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Location: London Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU’LL DO We’re hiring a Commercial Counsel to be a core member of Sierra’s legal team. We are looking for someone who has deep expertise in commercial contracts, but also someone who is eager to broaden their scope across IP, regulatory, and product. You will thrive in dynamic environments, enjoy tackling challenges beyond your comfort zone, and be excited to contribute across the business. In return, we’ll provide the support and opportunities you need to grow and excel as a lawyer. You’ll be part of a legal team that is highly respected within both the company and the broader legal industry—committed to excellence, collaboration, and making a meaningful impact. - Commercial Contracting: Structure, negotiate, and advise on all commercial contracts, including SaaS subscription agreements, technology licenses, professional services agreements, channel partner agreements, vendor agreements, and NDAs. Commercial privacy and security contracting experience (e.g., DPAs, BAAs, security agreements) is a plus. - Operational Excellence: Help build out our commercial function to be best-in-class. We aim to be the fastest and strongest, where the legal team is the differentiator in the contract lifecycle. You will be developing templates, playbooks, and workflows to drive efficiency and scalability. - Expertise: Deep knowledge of practice areas that underpin the commercial practice, including contract law, IP and privacy. You will also want to work in AI and understand the nuances of law as it relates to AI, including the evolving regulatory frameworks. You will be expected to advise broadly on all contractual issues and be comfortable doing so. - Teamwork: A team player first and foremost. Sierra is a unique place to work, with a strong sense of togetherness, and the legal team is no exception. You will look out for your colleagues and be accustomed to sharing and helping the team succeed. - Judgment: Understand risk in the context of a hyperscaling business, have sound judgment, and be strategic in your decision-making. You will not be afraid to make judgment calls, and you will be empowered to do so. - Approach: A strong work ethic with an eye for detail. You will strive for perfection and expect that of others. - Collaborate: Collaborate cross-functionally with Sales, Operations, and Agent Development teams to support revenue growth and strategic business initiatives. WHAT YOU’LL BRING - 2-6 years of legal experience, with a combination of both large law firm and in-house experience at a tech company. - A strong background in negotiating and managing complex commercial contracts, preferably in SaaS, AI, or enterprise software. - Strong communication skills (verbal and written) and the ability to partner with both legal and non-legal stakeholders. - A proactive mindset and the ability to navigate ambiguity in a fast-paced, dynamic startup environment. EVEN BETTER… - Experience of privacy/regulatory frameworks and can advise on data processing agreements and security-related contract provisions. - Non-English languages, especially Spanish, German and French. - A passion for AI, with a deep understanding of AI products, LLMs and the related legal issues. - Law firm experience at a top-tier, internationally recognized law firm. - Experience working at a high-growth startup and operating with a sense of ownership. - Industry specific knowledge in any of the following: Financial Services, Healthcare, Telecoms, Insurance and/or Consumer. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: San Francisco, CA Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU’LL DO We're hiring a Product Counsel to be a core member of Sierra's growing legal team. This role will report to our Associate General Counsel, Product and Privacy, as part of our growing product legal function. We are looking for someone who has deep expertise in product counseling for AI or other emerging technologies. You will be a legal partner for Sierra’s product and engineering teams, and help shape how our products go to market responsibly, ensuring privacy, compliance, and risk considerations are embedded throughout the product lifecycle. You will thrive in dynamic environments, enjoy tackling challenges beyond your comfort zone, and be excited to contribute across the business. In return, we'll provide the support and opportunities you need to grow and excel as a lawyer. You'll be part of a legal team that is highly respected within the company — committed to excellence, collaboration, and making a meaningful impact. Product - End-to-end responsibility for product legal support: counsel Product and Engineering teams from concept through launch across Sierra's agent platform and new products. - Work closely with Engineering teams to integrate compliance and privacy-by-design principles and AI transparency measures into product development. - Advise the customer-facing Agent Development teams on legal requirements of product features, including consumer protection, telecommunications (e.g., voice and messaging), and industry-specific requirements for regulated customers. - Develop scalable product review processes, launch checklists, and self-serve guidance that let product teams move quickly. Regulatory (with focus on AI) - Advise on emerging AI-specific regulations and their applicability to Sierra's products. - Partner with the privacy team to implement AI governance policies and frameworks to ensure responsible AI deployment. - Monitor legal developments affecting AI products, advising product leadership on risks, trends, and design implications. WHAT YOU’LL BRING - 4+ years of legal experience, with a combination of large international law firm and in-house experience at a tech company. - Experience advising product and engineering teams on new product development, ideally involving AI/ML, communications, or platform products. - Working knowledge of the legal domains that touch product development, including privacy (e.g., GDPR, CCPA), AI regulatory frameworks (e.g., EU AI Act, NIST AI Risk Management Framework), consumer protection, and IP. - Ability to partner with technical teams to understand all aspects of Sierra's product offering. - Strong analytical skills and the ability to balance legal risks and business objectives in a fast-moving environment. - Strong verbal and written communication skills and the ability to partner with both legal and non-legal stakeholders. - A strong work ethic with an eye for detail. You will strive for perfection, and expect that of others. - Be a team player first and foremost. Sierra is a unique place to work, with a strong sense of togetherness, and the legal team is no exception. You will look out for your colleagues, be accustomed to sharing and helping the team succeed. EVEN BETTER… - Experience with voice/telephony products and related regulatory regimes (e.g., TCPA, state call recording laws). - Experience counseling on products sold into regulated industries (healthcare, financial services). - Familiarity with machine learning models and their associated risks. - Previous experience developing trust and safety or responsible AI programs. - Startup experience and comfort with rapid iteration and ambiguity. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: San Francisco, CA Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU’LL DO We’re hiring a Senior Commercial Counsel to be a core member of Sierra’s legal team. We are looking for someone who has deep expertise in commercial contracts, but also someone who is also eager to broaden their scope across IP, regulatory, and product. You will thrive in dynamic environments, enjoy tackling challenges beyond your comfort zone, and be excited to contribute across the business. In return, we’ll provide the support and opportunities you need to grow and excel as a lawyer. You’ll be part of a legal team that is highly respected within both the company and the broader legal industry—committed to excellence, collaboration, and making a meaningful impact. - Commercial Contracting: Structure, negotiate and advise on all commercial contracts, including SaaS subscription agreements, technology licenses, professional services agreements, channel partner agreement, vendor agreements and NDAs. Commercial privacy and security contracting experience (e.g., DPAs, BAAs, security agreements) is a plus. - Operational Excellence: Help build out our commercial function to be best in class. We aim to be the fastest and strongest, where the legal team is the differentiator in the contract lifecycle. You will be developing templates, playbooks, and workflows to drive efficiency and scalability. - Expertise: Deep knowledge of practice areas that underpin the commercial practice, including contract law, IP and privacy. You will also want to work in AI and understand the nuances of law as it relates to AI, including the evolving regulatory frameworks. You will be expected to advise broadly on all contractual issues and be comfortable doing so. - Teamwork: A team player first and foremost. Sierra is a unique place to work, with a strong sense of togetherness, and the legal team is no exception. You will look out for your colleagues, be accustomed to sharing and helping the team succeed. As the team grows, you will train and mentor more junior members. - Judgement: Understand risk in the context of a hyper-scaling business, have sound judgement and be strategic in your decision making. You will not be afraid to make judgement calls, and you will be empowered to do so. - Approach: A strong work ethic with an eye for detail. You will strive for perfection, and expect that of others. - Collaborate: Collaborate cross-functionally with Sales, Operations, and Agent Development teams to support revenue growth and strategic business initiatives. WHAT YOU’LL BRING - 6+ years of legal experience, with a combination of both large law firm and in-house experience at a tech company. While we are looking for a Senior Legal Counsel, we are open to considering exceptional candidates with less experience as Commercial Counsel. - A strong background in negotiating and managing complex commercial contracts, preferably in SaaS, AI, or enterprise software. - Strong communication skills and the ability to partner with both legal and non-legal stakeholders. - A proactive mindset and the ability to navigate ambiguity in a fast-paced, dynamic startup environment. EVEN BETTER… - Experience of privacy/regulatory frameworks and can advise on data processing agreements and security-related contract provisions. - A passion for AI, with a deep understanding of AI products, LLMs and the related legal issues. - Significant law firm experience at a top-tier, internationally recognized law firm. - Experience working at a high-growth startup and operating with a sense of ownership. - Industry specific knowledge in any of the following: Financial Services, Healthcare, Telecoms, Insurance and/or Consumer. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: San Francisco, CA Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. ABOUT THE ROLE Sierra is hiring an Digital Marketing & Campaigns Lead to build and lead the function that turns our business priorities into measurable, integrated marketing programs. You will own the global campaign portfolio across digital and offline channels and account-based programs, with responsibility for creating pipeline, accelerating priority opportunities, and supporting expansion within existing customers. This is a builder role for a leader who’s excited to roll up their sleeves, set global strategy, establish a scalable operating model, develop a strong team, and maintain a high bar for craft and execution. You will partner closely with Sales, Marketing Operations, Product Marketing, Brand, Events, Communications, and regional Marketing leaders. What You'll Do: - Drive our campaign strategy: Build an integrated, full-funnel campaign portfolio spanning paid media, organic search, web, email, content, social, OOH, print, and account-based programs. Give every program a clear audience, message, channel role, and business objective. - Turn business priorities into pipeline: Translate company priorities by account, vertical, buyer, and region into programs that support acquisition, deal acceleration, and customer expansion. Balance always-on programs with launches and high-impact market moments. - Build Sierra’s named-account motion: Orchestrate always-on account-based marketing for Sierra’s highest-priority accounts. - Own investment and performance: Set pipeline targets, manage budgets, and determine the right channel and program mix. Partner with our operations team on attribution, forecasting, reporting, and lead flow. Use performance data to scale what works, stop what does not, and reallocate investment quickly. - Set the standard for execution: Establish clear campaign planning, briefing, quality assurance, launch, and optimization rhythms. Inspect high-impact work personally and ensure Sales has the messaging, assets, and follow-up needed to convert engagement into opportunities. - Build and lead the team: Hire, coach, and develop a high-performing team of digital marketing and campaigns professionals. Establish clear ownership, strong operating rhythms, and a culture of accountability, experimentation, and continuous improvement. - Use AI to multiply impact: Embed AI and automation across research, audience development, content adaptation, experimentation, and reporting. Increase the team’s speed and reach while maintaining human judgment, accuracy, and brand quality. WHO YOU’LL WORK WITH You’ll partner closely with Sales, Operations and Agent Development to turn account, vertical, and regional priorities into measurable programs and shared goals — as well as the entire Marketing team to drive awareness, credibility and pipeline. You’ll also partner with Finance on investment planning and with executive leaders on priorities, performance, and tradeoffs. Together, these teams will create a coordinated buyer journey from first engagement through opportunity progression and customer expansion. WHAT YOU'LL BRING: - 12+ years of digital marketing, integrated campaigns, or demand generation experience. - A proven record of building and leading teams responsible for pipeline targets, substantial marketing investments, and global campaign portfolios. - Deep experience with complex, sales-led enterprise motions, including named accounts, long sales cycles, multi-stakeholder buying committees, and both new-logo and expansion programs. - Experience creating global strategies that allow for meaningful regional and market-level adaptation. - Strong data fluency, including attribution, forecasting, experimentation, funnel analysis, and translating performance into clear investment recommendations. - The ability to move between executive-level strategy and detailed campaign decisions without losing speed or quality. - Strong cross-functional leadership and executive communication skills, especially across Sales, Operations, Finance, and Marketing. - Practical fluency with AI-powered marketing tools and sound judgment about where automation improves performance and where human expertise remains essential. EVEN BETTER... - Experience building an integrated marketing function at a fast growing enterprise SaaS or AI company. - A track record of creating industry specific campaigns that engage senior executives and drive measurable pipeline within priority accounts. - Experience expanding marketing programs internationally, with a strong understanding of how buyer needs, messaging, and channels vary across markets. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: Singapore Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU'LL DO - Lead & develop a high-performing sales team - Hire, onboard, and develop Enterprise/Strategic AEs covering Southeast Asia. Coach reps on deal strategy, pipeline management, and execution. Create a culture of accountability, learning, and collaboration. Identify and grow future leaders on your team. - Own regional performance - Own your regional number and forecast accuracy, Inspect pipeline quality and help unblock stalled deals. Drive consistent execution of our sales process. Partner with RevOps to ensure clean data and clear insights. - Be deeply involved in deals - Join key customer and prospect conversations. Help reps navigate complex buying committees and late-stage deals. Support pricing, negotiation, and close strategy. WHAT YOU'LL BRING - 10- 15+ years of experience in an Enterprise customer-facing sales role, identifying and closing large accounts. - People Leadership Experience: 5+ years managing, mentoring, and developing a high performing enterprise sales team. - Enterprise Experience: Experience managing a $1M+ quota, and running end-to-end complex deals. - Strong Communication Skills: Exceptional verbal and written communication abilities. - Analytical Mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions. EVEN BETTER... - Industry Knowledge: Familiarity with the AI landscape, key players, and emerging trends. - Experience Building GTM Strategies: Building sales teams and sales motions from scratch, or from early stage growth. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - 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. This role is open to MBA students graduating in spring 2027. WHAT YOU’LL DO As an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai, you own how Sierra’s AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer’s thorniest, highest-stakes problems into agents that measurably move their business. - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it’s the best version of itself in the real world. You’ll have real ownership and autonomy over the outcome. - Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers’ executives, understand what success actually means to their business, and shape the AI strategy that gets them there. - Partner with the customer’s working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch. - Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next. EXAMPLE PROJECTS These are the kinds of projects that strategists on our team have worked on recently: - Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers. - Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation. - Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services for examples. - Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner. - Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome https://sierra.ai/blog/outcome-based-pricing-for-ai-agents week over week. WHAT YOU’LL BRING - Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships. - Communication. Clear, direct, and persuasive across technical and non-technical audiences. - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast. - Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion. - Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes. EVEN BETTER... - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts. - You’ve been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed. - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or experience at the intersection of technology and business. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: London Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU’LL DO As a Partnerships Development Lead, you’ll play a critical role in building and nurturing a robust ecosystem of partners and stakeholders around Sierra, amplifying our reach and market impact. - Industry Partnerships: Develop and grow partnerships with key industry players and technology platforms - Strategic Customer Channels: Explore and cultivate alternative customer acquisition channels beyond traditional sales, leveraging Sierra’s ecosystem of investors, partners, and industry influencers to drive inbound interest and adoption - GTM Strategy & Collaboration: Align partnership efforts with Sierra’s broader GTM approach, collaborating closely with Sales and Marketing - Investor & VC/PE Engagement: Build and deepen relationships with VCs and PE firms to position Sierra as a strategic AI partner across their portfolios. Proactively identify opportunities to introduce Sierra to portfolio companies that would benefit from our agents - Industry & Market Expansion: Gather market intelligence, share insights to inform product development, and explore opportunities for potential growth across new market segments and geographies WHAT YOU’LL BRING - 8+ years in business development, strategic partnerships, or related roles in tech - Strong understanding of the VC/PE landscape and experience working with investors - Proven track record of structuring and closing high-value partnerships with senior stakeholders - Ability to engage and maintain relationships with C-level executives, investors, and key decision-makers - Analytical mindset to evaluate partnership opportunities and align them with Sierra’s long-term vision - Ability to navigate ambiguity in a fast-moving startup environment EVEN BETTER… - Prior experience at a high-growth AI or enterprise SaaS startup - Deep expertise in a few of our key industries: financial services, healthcare, telecommunications, media, travel, transportation and hospitality, retain and consumer goods, and/or technology - Experience structuring and managing ecosystem partnerships 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; Toronto Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU’LL DO - 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 - Language fluency - professional fluency in both Spanish and English - Experience building and scaling end-to-end production systems - Strong technical problem-solving skills, especially in fast-changing, ambiguous environments - A builder and tinkerer’s mindset with high agency - you find creative ways to overcome obstacles and ship - Comfort working directly with customers to understand their needs and solve real-world problems - Excellent communication skills - clear, direct, and persuasive across technical and non-technical audiences EVEN BETTER... - Experience building or deploying AI/LLM systems in production - Have been a founder or founding engineer - you know what it means to balance craft, ownership, and speed - Familiarity with tools that power today's AI agents: eval frameworks, agent tooling, RAG pipelines, and prompt engineering - Prior experience with React, TypeScript, and/or Go - Previous roles where you interfaced with customers or led technical projects with external stakeholders OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: European Union About Toloka 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 ove r 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 and Nebius Group 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. About the Team We are the ML team inside Toloka — we build the machine-learning products that power the platform itself, so every project running on Toloka is faster, cheaper, and more reliable. A few examples of what we own: Enterprise post-training- we are helping real companies by providing them small LLMs that beat frontier models in quality at a fraction of the cost. Off-the-shelf post-training - we are conducting research on datasets we deliver to clients, showing that training on these datasets will improve their performance. Fine-tuning and RL — adapting frontier and open-source models to Toloka's tasks to hit the right quality at the right cost. Evaluation, benchmarking, cost modeling, and model selection across providers. LLM QA — the core technology behind Toloka's automated quality-check mechanism. Every annotation flowing through Self-Service is reviewed by an LLM agent we design, train, and operate. We own the full chain. The same team designs the ML solution, ships it to production, keeps it running 24/7, analyzes the results coming back from real projects, and feeds that signal into the next iteration. No hand-off between research, engineering, and operations — it's all us. About the Position As a Principal ML Researcher, you will define the overarching technical vision, research strategy, and architecture for Toloka’s core ML and post-training stack. In this high-impact role, you will bridge frontier AI research and large-scale platform engineering. You will lead technical strategy across greenfield post-training paradigms (such as GRPO, process/outcome reward modeling, and RLAIF), architect resilient automated evaluation ecosystems, and set the standard for how foundation models are adapted and served on our platform. As a technical authority, you will mentor senior ML engineers, collaborate directly with executive leadership, and represent Toloka in the broader AI research community. What you’ll do Drive Technical Strategy: Define the multi-quarter strategy and architecture for Toloka’s post-training stack, ensuring our fine-tuning, RL, and evaluation capabilities stay ahead of industry trends. Architect Greenfield Post-Training & RL Pipelines: Spearhead the transition beyond basic SFT into advanced RL frameworks (GRPO, PPO/DPO, reward modeling, Process Reward Models, and RLAIF) to power platform-wide LLM alignment and agent behavior. Pioneer Next-Gen Evaluation Harnesses: Design and calibrate bulletproof automated evaluation ecosystems, including human-aligned LLM-as-a-judge frameworks, dynamic benchmarking suites, and regression control setups. Advance Distillation & Inference Optimization: Lead research initiatives on model distillation, quantization, context compression (e.g., gisting), and speculative decoding to optimize latency-cost trade-offs at platform scale. Shape Agentic Platform Capabilities: Architect autonomous guiding agents and tool-use workflows, establishing foundational frameworks for multi-step reasoning, self-correction, and evaluation-driven feedback loops. Technical Leadership & Mentorship: Elevate the engineering and research bar across the team through architectural design reviews, hands-on mentoring of Senior ML Researchers, and establishing best practices for reproducible ML R&D. Cross-Functional & Community Influence: Partner with Product and Engineering directors to translate complex client challenges into scalable platform architecture; author high-impact research write-ups, blog posts, and external tech talks. What we're looking for 6+ years in ML engineering or applied research, with 3+ years of proven track record leading LLM post-training, fine-tuning, or alignment initiatives at scale. Deep theoretical and practical mastery of LLM alignment: SFT, LoRA/PEFT, RLHF/RLAIF (GRPO, DPO, PPO), reward modeling, and reasoning-oriented post-training. Mastery of LLM Evaluation & Calibration: Proven history of building evaluation pipelines from scratch, addressing LLM-as-a-judge biases, and tightly calibrating automated evals against human gold standards. Expert Distributed Training & Systems Engineering: Strong proficiency in Python, PyTorch, distributed training frameworks (Deepspeed, Megatron, FSDP), and high-performance inference engines (vLLM, TensorRT-LLM). Architectural Vision & Product Leadership: Demonstrated ability to map ambiguous technical challenges into robust platform features, balancing state-of-the-art research with production reliability and cost constraints. Technical Authority: Proven experience acting as a technical leader, mentoring senior researchers/engineers, and influencing cross-functional roadmaps. Language: Fluent spoken and written English (C1), with clear communication skills to articulate complex technical concepts to both internal teams and external clients/community. What we can offer You will be part of an international, dynamic environment that drives innovation and sets new standards in the AI and technology sector. Competitive compensation package including base salary, bonus, and ESOP. Paid PTO and benefits will vary depending on location. We offer a full remote or hybrid model (if you are based in NL or Serbia). IT setup and home office allowances. Equal Opportunity Employer: Toloka is committed to providing equal opportunity and fostering an inclusive environment. We welcome applications from all qualified individuals and do not discriminate on the basis of race, religion, color, national origin, sex, sexual orientation, gender identity, age, marital status, veteran status, disability, or any other characteristic protected by applicable law. Selection decisions are made based on qualifications, merit, and business need. [Important Notice] Scam Alert Regarding Fake Job Postings It has come to our attention that an individual or group is fraudulently impersonating Toloka to post fake jobs and solicit personal information from applicants. Please be aware: Official Communication: Our recruiting team will only contact you from an official " toloka.ai " email address. We will NEVER use Gmail, Yahoo, Tolokainc, toloka.inc, or other personal or seemingly business email accounts. Our Process: We will never ask for your bank account details, credit card number, or any fees as part of the application or interview process. Official Listings: All legitimate job openings are posted on our official careers page: https://toloka.ai/careers#job-list What to do: If you see a suspicious job posting or have been contacted by someone you suspect is a scammer, please do not provide any personal information. Instead, report the incident to us directly at security@toloka.ai and report the profile/post to LinkedIn.We are taking this matter very seriously and are working with the appropriate parties to resolve it. Thank you for your vigilance! To learn how we collect, use, disclose, and store personal data, check out our Privacy Notice .

Location: San Francisco, CA Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU’LL DO You'll own the operational backbone that connects what we sell to what we bill: turning executed contracts and agent usage into accurate bookings and reports, and turning the data behind both into critical insights the business acts on. This role sits at the center of the company’s business model and works across Sales, Finance, Legal, Pricing, GTM Systems, and Agent Development. Own order management across the customer lifecycle - Own the path from signature to booking: build, verify, and book quotes across the customer lifecycle, capturing all critical commercial terms - Collaborate across GTM Operations, Finance, and Sales Compensation to ensure bookings flow accurately into all downstream systems and reporting - Leverage and spearhead order management guides and best practices, influencing policies and processes as new terms and products emerge Accelerate usage tracking and reporting - Partner with Agent Development to set up, verify, and maintain outcome-based usage tracking across agents - Run the monthly consumption reporting and billing cycle for our growing customer base, delivering key reports to the company and to the Customer - Serve as the owner for usage questions from customers, Sales, and Agent Development Support our deal operations and velocity - Draft, review, and execute order forms, working with our Pricing team to align on commercial negotiation, deal forecast, and downstream operability - Partner with Sales, Legal, Pricing, and Finance across the deal lifecycle to execute deals cleanly and drive scalability over time Build the operational machine with us - Continuously identify repetitive processes across the order management lifecycle and collaborate across the Go-to-Market Operations team to automate and scale them - Work with Revenue Operations and GTM systems to define billing processes and policies for new products and pricing models - Ramp from running standard processes to owning complex and ambiguous scenarios WHAT YOU’LL BRING - 2–4 years in deal desk, order management, billing operations, or revenue operations at a B2B SaaS company - Experience owning an operational booking and/or billing queue end-to-end with high accuracy against monthly deadlines - Experience with CRMs (e.g., Salesforce) and a CPQ or billing system; comfortable reading a contract and translating terms into system fields - Strong attention to detail and clear written communication skills to collaborate with Sales, Finance, Legal, and customers - Ability to identify areas for improvement and build solutions using AI tooling - Based in San Francisco and able to work in-office with the team EVEN BETTER… - Experience with usage-based billing (commitments, overages, credits, true-ups) - Familiarity with Quoting and Contract Lifecycle Management tools - SQL or spreadsheet modeling skills - Exposure to sales compensation, revenue recognition, or partner and reseller billing - Experience at a high-growth company where you helped stand up a process from scratch OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: San Francisco, CA 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. Sierra’s Applied Research team advances the quality, speed, and cost efficiency of the models powering our agents across a wide range of tasks. Our work spans post-training open-weight models for specialized capabilities and pioneering new approaches to voice AI, turning research breakthroughs into reliable production systems. WHAT YOU’LL DO - Tackle unsolved applied AI and ML problems. Pushing the boundaries of post-training, voice AI, and long-horizon task execution, building agents that can reason, adapt, and reliably carry out complex tasks for customers. - Determine when to build specialized models and when to use externally provided frontier intelligence, balancing quality, speed, and cost to deliver customer value. - Turn ambiguous product and customer problems into well-framed machine learning problems. - Develop, fine-tune, evaluate, and deploy models that improve Sierra’s customer-facing AI agents. - Advance our post-training work, from supervised fine-tuning toward reinforcement learning and long-horizon optimization. - Build rigorous evaluations that connect model performance to real-world agent quality. - Work with large-scale, proprietary datasets spanning text and audio interactions. - Collaborate across Sierra while taking ideas from experimentation through production deployment and customer impact. WHAT YOU’LL BRING - Strong experience building and deploying production machine learning and AI systems. We welcome backgrounds across applied ML, including search, ranking, recommendations, advertising, language, and speech. - Excellent judgment in framing product problems as ML tasks and selecting the simplest & most effective approach. - Experience working deeply with data, experimentation, evaluation, and model iteration. - A practical, evidence-driven approach to ML, with strong judgement around when a problem calls for modeling and when a simpler solution will deliver the best outcome. - The ability to operate with high agency and work across the stack when needed to deliver an outcome. - Alignment with Sierra’s values, including Craftsmanship, Customer Obsession, and Competitive Intensity. - A degree in computer science, machine learning, or a related field, or equivalent professional experience. EVEN BETTER… - Experience with supervised fine-tuning or reinforcement learning. - Experience in search, ranking, recommendations, or advertising systems. - Experience training and deploying language, speech, or multimodal models. - Experience designing model evaluations tied to real-world product outcomes. - Experience working with large-scale consumer datasets or high-volume ML products. - Contributions to applied ML research or benchmarks. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: San Francisco, CA Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. ABOUT THE ROLE Sierra’s AI agents depend on foundation models to reason and act in real time. The Inference team builds the systems that make those models fast, reliable, and efficient at scale. As a Software Engineer on Inference, you’ll help define Sierra’s inference architecture across both self-hosted models and third-party inference providers. You’ll work on the systems responsible for serving and routing inference, managing capacity and quota, and optimizing for latency, reliability, and cost. This is a systems-first role at the intersection of distributed infrastructure and AI. You don’t need to be an ML researcher—we’re looking for engineers who love complex systems problems and are excited to apply that expertise to one of the fastest-moving areas of AI infrastructure. WHAT YOU'LL DO - Partner with frontier labs and providers. At our scale, we rely on frontier labs, and inference providers to supply capacity, training and inference infrastructure. - Shape Sierra’s inference architecture. Design how inference traffic flows across models, infrastructure, and providers, including new serving and proxy layers as Sierra scales. - Build for low latency and high reliability. Develop systems for routing, failover, capacity management, and quota that keep inference performant and available across large-scale production workloads. - Build and operate self-hosted inference. Run models on GPU infrastructure, from building containers and operating inference engines to managing the underlying compute capacity. - Optimize inference performance. Work with the Applied Research team on techniques such as speculative decoding and serving-engine optimizations that improve latency, throughput, and cost. - Build across a hybrid inference stack. Work with both Sierra-managed infrastructure and leading inference platforms, making architectural decisions about where and how workloads should run. - Push the serving stack forward. Work closely with inference providers to tune engines and infrastructure for Sierra’s workloads. - Support the broader model lifecycle. Contribute to infrastructure that enables post-training while partnering closely with our Models and Agent Runtime teams. WHAT YOU'LL BRING - Deep systems thinking and strong distributed systems fundamentals. - Experience designing, building, and operating large-scale production systems. - Strong judgment around tradeoffs involving latency, reliability, capacity, and cost. - Experience taking ownership of complex infrastructure from architecture through production operation. - Excitement about applying systems expertise to AI infrastructure and learning quickly as the underlying technology evolves. EVEN BETTER - Experience with ML infrastructure, MLOps, or production inference systems. - Experience serving LLMs or other large models at scale. - Experience operating self-hosted inference and GPU infrastructure. - Familiarity with inference frameworks such as vLLM or SGLang. - Experience with post-training infrastructure or inference-performance optimization. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: London About us The Financial Times is one of the world’s leading news organisations, globally recognised for its authority, integrity and accuracy, with a mission to deliver quality information and services worldwide. At the FT, curiosity thrives and ambitious thinking is rewarded. Here, you’re given the chance to reach millions, create work that matters and deliver impartial journalism in a polarised world. In our warm, collaborative culture, you’ll connect with a diverse community of experts who support your growth, career aspirations and wellbeing. Your future at the FT will be filled with opportunities that challenge and inspire you. With no fixed path, you’ll discover new skills and forge a career that can take you anywhere. Build a newsworthy career at the FT. Our commitment to diversity, equity and inclusion We believe in the power of unique perspectives and want all voices in our organisation to be heard, respected and valued. A supportive workplace is one where employees feel they can be themselves and operate to their full potential. We are committed to removing barriers for everyone, with a focus on addressing those faced by underrepresented groups. The role Corporate development is a central part of the Financial Times Group’s growth strategy. Corporate Development & Investments (“CD&I”) is a small but high profile function reporting jointly to the FT CFO and the Honorary Chairman of the FT and Special Executive Adviser to Nikkei. The team is responsible for M&A (FT Group and Nikkei outside of Japan), FT Ventures (FT's Corporate Venture arm) and associated Strategic Partnerships, FT Portfolio Management, and internal investments assessments. We are looking for a Corporate Development & Investments Manager who is an innovative, creative, analytical and strategic thinker who can demonstrate passion about the future of our businesses. The ideal candidate enjoys solving problems and working alongside others, can take direction but is also proactive and is willing and able to work under their own initiative. It is essential that the candidate is a team player, is able to build strong professional relationships and has excellent communication skills. The role will involve significant exposure to the FT’s and Nikkei’s leadership team and various functions throughout the FT and Nikkei Group, and so an ability to establish credibility in working with senior management is essential. Key responsibilities The Manager will be supporting the Corporate Development & Investments team with: Sourcing corporate development opportunities - including acquisition and investment target sourcing; End-to-end contribution to M&A, FT Ventures investments and disposals - including business valuation modelling, business plan analysis and pricing, due diligence and transaction coordination, and contract negotiation; Leading the financial and valuation analysis of business opportunities and, applying critical thinking to the business case and how it progresses the FT and Nikkei’s strategies; Leading portfolio review projects and reviewing investment proposals; Leading thematic research projects and portfolio management; Mentoring more junior team members; and Preparation of board papers and any documentation required for CFO, CEO, FT Board and Nikkei approval processes. Required skills and experience The ideal candidate will have strong core technical skills acquired during active participation in M&A transactions, particularly with respect to financial modelling; Candidates will have at least 8 years relevant experience gained working in an investment bank or M&A advisory firm, the corporate finance division of a large accounting firm, a private equity or venture capital investor or within the M&A/ Corporate Finance/ Corporate Development function of a corporate organisation; Buy-side experience is essential; Strong undergraduate degree, ideally in economics, business, finance, law or accounting; Highly numerate and confident and experienced in financial modelling, valuation analysis and business plan and commercial analysis; Proven analytical and business and problem solving skills, with the ability to apply financial analysis to commercial issues; Excellent attention to detail, commitment to the job and a strong results-driven work ethic; Strong strategic acumen, and understanding of FT and Nikkei and the industries within which they operate; Demonstrable end to end transaction experience; Excellent English oral and written communication skills; Confident working under own initiative as well as ability to collaborate well and work with others; Ability to balance taking initiative with strong communication and collaboration across the team; Proficient in Microsoft Word, Excel and PowerPoint and Google Suite; as well as use of AI tools. Desirable Venture investing experience Strategy experience APAC M&A experience and network What's in it for You? Our benefits vary by location but we are committed to providing best-in-class perks across all our offices. These include generous annual leave, medical cover, inclusive parental leave packages, subsidised gym memberships and opportunities to give back to the community. Full details of our benefits are available here. We currently operate a hybrid model which requires staff to work onsite 50% of the time, subject to role requirements & regular review. While flexible working requests will be considered, not all patterns are suitable for all roles. We believe this balanced approach supports flexibility and protects our culture, making collaboration and communication easier, building stronger relationships and team cohesion, and supporting peer learning. We reserve discretion on reasonable notice to change this approach either generally or for specific individuals or teams. Accessibility We are a disability confident employer and Valuable 500 signatory. Please let us know if you require any reasonable adjustments/personalisation as part of the application process or to enable you to attend an interview. If you would like to discuss your requirements or have any questions, email talent@ft.com and a member of our team will be happy to help. Further information At the FT, we embrace innovation and the use of technology and appreciate that individuals may leverage AI tools as part of their job application process. Whilst we are happy for you to use AI to assist with your application, it is essential that all information provided is authentic and accurately represents your skills, experience, and qualifications. Candidates should be aware that the use of AI throughout the application process may be monitored to ensure a fair and transparent hiring process for all. Please beware of fraudulent job postings and offers claiming to be from the Financial Times. All legitimate opportunities will direct you to apply through the official Financial Times careers site, and the FT will never ask for financial information, payments, or referrals to third parties during the hiring process. If you have any concerns about the legitimacy of a job posting or suspect any scam activity, please contact talent@ft.com . Please answer the application questions below.

Location: New York, NY / Los Angeles, CA, 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 based in New York City or San Francisco to join Delivery team and help build, drive, and maintain solutions for our clients. 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 On-site role based in either San Francisco or New York City ( 40 hours per week ), with periodic travel across the city and surrounding areas to meet with clients. All business travel expenses are covered by the company; Personal and career development: we support employee’s ambition for professional development and encourage them to implement their ideas in their projects; Flexibility: we offer remote or hybrid employment. You will also design with your manager a workday that works best for you; Paid parental leave and sick leave; Medical insurance fully covered for the employee; 25 vacation days per year [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: Singapore Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU'LL DO As an Agent Strategist https://sierra.ai/blog/agent-strategist-your-phd-in-applied-ai, you own how Sierra's AI agents come to life for our customers — from first pilot to a production agent handling thousands of conversations a day. You sit at the intersection of product, building agents and customer-facing work, and stay just as close to the technology as you are to the people you build for. You transform a customer's thorniest, highest-stakes problems into agents that measurably move their business. - Own the Agent Development Life Cycle https://sierra.ai/blog/agent-development-life-cycle. Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production — translating business goals into an agent that outperforms, and tuning relentlessly until it's the best version of itself in the real world. You'll have real ownership and autonomy over the outcome. - Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and shape the AI strategy that gets them there. - Partner with the customer's working teams day to day. Run working sessions, troubleshoot the agent as issues come up, and make the calls that keep the build on track for launch. - Directly impact product. Surface unmet needs from your customer work, and feed them back to research and platform to shape where Sierra goes next. EXAMPLE PROJECTS These are the kinds of projects that strategists on our team have worked on recently: - Scope and launch a subscription-retention agent for a large telecommunications or media company that consistently outperforms human agents at saving at-risk customers. - Stand up an agent for a commerce customer that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation. - Redesign the conversation flows for a financial services agent so it can handle complex, regulated interactions — and convert a pilot into a multi-team production deployment. See our financial services blog https://sierra.ai/blog/five-ways-to-use-ai-agents-financial-services for examples. - Partner with product on a net-new capability — a new agent architecture or self-service tooling — using a live customer as the design partner. - Define the evaluation and quality bar for a new agent, then use those metrics to drive a measurable lift in outcome https://sierra.ai/blog/outcome-based-pricing-for-ai-agents week over week. WHAT YOU'LL BRING - Customer obsession. Genuine energy being in front of customers — understanding their business and needs, thriving in complex organizations, and building trusted relationships. - Communication. Clear, direct, and persuasive across technical and non-technical audiences. - Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt as things change fast. - Technical aptitude. Comfortable engaging directly with technical concepts - reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion. - Ownership and delivery. A track record of running multiple complex, high-visibility projects at once and driving them to outcomes. EVEN BETTER... - Experience building or deploying AI/LLM agents in production — hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering) — working closely with technical counterparts. - You've been a founder, founding team member, or operator — you know how to balance craft, ownership, and speed. - A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience — and/or an MBA or comparable experience at the intersection of technology and business. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

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

Location: United States About Toloka 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 ove r 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 and Nebius Group 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. Role Description We are seeking an exceptional Program Director to own and scale the execution of Enterprise fine-tuning projects across a major client portfolio. This role focuses on operational excellence and flawless delivery, working in close partnership with business development, product, and engineering teams to drive revenue growth through exceptional client outcomes. As Program Director, you will own the process management and client engagement behind these projects. You will work directly with enterprise engineering, platform, and product teams to turn a business problem into a scoped, delivered fine-tuning engagement. This is a senior, hands-on role: you will run the work yourself, not just oversee it. You will combine consulting-grade program management with a working understanding of how fine-tuning projects run, and experience navigating enterprise procurement and IT. What you’ll do Be the senior enterprise engagement lead. Run discovery with the client: stakeholder interviews, use-case prioritisation, business case and ROI, then scope and deliver the engagement end to end, including model hosting, SLAs and security reviews. Improve GenAI systems already in production, particularly across quality, cost, or latency. Take ownership of active client projects, managing scope, timelines, and stakeholders. Navigate enterprise procurement, IT infrastructure, and security processes on the client side. Our clients are tech-forward enterprises. Your counterparts are CTOs and platform, infrastructure and ML engineering leads, not procurement desks alone. Translate between client product and engineering buyers and our internal data and machine learning teams. Partner with the sales team on opportunities and help shape offerings as the business grows. Build repeatable processes and playbooks so the practice can scale across new clients and industries. Required Skills and Experience Strong consulting experience with a record of hands-on client delivery. Working technical fluency in LLMs and fine-tuning. You will partner closely with our ML engineers; you don't need to be one, and this is not a coding role. Product and process management skills, with the ability to structure ambiguous problems and drive them to completion. Experience working with large enterprises, including their procurement processes and IT infrastructure. Excellent communication skills with technical and non-technical stakeholders, including senior client leadership. STEM background preferred. Why This Role Fine-tuning needs three things: compute, which is commoditised; ML engineers, of whom there are more every year; and high-quality data, which is what actually limits model quality. Toloka produces that data, which puts us in a position which pure fine-tuning shops are not. You would join on the ground floor of this practice and help build it, including the forward-deployed team as it grows. What we can offer You will be part of an international, dynamic environment that drives innovation and sets new standards in the AI and technology sector. Competitive compensation package including base salary, bonus, and ESOP. Paid PTO and benefits will vary depending on location. We offer a full remote or hybrid model (if you are based in NL or Serbia). IT setup and home office allowances. Equal Opportunity Employer: Toloka is committed to providing equal opportunity and fostering an inclusive environment. We welcome applications from all qualified individuals and do not discriminate on the basis of race, religion, color, national origin, sex, sexual orientation, gender identity, age, marital status, veteran status, disability, or any other characteristic protected by applicable law. Selection decisions are made based on qualifications, merit, and business need. [Important Notice] Scam Alert Regarding Fake Job Postings It has come to our attention that an individual or group is fraudulently impersonating Toloka to post fake jobs and solicit personal information from applicants. Please be aware: Official Communication: Our recruiting team will only contact you from an official " toloka.ai " email address. We will NEVER use Gmail, Yahoo, Tolokainc, toloka.inc, or other personal or seemingly business email accounts. Our Process: We will never ask for your bank account details, credit card number, or any fees as part of the application or interview process. Official Listings: All legitimate job openings are posted on our official careers page: https://toloka.ai/careers#job-list What to do: If you see a suspicious job posting or have been contacted by someone you suspect is a scammer, please do not provide any personal information. Instead, report the incident to us directly at security@toloka.ai and report the profile/post to LinkedIn. We are taking this matter very seriously and are working with the appropriate parties to resolve it. Thank you for your vigilance! To learn how we collect, use, disclose, and store personal data, check out our Privacy Notice .