a regional audience - Evidence of leadership: prior people management, or leading projects and mentoring others, and a genuine interest in leading a team - Credibility with senior sales leaders and experienced sellers and SEs, and a strong facilitator - Hands-on, daily use of AI tools in your own work, and experience teaching others to adopt new tools and change how they work - Comfortable working independently with a team several hours behind you EVEN BETTER… - Experience in AI or enterprise software - Additional European languages - Experience as the first enablement hire in a region - Experience hiring or building a team - Experience running an AI fluency or AI tooling program for a sales team - Familiarity with the EU AI Act or GDPR as they apply to how sales teams use AI OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: Europe, US Company Intro At Toloka AI we create data that powers leading GenAI models and innovations. We work with frontier labs, big tech, renowned AI startups, enterprises and non-profit research organizations worldwide. We use a combination of Experts + Crowd + Tech Platform to teach AI models to reason and evaluate their efficacy and safety. We have experts in more than 50 different domains—from doctors and lawyers to physicists and engineers—and boast one of the most diverse global crowds, representing over 100 countries and speaking 40+ languages. We are a well-funded startup with an enviable portfolio of clients including Anthropic, Amazon, Microsoft, poolside, Recraft, and Shopify. Recently, we secured strategic investment led by Bezos Expeditions with participation from Mikhail Parakhin, CTO of Shopify and board advisor to leading GenAI companies, who now serves as our Chairman of the Board. Our remote-first team is globally distributed around the world: USA, UK, the Netherlands, Serbia, and more. We are headquartered in Amsterdam. About the position We are seeking an exceptional Delivery Lead to own the successful execution of complex AI data projects across a portfolio of clients. This is a hands-on role combining project leadership, client management, and operational excellence to ensure projects are delivered to the highest standards of quality, on time, and within target margins. As a Delivery Lead, you will manage virtual, cross-functional teams and coordinate engineers, supply managers, researchers, science teams, product teams, and other internal functions as required. You will work closely with clients to understand their requirements, manage expectations, resolve issues, and ensure delivery consistently meets or exceeds expectations. The role requires someone who can operate comfortably at both the strategic and operational level, taking ownership of the overall delivery outcome while being prepared to get into the detail when required. Key Responsibilities Own end-to-end delivery across a complex portfolio of projects, taking ultimate accountability for data quality, timelines, client outcomes, unit economics, gross margin, and transparent stakeholder reporting. Lead cross-functional delivery teams and project managers, ensuring projects remain on track, risks and issues are proactively identified and resolved, and stepping in as a hands-on Delivery Project Manager when required. Drive operational excellence across the delivery function, overseeing planning, resource allocation, internal and external communication, project reporting, status updates, retrospectives, and execution standards. Partner closely with Business Development to scope new opportunities, shape project proposals, optimize delivery models, and successfully transition prospects into high-quality, commercially viable engagements. Build strong client relationships throughout project execution, managing complex technical stakeholders, maintaining clear communication, addressing delivery challenges, and ensuring outcomes that drive client satisfaction and retention. Drive team performance and continuous improvement , motivating delivery teams, identifying opportunities to increase efficiency, improving processes and workflows, and developing new approaches to enhance execution quality. Lead the adoption of delivery improvements , rolling out new processes, tools, and ways of working across the organization while gathering feedback, measuring impact, and continuously refining the delivery model. Required Skills Proven experience in the AI space , particularly within startups, including working with clients and managing teams or projects at scale. Experience managing complex projects including discovery, decomposition, scope planning, implementation and adoption Client facing experience ; a consulting background reaching levels of Engagement Manager or Associate Partner Deep understanding of AI and GenAI : technology and market trends, basic knowledge of statistics, ML and data science, data generation Background in STEM : BS or MS in computer science, maths, physics, etc. What we can offer You will be part of an international, dynamic environment that drives innovation and sets new standards in the AI and technology sector. Competitive compensation package. Flexible, fully remote schedule. Work at the leading edge of AI development, alongside a dedicated and dynamic team of experts. Projects with customers that are AI industry leaders and well-known household names Equal Opportunity Employer Toloka is committed to providing equal opportunity and fostering an inclusive environment. We welcome applications from all qualified individuals and do not discriminate on the basis of race, religion, color, national origin, sex, sexual orientation, gender identity, age, marital status, veteran status, disability, or any other characteristic protected by applicable law. Selection decisions are made based on qualifications, merit, and business need. [Important Notice] Scam Alert Regarding Fake Job Postings It has come to our attention that an individual or group is fraudulently impersonating Toloka to post fake jobs and solicit personal information from applicants. Please be aware: Official Communication: Our recruiting team will only contact you from an official " toloka.ai " email address. We will NEVER use Gmail, Yahoo, Tolokainc, toloka.inc, or other personal or seemingly business email accounts. Our Process: We will never ask for your bank account details, credit card number, or any fees as part of the application or interview process. Official Listings: All legitimate job openings are posted on our official careers page: https://toloka.ai/careers#job-list What to do: If you see a suspicious job posting or have been contacted by someone you suspect is a scammer, please do not provide any personal information. Instead, report the incident to us directly at security@toloka.ai and report the profile/post to LinkedIn. We are taking this matter very seriously and are working with the appropriate parties to resolve it. Thank you for your vigilance! To learn how we collect, use, disclose, and store personal data, check out our Privacy Notice .

Location: New York, NY Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU'LL DO - Serve as a trusted partner to several customer-facing leaders across Sierra’s Sales and Agent Development organization, providing comprehensive, high-touch executive support. - Proactively manage complex calendars, meetings, travel, and expenses across multiple leaders, balancing internal priorities with customer commitments. - Coordinate customer meetings, executive briefings, and external engagements, ensuring each interaction is thoughtfully prepared and executed. - Anticipate scheduling conflicts, changing needs, and competing priorities, resolving issues independently and keeping commitments moving forward. - Coordinate domestic and international travel, with careful attention to itineraries, accommodations, agendas, logistics, and preparation. - Partner with leaders and their teams to make meetings effective by preparing materials, developing agendas, tracking action items, and coordinating follow-ups. - Collaborate closely with Executive Assistants and cross-functional partners across Sierra to coordinate priorities and ensure alignment across the organization. - Build strong working relationships with teams across product, engineering, operations, and other functions. - Support recruiting coordination, team operations, and other administrative needs as the organization grows. - Plan and execute team events, including leadership meetings, off-sites, hackathons, and team travel. - Establish and continuously improve administrative systems and processes that support multiple leaders and a rapidly scaling organization. - Handle sensitive information, technical roadmaps, personnel matters, and strategic communications with confidentiality and discretion. WHAT YOU'LL BRING - 5+ years of Executive Assistant or similar strategic support experience. - Demonstrated ability to support multiple customer-facing senior leaders simultaneously while adapting to different communication styles, priorities, and working preferences. - Experience supporting technical, product, or engineering leaders in a fast-paced environment. - Strong customer orientation and the ability to interact with customers and external stakeholders with professionalism, responsiveness, and sound judgment. - Exceptional attention to detail and a proactive mindset, with a commitment to creating polished and seamless experiences for leaders, customers, and internal partners. - Excellent organizational and time-management skills, with the ability to shift priorities quickly while remaining accurate and proactive. - Proven ability to operate independently, anticipate needs, and make sound judgment calls on behalf of leadership. - Strong relationship-building skills and the ability to partner effectively with cross-functional teams and external stakeholders. - High integrity and discretion when handling confidential or sensitive information. - Advanced proficiency with Google Workspace and Slack, along with the ability to learn new tools quickly. - Willingness and ability to work on-site in San Francisco four days per week. EVEN BETTER... - Experience in a fast-growing, in-person start-up environment. - Experience working with C-suite executives. - Experience working within a dual, floating, or team-based Executive Assistant structure. - Experience managing complex travel, executive events, and high-touch on-site logistics. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: New York, NY; San Francisco, CA Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU'LL DO As Sierra’s founding Technical Program Manager for Enterprise Cloud Deployments, you’ll help define how we bring our AI platform into the cloud environments of some of the world’s largest and most regulated enterprises. Working alongside Agent Engineers, Deployed Infrastructure Engineers, and Agent Strategists, you’ll own the programs & strategy that take customers from deployment planning to agents live in production, and continue to support the upgrades and expansion that follow. You’ll bring your technical program management expertise to enterprise AI while establishing the playbooks and ways of working that help this new function scale. - Own the end-to-end program plan for a customer's in-VPC (Bring Your Own Cloud, BYOC) deployment. Translate customer requirements into a clear deployment plan, with clear workstreams, owners, milestones, and dependencies across Sierra and customer teams. - Keep the customer's teams (platform engineering, cloud provisioning, security, networking, model access) aligned and moving, and clear blockers before they hit the launch date. - Be the translation layer between our engineers and the customer's: define requirements such as model access, observability, and upgrade cadence, and turn technical discussions into actionable next steps. - Run the operating cadence (standups, weekly status, escalations) so leadership and working groups on both sides always know where the project stands. - Partner with Sierra's Platform and Deployed Infrastructure teams to feed customer-specific learnings back into our standard deployment offering, runbooks, and tooling, making each subsequent launch more predictable and repeatable. - Define the TPM function at Sierra as we scale & establish the playbooks, operating rhythms, and standards that future TPMs and customer teams will build on. WHAT YOU'LL BRING - 4+ years in technical program management, infrastructure or platform program management, deployment or solutions engineering, or a similar role where you were accountable for delivering complex technical projects across multiple teams. - A track record of bringing structure to complex technical programs, with strong attention to detail and the follow-through to turn plans into results. - A strong technical foundation from infrastructure, platform, or complex backend programs. You can work through technical dependencies with engineers, understand how requirements such as networking, permissions, and provisioning affect delivery, and translate those discussions into a clear plan. You’ll deepen your knowledge of Sierra’s architecture and customer deployment environments as you ramp. - Technical curiosity: you learn new systems quickly, ask thoughtful questions, build context, and apply what you learn to move programs forward. - Comfort operating inside large, complex enterprise organizations (change management, security reviews, ownership spread across many teams) with the persistence and resourcefulness to keep teams aligned and deployments moving. - Clear, structured communication: you make complex technical topics, program status, and decisions understandable to engineers and leaders, and adapt your approach to your audience. - Degree in Computer Science, Engineering, or a related field, or equivalent professional experience. EVEN BETTER… - Hands-on engineering background (software, DevOps, SRE, or infrastructure) before moving into program or product management, or direct experience with AWS, VPCs, IAM, Kubernetes, or Terraform. - Experience deploying software into customer-owned cloud environments (BYOC, VPC, or air-gapped), especially at banks or other regulated institutions. - Familiarity with LLM infrastructure: model gateways, Bedrock or Azure OpenAI, observability for AI systems. - Experience at an early-stage company where you built the program-management function from scratch. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: San Francisco, CA; New York, NY Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. What you'll do As an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai Lead, 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. We believe the best leaders stay hands-on and close to the work. You'll 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 and the team you lead. - Lead the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Our leads operate as ICs for their first 2-4 months at Sierra, then evolve into the lead role, all while continuing to take agents from initial scope through conversation design, tooling, evaluation, launch, and continuous iteration in production. You'll both build directly and guide your team through the full lifecycle, coaching strategists to set and maintain the standard for ADLC best practices. You'll ensure agents launch on time, meet customer needs, and measurably move the customer's business. - Build the team as you build the business. You’ll take on two kinds of leadership: serving as the senior sponsor on our key customer deployments, and managing a team of strategists. You'll drive how the strategist function grows, from hiring and onboarding to defining what success looks like. - 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 actively build/shape the AI strategy that gets them there. You'll develop your team to do the same. - Guide delivery with the customer's working teams day to day. Run working sessions, troubleshoot agents as issues come up, and coach your team to make the calls that keep every build on track for launch. You'll be accountable for delivery quality and customer impact across your team's portfolio. - Shape the future of the product. Your team's direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prioritize initiatives, and collaborate with research, product, and platform teams to influence where Sierra goes next. 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, plus the ability to develop that muscle in others. - 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 guide teams through fast-changing, ambiguous environments. - A leadership style that comes from being hands-on. You blend high standards with empathy, fostering both speed and quality across your team. - 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, as well as leading teams that run, multiple complex, high-visibility projects at once and driving them to outcomes. - 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. 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. - Background as a founder, product or strategy leader, or startup operator with high ownership and urgency. - Experience managing teams in product, consulting, solutions, or other customer-facing roles. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

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

Location: Dubai, United Arab Emirates PipeCare Group of companies has been helping the customers ensure the integrity of their pipeline and facility assets for over 20 years. PipeCare Group is looking for an experienced Executive Personal Assistant to provide executive and business support to the Chairman. Job Description: Reporting directly to the Chairman, the Executive Personal Assistant provides executive and administrative support while taking an active role in coordinating the Chairman’s business activities. The role requires managing multiple priorities, coordinating directly with management and external parties, following up on the Chairman’s instructions and deadlines, and taking ownership of assigned matters through to completion. If you are a professional who thinks ahead, understands quickly, takes initiative, and knows how to get things done, this is the right role for you. This position will suit an energetic, responsible, and resourceful professional who enjoys a varied role, works confidently and independently, and takes real ownership of their work. Roles and Responsibilities • Manage and organize the Chairman’s calendar, appointments, priorities, and schedule. • Organize complex international travel, including flights, accommodation, transportation, itineraries, meetings, and required travel documentation. • Prepare meeting agendas, presentations, reports, correspondence, briefing materials, and supporting documentation. • Manage incoming communications and requests addressed to the Chairman, identify priorities, obtain necessary information, and coordinate the appropriate action or response. • Track the Chairman’s instructions, commitments, action points, and deadlines, and follow up with responsible parties to ensure timely execution. • Coordinate with senior management and internal departments on matters requiring the Chairman’s attention or involvement. • Communicate with external stakeholders, including Board members, clients, business partners, advisers, and other senior-level contacts. • Draft, edit, and format executive correspondence, emails, presentations, reports, and other business communications. • Maintain the Chairman’s contacts, records, documents, and relevant business information. • Organize executive meetings and business visits, ensuring the necessary arrangements are in place. • Handle sensitive and confidential business matters with professional discretion. • Support special assignments from the Chairman and coordinate their execution. Qualification Requirements: • Excellent written and spoken English, with strong business writing and communication skills. • Strong organizational and time-management skills with excellent attention to detail. • Ability to effectively use AI tools and task management systems to organize work, manage priorities, track progress, and achieve assigned goals. • Sound judgement and the ability to identify priorities and respond effectively to changing requirements. • Confident and professional communication skills when dealing with senior management and external stakeholders. • Proactive and solution-oriented approach, with the ability to anticipate requirements and address issues effectively. • Ability to perform effectively in a fast-paced, demanding, and international business environment. Education and Experience Requirements • Bachelor’s degree is required; Master’s degree or relevant postgraduate qualification will be considered a strong advantage. • Minimum of 5 years of relevant experience supporting a Chairman, CEO, C-level executive, business owner, or other senior executive. • Experience within an international, engineering, industrial, or project-driven organization will be considered an advantage. • Advanced proficiency in Microsoft Outlook, Word, Excel, PowerPoint, Teams, and Adobe Acrobat. • Proven experience organizing complex international travel and executive-level meetings. • Flexibility to work outside standard business hours when required by executive schedules, international operations, travel, or urgent business matters.

Location: San Francisco, CA Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU'LL DO As a Software Engineer on Sierra’s Cloud Infrastructure team, you’ll own the foundation that every Sierra customer runs on. That includes our multi-tenant environments, where most of our customers and data live, and our isolated single-tenant environments for highly regulated enterprises. Sierra is expanding quickly across AWS and GCP, in regions across North America, Europe, and Asia-Pacific. We expect to roughly double our number of deployments over the next year. The work is very visible. Our deployments support the relationship with major customers, so you’ll see directly how your infrastructure affects customers and the business. Our challenges keep evolving, from scaling, reliability, and new compliance and regulations. ON THIS TEAM, YOU WILL: - Design, build, and operate Sierra’s cloud infrastructure across AWS and GCP (and soon Azure) using Terraform and Kubernetes. - Simplify and standardize our deployments so that adding a new region or environment is repeatable and predictable. We want to treat deployments like cattle, not pets. - Stand up and operate new multi-tenant regions and single-tenant environments for customers with strict regulatory or isolation needs. - Help build and run compliant environments, including our FedRAMP deployment. - Own and improve deploys and releases across our fleet, investing in tooling and developer experience so engineers can ship quickly and safely. - Build security guardrails that give enterprise customers confidence in our shared multi-tenant environment. - Work with our BYOC (Bring Your Own Cloud) team to make Sierra easy to deploy into customers’ own cloud environments. - Drive reliability across the platform through observability, incident response, root cause analysis, and postmortems. - Write production code, mostly in Go, to automate infrastructure and replace manual work with durable systems. WHAT YOU'LL BRING - 6+ years of hands-on software or infrastructure engineering experience, including building and operating production systems at scale. - Broad infrastructure experience on at least one major cloud (AWS, GCP, or Azure). Breadth and fundamentals matter more than expertise in one specific cloud. - Deep expertise in at least one layer of the stack, such as compute, orchestration, networking, or deploys, plus a real interest in owning the layers next to it. - Hands-on experience with infrastructure as code (Terraform preferred) and container orchestration (Kubernetes). - Strong coding skills and a bias toward automation and tooling. Go experience is a plus. - A pragmatic, scrappy approach. You can start with a rough prototype and evolve it into production ready. - Curiosity and flexibility. You adapt to new clouds, tools, and customer requirements instead of forcing every problem into one familiar pattern. - A degree in Computer Science or a related field, or equivalent professional experience. EVEN BETTER - Experience running infrastructure across multiple clouds and many regions or environments. - Experience with compliance-driven environments (FedRAMP, SOC 2, HIPAA, or financial services). - Experience building deploy systems, CI/CD, or internal developer platforms. - Experience deploying software into customer-managed cloud environments. - An SRE background, or experience leading reliability and incident management programs. - Experience with distributed databases such as DynamoDB or Spanner. - Experience at a fast-paced startup or on a small infrastructure team with broad scope. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: San Francisco, CA Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU'LL DO: - As an Executive Assistant supporting the leadership function at Sierra, you will provide a wide range of strategic and administrative support to our General Counsel and our Partnerships leaders. - Proactively manage several leaders' calendar, travel, and meetings. - Collaborate with leaders and team members to ensure meetings are effective by sending preparation materials, following up on action items, and serving as a knowledgeable resource on relevant topics or organizational matters. - Draft team and external correspondence on behalf of the leader. Liaise with internal staff and external stakeholders, building and maintaining strong relationships on behalf of the leader. - Maintain a high level of confidentiality and discretion with all materials and information. - Plan and execute internal events (in-person and virtual), including team offsites, trainings, and team travel. Book travel and hotel accommodations, negotiating contracts as needed. - Establish new—and improve existing—administrative systems and processes as part of Sierra’s founding admin team. WHAT YOU'LL BRING: - 5+ years of Executive Assistant or similar experience. - Ability to build relationships and partner effectively with cross-functional teams and external partners. - Excellent time management skills, willingness and ability to quickly shift tasks and priorities, and anticipate the needs of others before they arise. - Ability to organize, analyze, and prioritize executive workflows, often interpreting and leveraging data. - Willingness and ability to be in the San Francisco office 4 days per week and ability to travel with leaders if needed (~est 1x per quarter). - Advanced proficiency with Google Suite & Slack. EVEN BETTER... - Experience in a fast-growing, in-person start-up environment. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: San Francisco, CA; US - Remote; New York, NY; Atlanta, GA Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. ABOUT THE RETAIL TEAM - Sierra is partnering with a large and growing number of retailers - spanning apparel and beauty, grocery and big-box, home and auto, consumer services, marketplaces, and consumer technology. Our agents help millions of shoppers and members every day: tracking and returning orders, finding the right product, booking services, and resolving issues in each brand’s own voice. - Retail is also where AI agents go beyond support to generate revenue. From product discovery and personalized recommendations to cart recovery, win-back campaigns, and in-store support that turns unanswered store calls into visits and sales, our team is redefining what an agent can do for a brand’s top line - not just its cost line. - Join us to transform how the world’s most-loved consumer brands engage their customers - and help build technology that makes shopping more personal, effortless, and delightful for everyone. WHAT YOU'LL DO - Go deep on a few accounts. Learn each customer's business well enough that you could be wearing their badge in their hallways - Own the end-to-end technical pre-sales process by scoping customer use cases, articulating business value, designing and demoing Sierra’s incredible platform, leading technical and architecture reviews, and serving as the trusted technical expert throughout the sales cycle - Decide when to bring in Agent Development, Product, Security, Legal, and Sierra leaders, and what each of them needs to do. You keep everyone aimed at the same goal - Raise the bar for the SE team: mentor others, set standards for demos and pilots, and write the playbooks for Strategic deals and GTM processes - Stay with the account after the sale, through the Agent Development handoff, launch, and expansion to new use cases - Share what you see across your largest accounts with Product leadership and inform roadmap WHAT YOU'LL BRING - 7+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales - Experience in leading the sales process with Strategic customers with deal sizes of $1M+ consistently - Past experience in demo building, and presenting, and working with customers or clients in the GTM function - Strong experience in relationship-building with prospect stakeholders, including C-suite executives and technical leaders - Experience leading architecture, integration, and security discussions with enterprise architects, engineering leaders, and security teams - Ability to leverage AI tools efficiently as a regular part of your technical sales motion — discovery prep, solution design, demo and prototype building, technical proposals. Importantly, you own the accuracy of anything you put in front of a customer, whether or not AI helped you build it - Experience growing accounts past initial sale and defining customer roadmaps to facilitate growth - Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience EVEN BETTER... - Experience translating code, technical logic and user requirements to product and engineering requirements - Selling a technical AI product OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: San Francisco, CA; US - Remote; New York, NY; Atlanta, GA Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU'LL DO - Go deep on a few accounts. Learn each customer's business well enough that you could be wearing their badge in their hallways - Own the end-to-end technical pre-sales process by scoping customer use cases, articulating business value, designing and demoing Sierra’s incredible platform, leading technical and architecture reviews, and serving as the trusted technical expert throughout the sales cycle - Decide when to bring in Agent Development, Product, Security, Legal, and Sierra leaders, and what each of them needs to do. You keep everyone aimed at the same goal - Raise the bar for the SE team: mentor others, set standards for demos and pilots, and write the playbooks for Strategic deals and GTM processes - Stay with the account after the sale, through the Agent Development handoff, launch, and expansion to new use cases - Share what you see across your largest accounts with Product leadership and inform roadmap WHAT YOU'LL BRING - 7+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales - Experience in leading the sales process with Strategic customers with deal sizes of $1M+ consistently - Past experience in demo building, and presenting, and working with customers or clients in the GTM function - Strong experience in relationship-building with prospect stakeholders, including C-suite executives and technical leaders - Experience leading architecture, integration, and security discussions with enterprise architects, engineering leaders, and security teams - Ability to leverage AI tools efficiently as a regular part of your technical sales motion — discovery prep, solution design, demo and prototype building, technical proposals. Importantly, you own the accuracy of anything you put in front of a customer, whether or not AI helped you build it - Experience growing accounts past initial sale and defining customer roadmaps to facilitate growth - Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience EVEN BETTER... - Experience translating code, technical logic and user requirements to product and engineering requirements - Selling a technical AI product OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: 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. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU'LL DO - Go deep on a few accounts. Learn each customer's business well enough that you could be wearing their badge in their hallways - Own the end-to-end technical pre-sales process by scoping customer use cases, articulating business value, designing and demoing Sierra’s incredible platform, leading technical and architecture reviews, and serving as the trusted technical expert throughout the sales cycle - Decide when to bring in Agent Development, Product, Security, Legal, and Sierra leaders, and what each of them needs to do. You keep everyone aimed at the same goal - Raise the bar for the SE team: mentor others, set standards for demos and pilots, and write the playbooks for Strategic deals and GTM processes - Stay with the account after the sale, through the Agent Development handoff, launch, and expansion to new use cases - Share what you see across your largest accounts with Product leadership and inform roadmap WHAT YOU'LL BRING - 7+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales - Experience in leading the sales process with Strategic customers with deal sizes of $1M+ consistently - Past experience in demo building, and presenting, and working with customers or clients in the GTM function - Strong experience in relationship-building with prospect stakeholders, including C-suite executives and technical leaders - Experience leading architecture, integration, and security discussions with enterprise architects, engineering leaders, and security teams - Ability to leverage AI tools efficiently as a regular part of your technical sales motion — discovery prep, solution design, demo and prototype building, technical proposals. Importantly, you own the accuracy of anything you put in front of a customer, whether or not AI helped you build it - Experience growing accounts past initial sale and defining customer roadmaps to facilitate growth - Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience EVEN BETTER... - Experience translating code, technical logic and user requirements to product and engineering requirements - Selling a technical AI product OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: 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. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU'LL DO - Be the primary partner to your Sales counterparts helping to win deals and grow customers - Go from first discovery to a tailored, working agent in days, not weeks, across prospects and existing customers - Work with every team involved in the decision: CX, IT, security, procurement, and executive sponsors - Own the end-to-end technical pre-sales process by scoping customer use cases, articulating business value, designing and demoing Sierra’s incredible platform, leading technical and architecture reviews, and serving as the trusted technical expert throughout the sales cycle - Mentor newer SEs and contribute reusable assets for your industry or team - Stay with the account after the sale, through the Agent Development handoff, launch, and expansion to new use cases - Go deep on your industry, the patterns, and winning motions to scale your work WHAT YOU'LL BRING - 4-6+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales - Experience in leading the sales process with large Enterprise customers with deal sizes ranging $500-$1M - Past experience in demo building, and presenting, and working with customers or clients in the GTM function - Experience in relationship-building with prospects, including executives and technical leaders - Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience - Ability to leverage AI tools efficiently as a regular part of your technical sales motion — discovery prep, solution design, demo and prototype building, technical proposals. Importantly, you own the accuracy of anything you put in front of a customer, whether or not AI helped you build it - Experience growing accounts past initial sale - Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience EVEN BETTER... - Experience translating code, technical logic and user requirements to product and engineering requirements - Selling a technical AI product OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: San Francisco, CA; US - Remote; New York, NY; Atlanta, GA Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU'LL DO - Be the primary partner to your Sales counterparts helping to win deals and grow customers - Go from first discovery to a tailored, working agent in days, not weeks, across prospects and existing customers - Work with every team involved in the decision: CX, IT, security, procurement, and executive sponsors - Own the end-to-end technical pre-sales process by scoping customer use cases, articulating business value, designing and demoing Sierra’s incredible platform, leading technical and architecture reviews, and serving as the trusted technical expert throughout the sales cycle - Mentor newer SEs and contribute reusable assets for your industry or team - Stay with the account after the sale, through the Agent Development handoff, launch, and expansion to new use cases - Go deep on your industry, the patterns, and winning motions to scale your work WHAT YOU'LL BRING - 4-6+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales - Experience in leading the sales process with large Enterprise customers with deal sizes ranging $500-$1M - Past experience in demo building, and presenting, and working with customers or clients in the GTM function - Experience in relationship-building with prospects, including executives and technical leaders - Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience - Ability to leverage AI tools efficiently as a regular part of your technical sales motion — discovery prep, solution design, demo and prototype building, technical proposals. Importantly, you own the accuracy of anything you put in front of a customer, whether or not AI helped you build it - Experience growing accounts past initial sale - Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience EVEN BETTER... - Experience translating code, technical logic and user requirements to product and engineering requirements - Selling a technical AI product OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: San Francisco, CA; US - Remote; New York, NY; Atlanta, GA Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. ABOUT THE RETAIL TEAM - Sierra is partnering with a large and growing number of retailers - spanning apparel and beauty, grocery and big-box, home and auto, consumer services, marketplaces, and consumer technology. Our agents help millions of shoppers and members every day: tracking and returning orders, finding the right product, booking services, and resolving issues in each brand’s own voice. - Retail is also where AI agents go beyond support to generate revenue. From product discovery and personalized recommendations to cart recovery, win-back campaigns, and in-store support that turns unanswered store calls into visits and sales, our team is redefining what an agent can do for a brand’s top line - not just its cost line. - Join us to transform how the world’s most-loved consumer brands engage their customers - and help build technology that makes shopping more personal, effortless, and delightful for everyone. WHAT YOU'LL DO - Be the primary partner to your Sales counterparts helping to win deals and grow customers - Go from first discovery to a tailored, working agent in days, not weeks, across prospects and existing customers - Work with every team involved in the decision: CX, IT, security, procurement, and executive sponsors - Own the end-to-end technical pre-sales process by scoping customer use cases, articulating business value, designing and demoing Sierra’s incredible platform, leading technical and architecture reviews, and serving as the trusted technical expert throughout the sales cycle - Mentor newer SEs and contribute reusable assets for your industry or team - Stay with the account after the sale, through the Agent Development handoff, launch, and expansion to new use cases - Go deep on your industry, the patterns, and winning motions to scale your work WHAT YOU'LL BRING - 4-6+ years experience in Sales Engineering, Solutions Engineering or customer-facing technical sales - Experience in leading the sales process with large Enterprise customers with deal sizes ranging $500-$1M - Past experience in demo building, and presenting, and working with customers or clients in the GTM function - Experience in relationship-building with prospects, including executives and technical leaders - Ability to connect a prospect’s specific business problems and Sierra’s solutions and explain them to both a technical and non-technical audience - Ability to leverage AI tools efficiently as a regular part of your technical sales motion — discovery prep, solution design, demo and prototype building, technical proposals. Importantly, you own the accuracy of anything you put in front of a customer, whether or not AI helped you build it - Experience growing accounts past initial sale - Bachelor's Degree or above; bonus if in Computer Science or related field, or equivalent professional experience EVEN BETTER... - Experience translating code, technical logic and user requirements to product and engineering requirements - Selling a technical AI product OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.