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Location: United States 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 position We're seeking a Freelance AI Data Project Manager who will join our Delivery team and will build, drive and maintain our client’s solutions. Joining us in this role means you will lead a virtual cross-functional team managing successful project implementation. This involves both client communication and internal coordination. The team consists of talented engineers of different kinds, supply managers and other departments on an ‘as needed’ basis. This is a key role for us to ensure we deliver the best possible experience for our clients and enable us to constantly grow our business. Example Projects SFT (supervised fine tuning) data generation pipeline producing thousands of prompts and completions weekly across several languages and domains of knowledge; Evaluation pipeline helping to estimate LLMs’ responses quality and reaching a throughput of hundred thousands weekly; A red-teaming project helping to collect malicious prompts of different kinds to ensure models’ safety. Key Responsibilities Take ultimate ownership for all delivery team projects, including data quality, delivery timelines, unit economics and overall transparency for stakeholders; Lead a cross-functional delivery team ensuring projects are on track, any issues and risks are highlighted and resolved proactively; Own operations of the delivery team: including internal and external communication, activities planning, posting summaries and status updates, conducting retros etc.; Drive and motivate the team, seek out change to increase the organization’s efficiency; Help roll out improvements to the delivery team focussing on increased adoption and providing feedback for further improvements. Qualifications Experience leading technical cross-functional teams ; Experience managing complex projects including discovery, decomposition, scope planning, implementation and adoption; Client facing experience ; Being generally agile, able to switch quickly to new domains and subjects; Consulting , Tech , Competitors background is a big plus; Good understanding of LLMs and their life cycle in particular; Experience in data generation ; Experience and proactiveness in suggesting process changes is appreciated; Proven experience in the AI space , including working with clients and managing teams or projects at scale. What we can offer Full-time independent contractor engagement (B2B) through the Ontop contractor platform , working via your own company or business entity; Flexible, fully remote schedule ( 40 hours per week ); 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; Friendly community. [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: San Francisco, CA; New York, NY Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. ABOUT THE TECH, MEDIA & TELECOM TEAM - We work with some of the world's most influential and recognizable companies, from global telecommunications providers and leading media brands to technology platforms that power businesses worldwide. - We build agents for the moments that matter, helping our customers rise to the occasion when service disruptions, major product launches, or global events like the World Cup https://www.linkedin.com/posts/claybavor_at-sierra-we-are-very-proud-to-have-partnered-activity-7491200203899760641-I27d?utm_source=share&utm_medium=member_desktop&rcm=ACoAABYjELMBZfjrg-wrv53M1tVXGe93FF3eTww drive millions of customer interactions. - We bring Sierra’s Horizon https://sierra.ai/product/horizon vision to TMT by building agents that transform the entire customer relationship: - Telecommunications: Turn one of the most frustrating customer experiences into one of the most personal, with agents that understand each subscriber, optimize their plan and savings, anticipate opportunities to add value, and earn their loyalty over time. - Media: Turn every subscription into an ongoing, personalized relationship, with agents that help each subscriber get the most from their experience through the right content, offer, plan, and support from their free trial through retention. - Technology: Bring the white-glove customer experience traditionally reserved for the largest enterprise accounts to every customer, helping them adopt the product, discover new ways to get value, expand their usage, and successfully renew. 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: - Create agents that pursue goals over weeks and months, reasoning about when to reach out, which channel to use, and what next action will move a customer relationship forward. - Develop personalization and experimentation systems powered by Sierra's Context Engine https://sierra.ai/blog/context-engine that combine customer data, behavior, prior conversations, and real-time context to determine the right offer or experience, then learn from every interaction and experiment to autonomously improve personalization over time. - Design conversational discovery agents that reason across huge content catalogs and rich subscriber context, using interests, history, entitlements, and the moment at hand to help someone quickly find something they'll actually want to watch, read, or listen to. - Build agents that troubleshoot deeply integrated telecommunications and connected-device experiences, reasoning across account, billing, network, and device systems to diagnose issues and take the actions needed to resolve them. - Experiment with new voice experiences and Voice Personas https://sierra.ai/blog/introducing-voice-personas tailored to each brand, customer, and moment, bringing the right empathy, energy, and conversational style to everything from navigating a frustrating telecom billing issue to helping someone discover their next favorite show or find the plan that's right for them. 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. - Excitement in the Tech, Media & Telecom space and a care for helping some of the world’s top brands continue to build brand loyalty with their customers. 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: San Francisco, CA; 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 TRAVEL, TRANSPORTATION AND HOSPITALITY TEAM - The Travel, Transportation and Hospitality (TTH) supports some of the largest airlines, hotel chains, rental car brands, cruise lines and travel tech companies in the world. Our customers are frontiers in the travel space, and are true thought partners in shaping our platform, helping reinvent what hospitality looks like in this new era. Our customers rely on us to not only deliver standout customer experiences, driving stronger growth in their business. - Our TTH team is constantly pushing the bounds of what is possible within this industry and beyond. We help support our customers in the moments that matter — whether that’s proactively encouraging new bookings to prepare for exciting events, or helping guests rebook their flights or stays during times of distress. We help our customers maximize the lifetime value of their guests and build products to delight guests at every touchpoint. - We’re a small and scrappy team, and we support each other with any deliverables we have to meet. Every engineer on TTH is also a product-led thinker; every PM on TTH is tinkering and developing tangible prototypes; and every strategist on TTH is capable of owning an agent end to end. As a part of this team, you’ll set the standard on what it means to go beyond your role, and help build the travel industry of the future. 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: - Building innovative multimodal experiences: Spearhead cross-cutting initiatives, partnering with the voice and Experience SDK teams to bring to life embedded voice mode in mobile apps. This brand new product allows users to talk, tap and text with our agents all in a single view — unlocking communication through rich visualizations, and accuracy in input collection with chat, with the ease and efficiency of voice. - Shipping complex booking experiences: Build personalized booking flows, including leveraging Google Maps APIs to support searching for properties via an embedded map view, developing a recommendation engine based on past reservations and orchestrating seamless payment collection to complete the full booking lifecycle. - Abstracting complex systems into packages: Modernize legacy reservations systems by creating Sierra packages that optimize querying and updating trips for customers across the board. You’ll be challenged to think deeply about how to orchestrate each step of these workflows to maximize efficiency while upholding reliability and accuracy. - Improving the capabilities of our built in integrations: Expand platform extensibility by introducing new capabilities to our existing integrations. An example is extending our MCP integrations to support MCP UI, which allows customers to dynamically host their custom UI resources on our embedded chat windows. 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. - Excitement in the travel space and a genuine care for helping improve the guest experience as a whole. Our customers care deeply about their guests, and we carry that through what we build every day. EVEN BETTER... - Language Fluency: Professional fluency in both Spanish and English. - 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: San Francisco, CA; 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 insurers that provide protection for life’s most challenging moments, systemically important banks, neobanks committed to building more delightful banking software, 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 hours after a family discovers their home has been damaged by a wildfire and begins filing a claim; the difficult conversation following the loss of a loved one as beneficiaries navigate a life insurance claim; the frustration of dropping a phone, shattering the screen, and trying to quickly understand coverage and arrange for a repair or replacement. - 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 - 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 insurance companies that consistently outperform human agents in filing claims quickly and consistently. - Develop and refine AI agents capable of navigating complex customer interactions, like generating a quote for insuring a modified 1960s Corvette. - 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. - Genuine interest in Financial Services and improving the end customer experience. Experience in insurance technology, implementations at financial institutions, working inside of these institutions or familiarity with financial services security and compliance requirements (coverage advice, PII handling, etc.) are a strong plus. 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: San Francisco, CA; New York, NY; Atlanta, GA; 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. ABOUT THE RETAIL TEAM - The Retail team on Agent Engineering supports some of the largest and most storied consumer brands in the world – including Uber, Wayfair, Wilson, and Sonos. Together, we’re reinventing what commerce looks like in this new, AI-first era. Our customers rely on us to not only deliver novel experiences, but also host hundreds of millions of shopper and vendor interactions across web, app, phone, and in-store channels every year. - Our team supports our customers’ customers in the moments that matter – whether that's guiding a shopper to the right product during a limited drop or a Black Friday surge, locating a package that never arrived, or troubleshooting an appliance that stopped working. Always true to each brand’s voice, we create seamless experiences that resolve issues, drive revenue, increase lifetime value, and build lasting loyalty. - Our team supports our customers' customers in the moments that matter most, from product discovery and checkout to order tracking and troubleshooting. Always true to each brand’s voice, we create seamless experiences that resolve issues, drive revenue, increase lifetime value, and build lasting loyalty. - Every engineer on the Retail Team is a product-led thinker; every PM on Retail is also tinkering and developing tangible prototypes; and every strategist on Retail is capable of owning an agent end to end. As a part of this team, you'll set the standard on what it means to go beyond your role, and help build the groundwork for the retail industry in the future. 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: - Abstracting complex commerce systems into packages: Modernize the sprawl of order management, fulfillment, returns, and warranty systems behind the large retailer ecosystem by creating scalable packages that optimize looking up and updating orders for customers – from Shopify storefronts to decades-old homegrown Order Management System (OMS) and claims platforms. - Shipping the full discovery-to-checkout lifecycle: Build personalized shopping flows that carry a shopper from a vague idea to a completed order. This includes everything from building a recommendation engine that combines transcript-aware planning, structured filters, and semantic and keyword search to payment and order placement. - Building production-grade agents at a truly global scale: Sierra’s retail agents serve some of the world’s largest global brands, handling traffic at unprecedented volumes during the busiest times of the year and across all geographic locales. You will be building at the frontier of enterprise applied AI. 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. - Excitement in the retail space and a care for helping some of the world’s top brands continue to build brand loyalty with their customers. 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: San Francisco, CA; 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 - 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. - Genuine interest in Financial Services and improving the end customer experience. Experience in financial technology, implementations at financial institutions, working inside of these institutions or familiarity with financial services security and compliance requirements (fair lending, PII handling, etc.) are a strong plus. EVEN BETTER... - Experience building or deploying AI/LLM 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: 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. ABOUT THE HEALTHCARE TEAM - Our healthcare agents already reach over 50% of U.S. families. We partner with leading health plans, providers, and healthcare platforms to deliver AI agents that handle some of the most sensitive and high stakes conversations in any industry. From helping members understand their benefits to resolving billing questions with empathy, our healthcare agents are transforming how patients and policyholders interact with the healthcare system. - Our healthcare customers include major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms. - Join us to transform the patient experience across the healthcare system—and help build technology that makes care more accessible, more human and more affordable for everyone. WHAT YOU'LL DO - Design and deliver production-grade AI agents for healthcare: You'll build and ship highly performant, reliable, and empathetic AI agents that handle sensitive patient and member interactions. These agents help people understand their coverage, find providers, schedule appointments, navigate billing, and more—all while maintaining strict HIPAA compliance and the trust that healthcare demands. - Drive the 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 serving healthcare payers, providers, and platforms. - Partner with healthcare leaders: You'll work directly with executives and technical teams at health plans, provider networks, and healthcare technology companies to understand their most pressing challenges - from managing high call volumes to reducing administrative burden and building AI agents that transform how they operate at scale. - Navigate healthcare complexity: You’ll develop deep expertise in healthcare systems and workflows, including integrations across EHR and patient access platforms, payer and provider operations, and common healthcare data and interoperability standards. You’ll become fluent in the nuances of benefits and eligibility, claims and billing, scheduling and intake, and translate that understanding into exceptional, trustworthy AI experiences. - Build the future of the platform: Your direct work with healthcare customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prototype new tools and features, and collaborate with research, product, and platform to shape the future of AI agent development in healthcare. EXAMPLE PROJECTS These are examples of projects our healthcare team has worked on: - Build AI agents for major health insurance networks that handle detailed questions such as, "What's my co-pay for a primary care visit?" and "How many physical therapy sessions do I have left?" - Develop voice and chat agents for healthcare providers that help members find in-network specialists, check availability, and locate providers based on specialty or location; - Create AI agents for multi-site primary and urgent care providers that manage appointments and answer common questions across 30+ clinics; - Build agents that replace lengthy paper intake forms with conversational experiences, boosting pre-visit intake conversion rates; - Develop AI agents for healthcare financial platforms that help patients understand billing, payment status, explanations of benefits, and financial assistance eligibility - all while maintaining HIPAA compliance and strong PHI/data privacy safeguards. - Experiment with the latest voice models and integrate them at scale for healthcare enterprises requiring secure, compliant phone interactions; 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. - Genuine interest in healthcare and improving patient/member experiences. EVEN BETTER... - Experience in healthcare technology, health IT or working with healthcare organizations - Familiarity with healthcare systems: Major EHR ecosystems (e.g., Epic, Cerner/Oracle Health, athenahealth); X12 EDI transactions and clearinghouse workflows; scheduling/patient access, practice management, and contact center platforms. - Understanding of healthcare compliance requirements (HIPAA, PHI handling and healthcare data privacy). - 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.

Задачи: — Разработка и внедрение ML/NLP решений для реальных продуктовых задач. — Работа с LLM: fine-tuning, prompt engineering, повышение качества ответов. Требования: — Опыт работы Data Scientist от 2 лет. — Уверенный Python. — Практический опыт с ML/NLP стеком (PyTorch, TensorFlow, Hugging Face).

Location: San Francisco, CA; New York, NY; Washington, D.C. Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. ABOUT THE PUBLIC SECTOR TEAM - Sierra recently received FedRAMP High certification, enabling us to bring our industry-leading technology to partners in the US public sector. We’re now building our founding public sector team to redefine the relationship between the government and its citizenry. - Today, our agents already enable citizens to access social services, report fraud, and understand complex government systems. Simultaneously, they empower government officials to better hear the concerns and inquiries of their constituencies. - We are explicitly nonpartisan and committed to empowering public servants to leverage AI to advance their important missions. - In our journey, we are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and Family. These values are the foundation of our work, and we are committed to upholding them in everything we do. WHAT YOU’LL DO As an Agent Strategist, you own how Sierra’s AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer’s thorniest, highest-stakes problems into agents that measurably move their business. - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, evaluation, launch, and continuous iteration in production. Translate mission goals, policy requirements, and operational workflows into an agent that performs reliably in the real world. - Be a trusted strategic advisor to public sector leaders. Work shoulder-to-shoulder with agency executives and program leaders to define success, prioritize opportunities, and shape an AI strategy grounded in mission impact. - Partner with working teams day to day. Run working sessions with program, operations, technology, security, legal, and procurement stakeholders; resolve issues as they arise; and make the decisions that keep deployments moving toward launch. - Identify new ways to expand our impact. Understand our partners' most urgent needs and develop roadmaps for new use cases, including proactive outreach, multilingual access, and long-horizon agents that can support people across multi-step journeys. - Directly shape the product and our public sector strategy. Surface unmet needs from customer work, prototype new approaches, and partner with research, product, platform, and public sector leadership to influence Sierra's roadmap, market strategy, and repeatable solutions for government. EXAMPLE PROJECTS These are the kinds of projects that strategists on our public sector team have worked on recently: - Improve access to benefits and services. Launch an agent that helps residents understand eligibility, gather the right information, and navigate a complex application or recertification process across channels and languages. - Modernize constituent support. Design an agent that answers policy and program questions, provides case or application status, and routes sensitive or exceptional situations to the right public servant with full context. - Make critical reporting easier and safer. Build trusted conversational experiences for reporting fraud, safety concerns, or other high-stakes issues while meeting rigorous privacy, security, accessibility, and auditability requirements. - Enable proactive government services. Create a roadmap for outbound agents that remind people about deadlines, explain program changes, or help them complete important next steps before a benefit or service is interrupted. - Build repeatable public sector capabilities. Use a live agency deployment as a design partnership to shape new platform capabilities, evaluation standards, or implementation patterns that can serve institutions across federal, state, and local government. WHAT YOU’LL BRING - Ownership and delivery. A track record of leading multiple complex, high-visibility initiatives and driving cross-functional teams from an ambiguous starting point to measurable outcomes - for example as part of an early team, consultancy, or otherwise.. - Technical aptitude. Comfort engaging directly with technical concepts, including reading API documentation, understanding data models and system architecture, and following engineering and security tradeoffs in design discussions. - Commitment to public service. A passion for public sector work and a belief in the potential of institutions to improve outcomes for the people and communities they serve. - Communication. Clear, direct, and persuasive communication across executive, operational, policy, and technical audiences, with the ability to turn complexity into shared decisions. - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as policy, stakeholder, or implementation conditions change. 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. - Experience working in or with federal, state, or local government, including familiarity with procurement, security and compliance, accessibility, policy implementation, or systems integration. - You’ve been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed. - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: San Francisco, CA; New York, NY Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. ABOUT THE TECH, MEDIA & TELECOM TEAM - We work with some of the world's most influential and recognizable companies, from global telecommunications providers and leading media brands to technology platforms that power businesses worldwide. - We build agents for the moments that matter, helping our customers rise to the occasion when service disruptions, major product launches, or global events like the World Cup https://www.linkedin.com/posts/claybavor_at-sierra-we-are-very-proud-to-have-partnered-share-7491200202284945410-Bg79/?utm_source=share&utm_medium=member_desktop&rcm=ACoAABYjELMBZfjrg-wrv53M1tVXGe93FF3eTww drive millions of customer interactions. - We bring Sierra’s Horizon https://sierra.ai/product/horizon vision to TMT by building agents that transform the entire customer relationship: - Telecommunications: Turn one of the most frustrating customer experiences into one of the most personal, with agents that understand each subscriber, optimize their plan and savings, anticipate opportunities to add value, and earn their loyalty over time. - Media: Turn every subscription into an ongoing, personalized relationship, with agents that help each subscriber get the most from their experience through the right content, offer, plan, and support from their free trial through retention. - Technology: Bring the white-glove customer experience traditionally reserved for the largest enterprise accounts to every customer, helping them adopt the product, discover new ways to get value, expand their usage, and successfully renew. WHAT YOU'LL DO As an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai, you own how Sierra’s AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer’s thorniest, highest-stakes problems into agents that measurably move their business. - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it’s the best version of itself in the real world. You’ll have real ownership and autonomy over the outcome. - Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers’ executives, understand what success actually means to their business, and shape the AI strategy that gets them there. - Partner with the customer’s working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch. - Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next. EXAMPLE PROJECTS These are the kinds of projects strategists on our TMT team work on: - Scope and launch a subscription-retention agent for a telecommunications or media company, then tune it to save more at-risk customers while preserving trust and brand voice. - Launch a top-of-funnel sales agent for a telecommunications provider that qualifies prospects, recommends plans and devices, and converts interest into new subscriptions. - Build a new-subscriber onboarding agent that activates service, ports numbers, configures devices, and reduces early-life churn. - Create a proactive, long-running agent that detects service or account issues, reaches out across channels, and manages resolution before the customer contacts support. - Develop a media growth agent that drives content discovery, trial conversion, plan upgrades, and subscription renewal. - Partner with Product to develop capabilities for TMT-scale traffic, including low-latency voice, multilingual experiences, proactive communications, and resilient performance during major launches or service events. WHAT YOU’LL BRING - Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships. - Communication. Clear, direct, and persuasive across technical and non-technical audiences. - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast. - Technical aptitude. Comfortable engaging directly with technical concepts — reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion. - Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes. - Interest in telecommunications, media, and technology. Experience in telecom, streaming and digital media, enterprise or consumer technology, or subscription businesses — and familiarity with customer care, billing, identity, content, or technical support systems — is a strong plus. EVEN BETTER... - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts. - You’ve been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed. - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business. - Client-facing consulting, solutions, or strategy experience in a technically complex environment. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

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

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

Location: San Francisco, CA; New York, NY Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. ABOUT THE HEALTHCARE TEAM - Our healthcare agents already reach over 50% of U.S. families. We partner with leading health plans, providers, and healthcare platforms to deliver AI agents that handle some of the most sensitive and high stakes conversations in any industry. From helping members understand their benefits to resolving billing questions with empathy, our healthcare agents are transforming how patients and policyholders interact with the healthcare system. - Our healthcare customers include major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms. - Join us to transform the patient experience across the healthcare system—and help build technology that makes care more accessible, more human and more affordable for everyone. WHAT YOU’LL DO As an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai, you own how Sierra’s AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer’s thorniest, highest-stakes problems into agents that measurably move their business. - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it’s the best version of itself in the real world. You’ll have real ownership and autonomy over the outcome. - Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers’ executives, understand what success actually means to their business, and shape the AI strategy that gets them there. - Partner with the customer’s working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch. - Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next. EXAMPLE PROJECTS These are examples of projects our healthcare team has worked on: - Lead the project for building AI agents for major health insurance networks that handle detailed questions like “what’s my co-pay for a primary care visit?” and “how many physical therapy sessions do I have left?” - Ideate and create a roadmap for growing value for large healthcare payers and providers. - Create AI agents for multi-site primary and urgent care providers that manage appointments and answer common questions across 30+ clinics. - Build agents that replace lengthy paper intake forms with conversational experiences, boosting pre-visit intake conversion rates. - Develop AI agents for healthcare financial platforms that help patients understand billing, payment status, explanations of benefits, and financial assistance eligibility. WHAT YOU’LL BRING - Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships. - Communication. Clear, direct, and persuasive across technical and non-technical audiences. - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast. - Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion. - Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes. - Genuine interest in healthcare and improving patient/member experiences. Experience in healthcare technology, health IT or working with healthcare organizations and an understanding of healthcare compliance requirements (HIPAA, PHI handling and healthcare data privacy) are a strong plus. EVEN BETTER... - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts. - You’ve been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed. - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: Berlin Workplace: Hybrid OUR STORY: Every year millions of people are either filing their taxes in fear or giving up on their tax refund altogether. We're working on fixing that. Our intuitive app enables anyone, regardless of education or background, to file their taxes with newfound confidence. Spread across Germany, Spain and the UK, the team at Taxfix Group with its brands Taxfix and Steuerbot, is a compassionate group of solution-finders. We speak our minds openly, and with over 400 professionals, including tax experts, developers, and IT security experts, we're rich in ideas and voices. The group has facilitated more than 3.5 billion euros in tax refunds for its customers since its founding in 2016. THE OPPORTUNITY: As a (Senior) Software Engineer, you’ll build core features for our flagship product, turning complex tax scenarios into simple, reliable experiences. You’ll bring a builder-first mindset: staying close to customer problems, using AI and modern engineering tools to move from idea to impact quickly, and taking ownership of outcomes—not just code. You’ll work hands-on in a cross-functional team and bring deep expertise in either frontend or backend engineering, while collaborating effectively across the stack. You’ll help us raise the bar for scalable design, quality, maintainability, and AI-first software development. YOUR RESPONSIBILITIES AND DECISIONS: - Partner with product management, design, and engineering to understand customer problems, shape pragmatic solutions, and deliver measurable outcomes. - Own work end to end—from discovery and technical design through implementation, release, monitoring, and iteration. - Turn ambiguity into action, make sound trade-offs, and deliver valuable increments without compromising long-term maintainability. - Contribute to technical direction and strategy in support of the long-term product vision. - Use AI-assisted development tools in your daily engineering work to accelerate exploration, implementation, testing, debugging, and documentation while maintaining high engineering standards. - Critically evaluate, validate, and troubleshoot AI-generated output, using effective prompting and appropriate safeguards rather than accepting results at face value. - Share effective AI-assisted development practices, encourage responsible experimentation, and help teammates improve how they use AI tools. - Improve developer experience through tools, automation, and engineering practices that enable reliable, frequent delivery. - Collaborate across product and platform teams, and contribute to an environment where people learn, grow, give constructive feedback, and raise challenges safely. YOUR PROFILE: - Professional software engineering experience (React, Node.js) and designing reliable backend services and APIs. Experience with React Native experience is a plus. - Able to work effectively across system boundaries and collaborate with engineers outside your primary specialism. - Use AI-assisted development tools in your daily engineering work to accelerate exploration, implementation, testing, debugging, and documentation while maintaining high engineering standards. - Able to evaluate and troubleshoot AI-generated output, use effective prompting where relevant, and share practical learnings with teammates. - Experience working with a public cloud environment such as Google Cloud, AWS, or Microsoft Azure. - Familiarity with DevOps concepts and practices, including CI/CD, observability, and operating software in production. - Understanding of core application and backend concepts such as authentication, databases, distributed systems, cloud infrastructure, and API integrations. - A builder-first, pragmatic approach: You turn customer problems into shipped outcomes. You take initiative, test and learn quickly, and make clear trade-offs between speed, quality, maintainability, and risk. - Passion for writing maintainable, elegant code and continuously improving how software is built. - A collaborative, positive attitude and a willingness to challenge ideas constructively. - You have a builder mindset. You thrive in environments where things are still taking shape, take initiative to move ideas forward, and find ways to create impact even when the path isn't fully defined. - You embrace trying things out over waiting for perfect conditions, ship early to learn fast, and treat iteration as progress.   WHY TAXFIX? - A chance to do meaningful, people-centric work with an international team of passionate professionals. - Holistic well-being with free mental health coaching sessions and yoga. - A monthly allowance to spend on an extensive range of services that you can use and roll over as flexibly as you like. - Employee stock options for all employees—because everyone deserves to benefit from the success they help to create. - 30 annual vacation days and flexible working hours. - Work from abroad for up to six weeks every year. Just align with your team, and then enjoy your trip. - Plenty of opportunities to socialise as a team. In addition to internal tech meetups, our international team hosts regular get-togethers—virtually and in person when possible. - Free tax declaration filing, of course, through the Taxfix app—and internal support for all personal tax-related questions. - Have a four-legged friend in your life? We’re happy to have dogs join us in the office. Excited? So are we. Check out our Life at Taxfix page on LinkedIn to get a glimpse of our culture.   At Taxfix, we believe that incredible things happen when you have a wealth of perspectives and experiences. We're proudly committed to equal employment and development opportunities no matter your gender, race, religion, age, sexual orientation, colour, disability, or place of origin. To help mitigate any potential unconscious biases, we ask that you refrain from including your picture, age, or marital status on your CV. Let your experiences speak for themselves. Not sure if you meet all the requirements for this role? Please apply anyway. You might bring something special to the team that we hadn't considered previously.

Location: Madrid Workplace: Hybrid OUR STORY: Every year millions of people are either filing their taxes in fear or giving up on their tax refund altogether. We're working on fixing that. Our intuitive app enables anyone, regardless of education or background, to file their taxes with newfound confidence. Spread across Germany, Spain and the UK, the team at Taxfix Group with its brands Taxfix and Steuerbot, is a compassionate group of solution-finders. We speak our minds openly, and with over 400 professionals, including tax experts, developers, and IT security experts, we're rich in ideas and voices. The group has facilitated more than 3.5 billion euros in tax refunds for its customers since its founding in 2016. THE OPPORTUNITY: This role is based in Madrid, and requires at least 1 day a week in office presence as we work on a hybrid model. As a Senior Software Engineer, you’ll build core features for our flagship product, turning complex tax scenarios into simple, reliable experiences. You’ll bring a builder-first mindset: staying close to customer problems, using AI and modern engineering tools to move from idea to impact quickly, and taking ownership of outcomes—not just code. You’ll work hands-on in a cross-functional team and bring deep expertise in either frontend or backend engineering, while collaborating effectively across the stack. You’ll help us raise the bar for scalable design, quality, maintainability, and AI-first software development. YOUR RESPONSIBILITIES: - Partner with product management, design, and engineering to understand customer problems, shape pragmatic solutions, and deliver measurable outcomes. - Own work end to end—from discovery and technical design through implementation, release, monitoring, and iteration. - Turn ambiguity into action, make sound trade-offs, and deliver valuable increments without compromising long-term maintainability. - Contribute to technical direction and strategy in support of the long-term product vision. - Use AI-assisted development tools in your daily engineering work to accelerate exploration, implementation, testing, debugging, and documentation while maintaining high engineering standards. - Critically evaluate, validate, and troubleshoot AI-generated output, using effective prompting and appropriate safeguards rather than accepting results at face value. - Share effective AI-assisted development practices, encourage responsible experimentation, and help teammates improve how they use AI tools. - Improve developer experience through tools, automation, and engineering practices that enable reliable, frequent delivery. - Collaborate across product and platform teams, and contribute to an environment where people learn, grow, give constructive feedback, and raise challenges safely. YOUR PROFILE: - Professional software engineering experience (React, Node.js) and designing reliable backend services and APIs. Experience with React Native experience is a plus. - Able to work effectively across system boundaries and collaborate with engineers outside your primary specialism. - Use AI-assisted development tools in your daily engineering work to accelerate exploration, implementation, testing, debugging, and documentation while maintaining high engineering standards. - Able to evaluate and troubleshoot AI-generated output, use effective prompting where relevant, and share practical learnings with teammates. - Experience working with a public cloud environment such as Google Cloud, AWS, or Microsoft Azure. - Familiarity with DevOps concepts and practices, including CI/CD, observability, and operating software in production. - Understanding of core application and backend concepts such as authentication, databases, distributed systems, cloud infrastructure, and API integrations. - A builder-first, pragmatic approach: You turn customer problems into shipped outcomes. You take initiative, test and learn quickly, and make clear trade-offs between speed, quality, maintainability, and risk. - Passion for writing maintainable, elegant code and continuously improving how software is built. - A collaborative, positive attitude and a willingness to challenge ideas constructively. - You have a builder mindset. You thrive in environments where things are still taking shape, take initiative to move ideas forward, and find ways to create impact even when the path isn't fully defined. - You embrace trying things out over waiting for perfect conditions, ship early to learn fast, and treat iteration as progress. - You are able to be based in Madrid and work on a hybrid model ( 1 day per a week )   WHY TAXFIX? - A chance to do meaningful, people-centric work with an international team of passionate professionals. - Holistic well-being with free mental health coaching sessions and yoga. - A monthly allowance to spend on an extensive range of services that you can use and roll over as flexibly as you like. - Employee stock options for all employees—because everyone deserves to benefit from the success they help to create. - 30 annual vacation days and flexible working hours. - Work from abroad for up to six weeks every year. Just align with your team, and then enjoy your trip. - Plenty of opportunities to socialise as a team. In addition to internal tech meetups, our international team hosts regular get-togethers—virtually and in person when possible. - Free tax declaration filing, of course, through the Taxfix app—and internal support for all personal tax-related questions. - Have a four-legged friend in your life? We’re happy to have dogs join us in the office. Excited? So are we. Check out our Life at Taxfix page on LinkedIn to get a glimpse of our culture.   At Taxfix, we believe that incredible things happen when you have a wealth of perspectives and experiences. We're proudly committed to equal employment and development opportunities no matter your gender, race, religion, age, sexual orientation, colour, disability, or place of origin. To help mitigate any potential unconscious biases, we ask that you refrain from including your picture, age, or marital status on your CV. Let your experiences speak for themselves. Not sure if you meet all the requirements for this role? Please apply anyway. You might bring something special to the team that we hadn't considered previously.

Задачи: — Разработка и внедрение ML/NLP решений для реальных продуктовых задач. — Работа с LLM: fine-tuning, prompt engineering, повышение качества ответов. Требования: — Опыт работы Data Scientist от 2 лет. — Уверенный Python. — Практический опыт с ML/NLP стеком (PyTorch, TensorFlow, Hugging Face).

Задачи: — Руководить проектированием и развитием масштабируемых распределённых систем на Go — Отвечать за интеграцию и конфигурацию AI — от выбора моделей и интеграции API до prompt engineering и развертывания в продакшене — Переводить бизнес-цели в технические дорожные карты и планы поставки — Проводить архитектурные и код-ревью, наставлять старших инженеров — Представлять инженерную команду на встречах с внешними заинтересованными сторонами и оспаривать нереалистичные требования — Улучшать процессы CI/CD, наблюдаемости и инженерные процессы — Балансировать между кодированием, руководством командой и архитектурным контролем Требования: — 5–6+ лет коммерческого опыта с Go — 2+ года в роли технического лидера или ведущего инженера — Глубокие знания распределённых систем, микросервисов и конкурентности в Go (goroutines, каналы, синхронизация) — Практический опыт внедрения, настройки или интеграции AI/ML решений в продакшн-бэкендах, включая работу с LLM, RAG pipeline, OpenAI API, LangChain или аналогичными фреймворками — Опыт с CI/CD, облачной инфраструктурой и современными DevOps практиками — Высшее образование в IT — Готовность работать по CEST и использовать корпоративный ноутбук — Готовность выполнить live coding на Go во время интервью Условия: — Работа над долгосрочным продуктом с реальным бизнес-эффектом — Международная распределённая команда с коллаборативной культурой — Возможность взять ответственность за зрелое приложение — Гибкие условия работы и удалёнка

Задачи: — Развивать платформу: работать над функционалом, стабильностью и производительностью; — Развивать AI-функционал: LLM-based сценарии, tool calling, RAG, работу с контекстом, кэширование и другие механики; — Разбираться со сложными production-инцидентами и устранять причины проблем; — Превращать пожелания клиента в дорожную карту запуска; — Проектировать архитектуру интеграции Sance.AI с инфраструктурой клиента; — Отвечать за техническую часть сложных клиентских запусков от discovery до production; — Менторить junior/middle-разработчиков, помогать с декомпозицией задач, архитектурой и сложными техническими вопросами; — Проводить code review и повышать качество решений команды. Требования: — Опыт от 4 лет в разработке, желательно с production-опытом в AI/LLM-продуктах; — Уверенные знания Python и backend: asyncio, очереди, кеширование, конкурентность; — Практический опыт создания production-функционала на базе LLM, а не только использование ChatGPT; — Опыт с OpenAI API или другими LLM API, prompt engineering, tool calling, RAG, caching, context management; — Опыт с embeddings, vector search, agentic workflows, тестированием и evals; — Понимание production-проблем: latency, стоимость, rate limits, hallucinations, retries, observability; — Уверенная работа с REST API сторонних сервисов, webhooks и внешними сервисами; — Опыт интеграций с CRM, особенно amoCRM и/или Bitrix24; — Самостоятельность и ownership: умение довести размытую бизнес-задачу до работающего production-решения, видеть системные проблемы и помогать команде расти. Будет плюсом: — Опыт B2B/Enterprise-внедрений, highload и event-driven систем; — Собственные AI-проекты и опыт работы в стартапах. Условия: — Работа в быстрорастущем AI-стартапе, влияние на продукт, архитектуру и процессы; — Разнообразные задачи, крупные клиенты и короткий путь от идеи до production; — Быстрый карьерный рост.