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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 - Support the business of Agent Development: Serve as the strategy and operations partner to Agent Dev leadership, and bring the same operational rigor to Agent Dev that powers our Sales organization. - Stand up the operating cadence: Partner with Agent Dev leaders to provide clear visibility into business health, including pipeline, deployment progress, utilization, expansion opportunities, and risks. - Operationalize best practices for enterprise agent deployment: Help define and scale the playbook for how Sierra builds, evaluates, launches, and expands AI agents at large enterprises. - Drive account expansion strategy: Work closely with account teams to identify whitespace, prioritize expansion opportunities, and build repeatable motions that convert post-sale momentum into durable revenue growth. - Turn insight into action: Analyze complex datasets and translate findings into clear, executive-ready recommendations that drive high leverage decisions. - Build internal tooling with AI: Leverage AI-native tools such as Claude Code, Cursor, and Codex to build lightweight internal systems, automate workflows, and create operational leverage across Agent Dev. WHAT YOU’LL BRING - 5-7 years of experience in management consulting, investment banking, private equity, or strategy and operations at top-tier technology companies. - Strong analytical rigor with the ability to work with large datasets and translate analysis into executive-ready insights and clear business actions. - Demonstrated experience supporting sales, post-sales, or commercial teams in a strategy and operations capacity. - Comfort with ambiguity and fast-changing environments, with the ability to independently structure complex problems and drive them to resolution. - Commercial instinct and business judgment, with a clear understanding of how enterprise technology products are landed, deployed, and expanded. - Strong communication skills, with the ability to influence senior stakeholders and act as a trusted advisor. - A growth mindset, coachability, and willingness to roll up your sleeves. No task is too small if it helps the team win. EVEN BETTER... - Technical fluency and coding comfort: You have built apps or internal tools before and can confidently use AI coding tools such as Claude Code, Cursor, or Codex to create production-ready internal solutions. - Previous 0-1 operating experience at a growth stage technology company. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: San Francisco, CA; New York, NY Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU'LL DO - Prospecting and Lead Generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our Commercial customers and prospects to drive revenue, pipeline, and deployment capacity. - Manage Relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our customers. Serve as the primary point of contact for commercial clients, ensuring high levels of customer satisfaction. - Negotiating and Closing Complex Deal Cycles: Lead negotiations with existing customers and prospective clients, addressing objections and closing deals. Ensure all contracts and agreements are completed accurately and in a timely manner. Work closely with legal and finance teams to finalize terms and conditions. - Sales Strategy and Planning: Develop and execute sales strategies to meet or exceed sales targets. Create tailored sales presentations and proposals to address the specific needs of enterprise clients. Collaborate with the marketing team to develop and implement effective sales campaigns and presentations. - Help Define our Sales Motion: We’re an early team, and your work will directly impact how our GTM function operates and succeeds! - Collaborate Cross-Functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product. - Market Analysis: Conduct market research to identify new business opportunities. WHAT YOU'LL BRING - 5-7+ years of experience in a customer-facing sales role, either with Mid-market or SMB accounts. - 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: Canada - Remote Workplace: Remote ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. ABOUT THE RETAIL TEAM - Sierra is partnering with a large and growing number of retailers - spanning apparel and beauty, grocery and big-box, home and auto, consumer services, marketplaces, and consumer technology. Our agents help millions of shoppers and members every day: tracking and returning orders, finding the right product, booking services, and resolving issues in each brand’s own voice. - Retail is also where AI agents go beyond support to generate revenue. From product discovery and personalized recommendations to cart recovery, win-back campaigns, and in-store support that turns unanswered store calls into visits and sales, our team is redefining what an agent can do for a brand’s top line - not just its cost line. - Join us to transform how the world’s most-loved consumer brands engage their customers - and help build technology that makes shopping more personal, effortless, and delightful for everyone. WHAT YOU'LL DO - Independently drive complex enterprise deals end-to-end: Manage a broad enterprise book with strong autonomy, leading 6- and 7-figure deal cycles from prospecting to close. - Multi-thread to the C-suite: Lead VP-level conversations, build durable C-suite relationships across customer orgs, and earn credibility quickly with new stakeholders. - Manage risk proactively: Identify and manage deal risk early; build rigorous stakeholder maps for your accounts. - Make the hard calls: Partner with your manager (and, at the senior level, operate more independently) on pricing, escalation timing, exec alignment, and deal strategy — coming to the table with a point of view, not just a problem. - Leverage leadership & co-founders: Bring in Sierra's co-founders effectively for exec engagement when it moves a deal. - Raise the bar: Act as a visible, steady leader on deal teams; proactively elevate the team's standard without being asked. - Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow. WHAT YOU'LL BRING - 8- 10 years of enterprise customer-facing sales experience, identifying and closing large accounts. - Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals. - Proven ability to multi-thread and build trusted relationships across customer C-suites. - Exceptional verbal and written communication. - Analytical mindset - you analyze market trends, spot opportunities, and make data-driven decisions. EVEN BETTER... - Familiarity with the AI landscape, key players, and emerging trends. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: Dubai, United Arab Emirates We are seeking a highly organized, proactive, and professional Executive Assistant / Office Manager to support our senior leadership team, including the CEO and CFO. This role requires an individual who can efficiently manage executive schedules, coordinate high-level meetings, oversee administrative operations, and ensure the smooth functioning of the management office. The ideal candidate will have at least 5 years of experience as an Executive Assistant or Office Manager , with previous experience in a real estate development company strongly preferred . The successful candidate must demonstrate exceptional organizational skills, discretion when handling confidential information, and the ability to work in a fast-paced, high-performance environment. Key Responsibilities Provide comprehensive executive support to the CEO and CFO. Manage complex calendars, appointments, and meeting schedules. Coordinate domestic and international travel arrangements, including visas, flights, accommodations, and itineraries. Prepare meeting agendas, presentations, reports, and executive correspondence. Record meeting minutes and follow up on action items to ensure timely completion. Act as the primary point of contact between executives and internal/external stakeholders. Manage confidential documents and sensitive business information with the highest level of discretion. Coordinate board meetings, investor meetings, and executive presentations. Oversee the day-to-day operations of the executive office, ensuring smooth administrative processes. Organize company events, executive meetings, and business functions. Liaise with various departments to ensure projects and executive requests are completed on time. Monitor office supplies, vendor relationships, and administrative budgets where applicable. Assist with special projects and strategic initiatives as assigned by management. Requirements Bachelor's degree in Business Administration or a related field is preferred. Minimum 5 years of experience as an Executive Assistant, Personal Assistant, or Office Manager. Previous experience within a real estate development, construction, or property development company is highly preferred. Experience supporting C-level executives (CEO, CFO, Chairman, or Managing Director). Excellent written and verbal communication skills in English. Strong organizational and multitasking abilities. High level of professionalism, confidentiality, and attention to detail. Advanced proficiency in Microsoft Office Suite (Excel, PowerPoint, Word, Outlook). Experience preparing reports, presentations, and executive documentation. Ability to prioritize multiple tasks and work under pressure. Strong problem-solving and interpersonal skills. UAE experience will be considered a strong advantage. Benefits Competitive salary package Employment visa Medical insurance Opportunity to work directly with senior leadership Professional and dynamic work environment Career growth within a leading real estate development company

Location: United States Company Intro At Toloka AI we create data that powers leading GenAI models and innovations. We work with frontier labs, big tech, renowned AI startups, enterprises and non-profit research organizations worldwide. We use a combination of Experts + Crowd + Tech Platform to teach AI models to reason and evaluate their efficacy and safety. We have experts in more than 50 different domains—from doctors and lawyers to physicists and engineers—and boast one of the most diverse global crowds, representing over 100 countries and speaking 40+ languages . We are a well-funded startup with an enviable portfolio of clients including Anthropic , Amazon , Microsoft , Poolside , Recraft ,  and Shopify . Recently, we secured strategic investment led by Bezos Expeditions 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 position The Forward Deployed AI Engineer is Toloka's most senior client-facing technical role. You will partner directly with CTOs, VPs of Engineering and ML, research leaders, and applied AI teams, helping them solve complex AI data challenges and translate ambitious model goals into practical, scalable solutions. This is a hands-on role . You will design and build the data-generation , labeling , and evaluation pipelines t hat power the next generation of AI models . Rather than training the models yourself, you'll help clients identify the right data strategy and own the solution from problem discovery through implementation and delivery. Beyond delivering client solutions, you'll help shape how Toloka approaches AI solution engineering - establishing best practices, raising the technical bar across engagements, and mentoring Solution Engineers and Technical Consultants . Why this role is different Every engagement is different. One week you might be designing evaluation pipelines for frontier foundation models, the next helping an enterprise build domain-specific reasoning datasets or synthetic data workflows. This role sits at the intersection of consulting, engineering, and AI. You'll work directly with some of the world's leading AI companies, helping shape how next-generation models are trained and evaluated. What you'll do Executive partnership Act as the primary technical counterpart to CTOs, VPs of Engineering, and research/engineering leadership. Lead executive conversations using a structured, answer-first (BLUF) approach. Manage escalations and expectations with composure and integrity. Build long-term trusted relationships by recommending evidence-based solutions. Data strategy & needs diagnosis Ask excellent questions to uncover the client's real need - the "question behind the question." Understand their model, which metrics they want to move, and how they intend to train or evaluate it. Draw on a solid understanding of how LLMs are trained and fine-tuned to have credible conversations with their technical leaders, understand their data strategy, and proactively propose the data that will solve their problem - with options and rationale ("based on your goal, you likely need this, or this"). Solution engineering & delivery (hands-on) Design and build the data solutions yourself: configure data-labeling components and quality controls, develop user interfaces and AI-driven solutions (e.g. agentic systems, RAG, synthetic data generation), and integrate them into automated, multi-stage pipelines that produce data for AI training and evaluation. Architect and reason about complex, multi-stage solutions end to end; run experiments to prove the pipeline delivers data of the required quality and speed; iterate from MVP toward production. Provide technical leadership across multiple client engagements, establish reusable engineering standards and best practices, and mentor Solution Engineers and Technical Consultants to raise the overall technical bar of the organization. Commercial ownership Own delivery end to end - timelines, quality, and scalability - and the commercial outcome : Gross Margin and Contribution Margin, with the levers, trade-offs, and next checkpoints named, not just described. Identify and drive expansion opportunities. About You No one is expected to meet every requirement below. If you bring a strong combination of client-facing communication, AI/LLM expertise, and hands-on engineering experience, we'd love to hear from you. Executive communication. You can confidently lead conversations with CTOs, VPs, and senior technical stakeholders - clear, concise, structured, persuasive, and calm under pressure. Professional English (C1+) is essential. Strong understanding of modern LLM development. You understand how modern LLMs are trained, fine-tuned, and evaluated (including SFT, RLHF/RLAIF, DPO/PPO, reward modeling, and LoRA/PEFT). You're comfortable discussing these topics with senior technical stakeholders and translating their goals into effective AI data solutions. Hands-on solution engineering. You've designed complex AI solutions, built multi-stage pipelines, and developed AI-driven systems (e.g. agentic workflows, RAG, or synthetic data generation). You're comfortable working in Python (NumPy, Pandas), integrating APIs, and independently prototyping LLM-powered solutions. Solid software engineering foundations. You understand version control, testing, MVP thinking, and iterative development. Experience building production software is a strong plus. Exceptional discovery and problem framing. You enjoy working through ambiguity, asking the right questions, and translating business or research goals into clear AI data and evaluation strategies. Seniority and track record. 8+ years delivering complex AI, ML, or data projects end to end, with experience influencing technical direction beyond individual projects. Experience establishing engineering standards, mentoring engineers, or leading cross-functional technical initiatives is highly valued. Experience in top-tier strategy consulting (McKinsey, Bain, BCG) and/or as an applied ML / LLM engineer is a strong advantage. Ownership mindset. You take responsibility for outcomes, make thoughtful trade-offs between time, cost, and quality, and are comfortable owning both technical and commercial success. Nice to have Hands-on experience training or fine-tuning LLMs and/or building agentic systems (helps you reason about client needs - though the role itself is about building data solutions, not training models). Advanced degree (MSc/PhD) in AI, CS, or a related field. Experience in crowdsourcing and/or data-centric AI, and with fast-paced, multi-project delivery for frontier AI clients. What we can offer Freelance (B2B) collaboration , with a path into a project team if things go well; Flexible, fully remote schedule ( 40 hours per week ); Work at the leading edge of AI development, alongside a dedicated and dynamic team of experts; Projects with customers that are AI industry leaders and well-known household names; Friendly community. [Important Notice] Scam Alert Regarding Fake Job Postings It has come to our attention that an individual or group is fraudulently impersonating Toloka to post fake jobs and solicit personal information from applicants.Please be aware: Official Communication: Our recruiting team will only contact you from an official " toloka.ai " email address. We will NEVER use Gmail, Yahoo, Tolokainc, toloka.inc,  or other personal or seemingly business email accounts. Our Process: We will never ask for your bank account details, credit card number, or any fees as part of the application or interview process. Official Listings: All legitimate job openings are posted on our official careers page: https://toloka.ai/careers#job-list What to do: If you see a suspicious job posting or have been contacted by someone you suspect is a scammer, please do not provide any personal information. Instead, report the incident to us directly at security@toloka.ai and report the profile/post to LinkedIn.We are taking this matter very seriously and are working with the appropriate parties to resolve it. Thank you for your vigilance! To learn how we collect, use, disclose, and store personal data, check out our Privacy Notice .

Location: US - Remote; San Francisco, CA; New York, NY; Atlanta, GA Workplace: Remote ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. ABOUT THE RETAIL TEAM - Sierra is partnering with a large and growing number of retailers - spanning apparel and beauty, grocery and big-box, home and auto, consumer services, marketplaces, and consumer technology. Our agents help millions of shoppers and members every day: tracking and returning orders, finding the right product, booking services, and resolving issues in each brand’s own voice. - Retail is also where AI agents go beyond support to generate revenue. From product discovery and personalized recommendations to cart recovery, win-back campaigns, and in-store support that turns unanswered store calls into visits and sales, our team is redefining what an agent can do for a brand’s top line - not just its cost line. - Join us to transform how the world’s most-loved consumer brands engage their customers - and help build technology that makes shopping more personal, effortless, and delightful for everyone. WHAT YOU'LL DO - Lead & develop a high-performing sales team: Hire, onboard, and develop AEs across your region, Coach reps on deal strategy, pipeline management, and execution. Create a culture of accountability, learning, and collaboration. Identify and grow future leaders on your team. - Own regional performance: Own your regional number and forecast accuracy, Inspect pipeline quality and help unblock stalled deals. Drive consistent execution of our sales process. Partner with RevOps to ensure clean data and clear insights. - Be deeply involved in deals: Join key customer and prospect conversations. Help reps navigate complex buying committees and late-stage deals. Support pricing, negotiation, and close strategy. WHAT YOU'LL BRING - 10-15+ years of experience: Extensive experience in enterprise customer-facing sales role, identifying and closing large accounts. - People leadership experience: 5+ years managing, mentoring, and developing a high-performing enterprise sales team. - Enterprise experience: You've run and managed end-to-end complex deals ($1M+). - Strong communication skills: Exceptional verbal and written communication abilities. - Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions. EVEN BETTER... - Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends, as well as fluency with AI tooling and workflows. - Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early stage growth. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - 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: US - Remote; San Francisco, CA; New York, NY; Atlanta, GA Workplace: Remote ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. ABOUT THE HEALTHCARE TEAM - Our healthcare agents already reach over 50% of U.S. families. We partner with leading health plans, providers, and healthcare platforms to deliver AI agents that handle some of the most sensitive and high stakes conversations in any industry. From helping members understand their benefits to resolving billing questions with empathy, our healthcare agents are transforming how patients and policyholders interact with the healthcare system. - Our healthcare customers include major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms. - Join us to transform the patient experience across the healthcare system—and help build technology that makes care more accessible, more human and more affordable for everyone. WHAT YOU'LL DO - Lead & develop a high-performing sales team: Hire, onboard, and develop AEs across your region, Coach reps on deal strategy, pipeline management, and execution. Create a culture of accountability, learning, and collaboration. Identify and grow future leaders on your team. - Own regional performance: Own your regional number and forecast accuracy, Inspect pipeline quality and help unblock stalled deals. Drive consistent execution of our sales process. Partner with RevOps to ensure clean data and clear insights. - Be deeply involved in deals: Join key customer and prospect conversations. Help reps navigate complex buying committees and late-stage deals. Support pricing, negotiation, and close strategy. WHAT YOU'LL BRING - 10-15+ years of experience: Extensive experience in enterprise customer-facing sales role, identifying and closing large accounts. - People leadership experience: 5+ years managing, mentoring, and developing a high-performing enterprise sales team. - Enterprise experience: You've run and managed end-to-end complex deals ($1M+). - Strong communication skills: Exceptional verbal and written communication abilities. - Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions. EVEN BETTER... - Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends, as well as fluency with AI tooling and workflows. - Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early stage growth. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - 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: US - Remote; San Francisco, CA; New York, NY; Atlanta, GA Workplace: Remote ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. ABOUT THE RETAIL TEAM - Sierra is partnering with a large and growing number of retailers - spanning apparel and beauty, grocery and big-box, home and auto, consumer services, marketplaces, and consumer technology. Our agents help millions of shoppers and members every day: tracking and returning orders, finding the right product, booking services, and resolving issues in each brand’s own voice. - Retail is also where AI agents go beyond support to generate revenue. From product discovery and personalized recommendations to cart recovery, win-back campaigns, and in-store support that turns unanswered store calls into visits and sales, our team is redefining what an agent can do for a brand’s top line - not just its cost line. - Join us to transform how the world’s most-loved consumer brands engage their customers - and help build technology that makes shopping more personal, effortless, and delightful for everyone. WHAT YOU'LL DO - Independently drive complex enterprise deals end-to-end: Manage a broad enterprise book with strong autonomy, leading 6- and 7-figure deal cycles from prospecting to close. - Multi-thread to the C-suite: Lead VP-level conversations, build durable C-suite relationships across customer orgs, and earn credibility quickly with new stakeholders. - Manage risk proactively: Identify and manage deal risk early; build rigorous stakeholder maps for your accounts. - Make the hard calls: Partner with your manager (and, at the senior level, operate more independently) on pricing, escalation timing, exec alignment, and deal strategy — coming to the table with a point of view, not just a problem. - Leverage leadership & co-founders: Bring in Sierra's co-founders effectively for exec engagement when it moves a deal. - Raise the bar: Act as a visible, steady leader on deal teams; proactively elevate the team's standard without being asked. - Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow. WHAT YOU'LL BRING - 8- 10 years of enterprise customer-facing sales experience, identifying and closing large accounts. - Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals. - Proven ability to multi-thread and build trusted relationships across customer C-suites. - Exceptional verbal and written communication. - Analytical mindset - you analyze market trends, spot opportunities, and make data-driven decisions. EVEN BETTER... - Familiarity with the AI landscape, key players, and emerging trends. 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: US - Remote; San Francisco, CA; New York, NY; Atlanta, GA Workplace: Remote ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. ABOUT THE HEALTHCARE TEAM - Our healthcare agents already reach over 50% of U.S. families. We partner with leading health plans, providers, and healthcare platforms to deliver AI agents that handle some of the most sensitive and high stakes conversations in any industry. From helping members understand their benefits to resolving billing questions with empathy, our healthcare agents are transforming how patients and policyholders interact with the healthcare system. - Our healthcare customers include major health insurance networks, nonprofit providers, multi-site primary and urgent care practices, healthcare diagnostics companies, and healthcare financial platforms. - Join us to transform the patient experience across the healthcare system—and help build technology that makes care more accessible, more human and more affordable for everyone. WHAT YOU'LL DO - Independently drive complex enterprise deals end-to-end: Manage a broad enterprise book with strong autonomy, leading 6- and 7-figure deal cycles from prospecting to close. - Multi-thread to the C-suite: Lead VP-level conversations, build durable C-suite relationships across customer orgs, and earn credibility quickly with new stakeholders. - Manage risk proactively: Identify and manage deal risk early; build rigorous stakeholder maps for your accounts. - Make the hard calls: Partner with your manager (and, at the senior level, operate more independently) on pricing, escalation timing, exec alignment, and deal strategy — coming to the table with a point of view, not just a problem. - Leverage leadership & co-founders: Bring in Sierra's co-founders effectively for exec engagement when it moves a deal. - Raise the bar: Act as a visible, steady leader on deal teams; proactively elevate the team's standard without being asked. - Operate as an AI-native seller: Leverage AI tools across the full sales cycle- account research, personalized outreach, call summarization, pipeline forecasting, and deal execution- to automate low-value tasks and reinvest that time into high-value customer relationships, while continuously adopting and experimenting with new tools to work faster and smarter than traditional methods allow. WHAT YOU'LL BRING - 8- 10 years of enterprise customer-facing sales experience, identifying and closing large accounts. - Experience managing a $1M+ quota and running end-to-end complex 6- and 7-figure ACV deals. - Proven ability to multi-thread and build trusted relationships across customer C-suites. - Exceptional verbal and written communication. - Analytical mindset - you analyze market trends, spot opportunities, and make data-driven decisions. EVEN BETTER... - Familiarity with the AI landscape, key players, and emerging trends. 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 - Build the third-party event portfolio: Own Sierra's strategy for industry conferences and sponsorships across our key verticals. Decide where we show up and why—evaluating each opportunity against pipeline goals, audience fit, and brand impact—and shape a portfolio of third-party events that builds our presence in the industries that matter most. - Program high-impact event experiences: Design the formats that drive real conversations with enterprise buyers—executive roundtables, panels, fireside chats, dinners, and field events—and define the content and messaging behind them. Develop our booth content and on-site narrative so every touchpoint reflects our brand and clearly tells the Sierra story. - Own sales enablement for events: Partner closely with Sales to make events a true pipeline engine. Build the pre-event targeting and outreach, equip the field with talk tracks and materials, and develop the post-event templates, follow-up sequences, and handoff motions that turn conversations into meetings and opportunities. - Think in integrated campaigns: Treat events as one channel in a larger story rather than standalone moments. Connect each event to the broader marketing campaign—content, demand gen, social, and ABM—so our presence builds toward a coherent narrative and compounding results. - Measure and iterate: Track event performance, gather attendee and sales feedback, and turn it into reusable playbooks. Compile post-event reporting that captures what worked, what didn't, and how we make the next program sharper. WHAT YOU’LL BRING - 5+ years of event marketing experience planning and executing corporate events, ideally in-house, though agency experience will also be considered. - A strategic track record building event programs that drive measurable pipeline—not just well-run logistics, but a clear point of view on which events to invest in and why. - Experience designing and programming event formats (roundtables, panels, fireside chats, field events) and developing the content and messaging that make them land with senior audiences. - A strong partnership instinct with Sales: you understand how events feed pipeline and can build the targeting, outreach, enablement, and follow-up that convert attendees into opportunities. - Demonstrated ability to manage producers, agencies, vendors, and conference/sponsorship relationships—directing execution to a high bar without owning every logistical detail yourself. - Exceptional organizational skills and meticulous attention to detail, with the ability to juggle multiple events, timelines, and partners at once without missing a beat. - Strong communication and teamwork skills, with the ability to articulate plans, campaign logic, and post-event insights to all levels of the organization. - Enthusiasm for managing events nationwide or internationally, with the flexibility to accommodate a dynamic event calendar that requires regular travel. EVEN BETTER… - Integrated campaign experience: A history of connecting events to broader demand gen, content, and ABM programs so they reinforce a single, compounding narrative. - Enterprise and field marketing experience: Familiarity with creating targeted, high-impact initiatives designed specifically for enterprise customers, aligned closely with sales teams and strategic business objectives. - A proactive attitude: Ability to thrive in a fast-paced environment with high expectations. You are resourceful and calm under pressure, willing to roll up your sleeves and solve challenges on the fly. - Passion for Sierra's mission and brand: A creative flair for designing event experiences that embody our values and leave a lasting impression. You take pride in building an events portfolio that showcases Sierra's innovation and company values. 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: Paris 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 - Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity.   - Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations. - Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, addressing objections and closing deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders. - Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers needs. Collaborate with our marketing team to implement effective sales campaigns and presentations. - Help define our sales motion: We’re an early team, and your work will directly impact how our GTM function operates and succeeds.  - Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product. WHAT YOU'LL BRING - 10+ years of experience in an enterprise customer-facing sales role, identifying and closing large accounts. - Strong communication skills: Exceptional verbal and written communication abilities. Professional fluency in French and English. - Enterprise experience: Experience managing a $1M+ quota, and running end-to-end complex deals. - Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions. - Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling. EVEN BETTER... - Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends. - Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early stage growth. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - 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 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 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 position The Forward Deployed AI Engineer Engineer is Toloka's most senior client-facing technical role. You will partner directly with CTOs, VPs of Engineering and ML, research leaders, and applied AI teams, helping them solve complex AI data challenges and translate ambitious model goals into practical, scalable solutions. This is a hands-on role . You will design and build the data-generation , labeling , and evaluation pipelines t hat power the next generation of AI models . Rather than training the models yourself, you'll help clients identify the right data strategy and own the solution from problem discovery through implementation and delivery. Beyond delivering client solutions, you'll help shape how Toloka approaches AI solution engineering - establishing best practices, raising the technical bar across engagements, and mentoring Solution Engineers and Technical Consultants . Why this role is different Every engagement is different. One week you might be designing evaluation pipelines for frontier foundation models, the next helping an enterprise build domain-specific reasoning datasets or synthetic data workflows. This role sits at the intersection of consulting, engineering, and AI. You'll work directly with some of the world's leading AI companies, helping shape how next-generation models are trained and evaluated. What you'll do Executive partnership Act as the primary technical counterpart to CTOs, VPs of Engineering, and research/engineering leadership. Lead executive conversations using a structured, answer-first (BLUF) approach. Manage escalations and expectations with composure and integrity. Build long-term trusted relationships by recommending evidence-based solutions. Data strategy & needs diagnosis Ask excellent questions to uncover the client's real need - the "question behind the question." Understand their model, which metrics they want to move, and how they intend to train or evaluate it. Draw on a solid understanding of how LLMs are trained and fine-tuned to have credible conversations with their technical leaders, understand their data strategy, and proactively propose the data that will solve their problem - with options and rationale ("based on your goal, you likely need this, or this"). Solution engineering & delivery (hands-on) Design and build the data solutions yourself: configure data-labeling components and quality controls, develop user interfaces and AI-driven solutions (e.g. agentic systems, RAG, synthetic data generation), and integrate them into automated, multi-stage pipelines that produce data for AI training and evaluation. Architect and reason about complex, multi-stage solutions end to end; run experiments to prove the pipeline delivers data of the required quality and speed; iterate from MVP toward production. Provide technical leadership across multiple client engagements, establish reusable engineering standards and best practices, and mentor Solution Engineers and Technical Consultants to raise the overall technical bar of the organization. Commercial ownership Own delivery end to end - timelines, quality, and scalability - and the commercial outcome : Gross Margin and Contribution Margin, with the levers, trade-offs, and next checkpoints named, not just described. Identify and drive expansion opportunities. About You No one is expected to meet every requirement below. If you bring a strong combination of client-facing communication, AI/LLM expertise, and hands-on engineering experience, we'd love to hear from you. Executive communication. You can confidently lead conversations with CTOs, VPs, and senior technical stakeholders - clear, concise, structured, persuasive, and calm under pressure. Professional English (C1+) is essential. Strong understanding of modern LLM development. You understand how modern LLMs are trained, fine-tuned, and evaluated (including SFT, RLHF/RLAIF, DPO/PPO, reward modeling, and LoRA/PEFT). You're comfortable discussing these topics with senior technical stakeholders and translating their goals into effective AI data solutions. Hands-on solution engineering. You've designed complex AI solutions, built multi-stage pipelines, and developed AI-driven systems (e.g. agentic workflows, RAG, or synthetic data generation). You're comfortable working in Python (NumPy, Pandas), integrating APIs, and independently prototyping LLM-powered solutions. Solid software engineering foundations. You understand version control, testing, MVP thinking, and iterative development. Experience building production software is a strong plus. Exceptional discovery and problem framing. You enjoy working through ambiguity, asking the right questions, and translating business or research goals into clear AI data and evaluation strategies. Seniority and track record. 8+ years delivering complex AI, ML, or data projects end to end, with experience influencing technical direction beyond individual projects. Experience establishing engineering standards, mentoring engineers, or leading cross-functional technical initiatives is highly valued. Experience in top-tier strategy consulting (McKinsey, Bain, BCG) and/or as an applied ML / LLM engineer is a strong advantage. Ownership mindset. You take responsibility for outcomes, make thoughtful trade-offs between time, cost, and quality, and are comfortable owning both technical and commercial success. Nice to have Hands-on experience training or fine-tuning LLMs and/or building agentic systems (helps you reason about client needs - though the role itself is about building data solutions, not training models). Advanced degree (MSc/PhD) in AI, CS, or a related field. Experience in crowdsourcing and/or data-centric AI, and with fast-paced, multi-project delivery for frontier AI clients. What we can offer Freelance (B2B) collaboration , with a path into a project team if things go well; Flexible, fully remote schedule ( 40 hours per week ); Work at the leading edge of AI development, alongside a dedicated and dynamic team of experts; Projects with customers that are AI industry leaders and well-known household names; Friendly community. [Important Notice] Scam Alert Regarding Fake Job Postings It has come to our attention that an individual or group is fraudulently impersonating Toloka to post fake jobs and solicit personal information from applicants.Please be aware: Official Communication: Our recruiting team will only contact you from an official " toloka.ai " email address. We will NEVER use Gmail, Yahoo, Tolokainc, toloka.inc,  or other personal or seemingly business email accounts. Our Process: We will never ask for your bank account details, credit card number, or any fees as part of the application or interview process. Official Listings: All legitimate job openings are posted on our official careers page: https://toloka.ai/careers#job-list To learn how we collect, use, disclose, and store personal data, check out our Privacy Notice . 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 - Employee Relations: Serve as a key resource for employees and managers, providing guidance on HR policies, addressing and resolving employee conflicts, and fostering a positive and productive work environment. - HR Administration: Manage HR systems, maintain accurate employee records, benefits enrollment, and generating HR reports. - Employee Onboarding: Ensure a seamless experience from candidate offer approval to new hire start date. - HR Policy Implementation: Develop and ensure the effective implementation of HR policies and procedures across Sierra, ensuring alignment with legal requirements and company values. - Employee Engagement: Design and implement employee engagement programs to enhance employee satisfaction and foster transparent and effective communication. - Organizational design: (structuring teams for efficiency and scalability, defining roles and responsibilities, aligning talent with business strategy), strategic thinking, coaching, business acumen WHAT YOU’LL BRING - 5+ years of experience in human resources or people operations, ideally in a fast-growing environment supporting Sales organizations. - Demonstrated expertise and understanding of HR best practices, employment laws, and regulation. - Excellent organizational skills, attention to detail, and ability to manage multiple priorities in a fast-paced environment. - Proactive, innovative mindset with a focus on continuous improvement and strategic impact. - Experience partnering with engineering, product, or other technical teams. EVEN BETTER… - Hands-on experience implementing HR systems and processes in a scaling company. - Exposure to international HR compliance, including global employment laws and cross-border workforce considerations. - Understanding of international compensation structures and total rewards programs. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

Location: San Francisco, CA; New York, NY Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU’LL DO - 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 Brazilian Portuguese 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: San Francisco, CA; New York, NY Workplace: OnSite ABOUT US Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands — including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank — to transform how they serve customers and grow their businesses. We are primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family along the way. These values are the foundation of our work, and we are committed to upholding them in everything we do. Sierra was co-founded by Bret Taylor https://www.linkedin.com/in/brettaylor/ and Clay Bavor https://www.linkedin.com/in/claybavor/ who first met while working together at Google over 20 years ago. Bret currently serves as Chairman of the Board of Open AI. Previously, he was co-CEO of Salesforce and CTO of Facebook. Clay spent 18 years at Google, where he most recently led Google Labs. WHAT YOU'LL DO - Build enterprise-grade AI agents: As an Agent PM at Sierra, you will be responsible for partnering directly with our engineers and customers to build and ship AI agents that handle thousands of customer conversations a day. - Engage with customers: In the role, you will engage with all levels of our customers’ businesses: - Discover and assess their requirements. - Prepare and present demonstrations of Sierra’s agent. - Address and overcome technical challenges in the business process by working with technical counterparts. - Develop and improve Sierra virtual agents to fit and anticipate our customers’ needs and business processes. - Become trusted advisors and drive strategic technical strategies for our customers. - Shape the product roadmap: Work with Sierra’s engineering and product development teams to scope and implement new features essential to the success of your customers. WHAT YOU'LL BRING - 5-7+ years experience in product development of highly technical products. - Past experience in Product Management or other similar product development roles at or above the level of Senior Product Manager. - Experience crafting and tailoring a message for potential customers, including executives. - Ability to communicate highly technical concepts to both non-technical and technically proficient audiences, including recent AI developments. - Professional fluency in both Brazilian Portuguese and English. - Degree in a technical or related field, or equivalent professional experience. EVEN BETTER... - AI-related experience (experience with product development for AI agents a plus). - Some coding experience with React, Typescript, and Go. - MBA or equivalent professional experience (while this is a product management role, you will have the opportunity to lean into broader business roles). - Past roles that interface with end customers to influence software development. OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

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

Location: San Francisco, CA 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. The role This is a foundational role on Sierra's Operations team, sitting at the intersection of marketing and GTM. As Marketing Operations and Analytics Lead, you'll own two things: the measurement infrastructure that connects marketing programs to pipeline and revenue; and the operational processes that make the marketing engine run efficiently and at scale. What you'll do - Full-funnel attribution: Design and own Sierra's marketing attribution framework, connecting campaigns, events, content, and demand gen programs to pipeline generation and ultimately LTC conversions. - Pipeline analytics: Partner with Marketing and Sales to analyze pipegen by vertical, region, and segment. Track conversion rates at each stage and surface where marketing programs are—and aren't—generating high-quality opportunities. - Performance reporting: Build and maintain the marketing team's core performance dashboards—campaign ROI, event pipeline influence, channel mix, lead quality, and funnel velocity. - ICP & account intelligence: Develop data-driven ICP scoring and account prioritization models to focus marketing investment on segments with the highest win rates and ASPs. Integrate signals from first-party and third-party intent sources to keep targeting sharp. - Experiment design & optimization: Design rigorous A/B and multivariate tests across marketing channels. Establish the statistical standards the team uses to evaluate new programs; translate results into clear, actionable recommendations—not just p-values. - Lead management & routing: Define and maintain lead scoring models, MQL thresholds, and routing logic from first touch to Sales handoff. Partner with Sales to ensure lead quality, minimize friction, and continuously improve conversion from MQL to pipeline. - Campaign operations: Own the operational infrastructure behind campaign execution—email programs, landing page workflows, event lead capture, and list management. Build processes that let the demand gen and events teams move quickly without creating data debt. - Cross-functional partnership: Serve as the analytical and operational bridge between Marketing, GTM Ops, Finance, and Sales leadership—ensuring marketing metrics are aligned with company PG, POC, and ARR targets; contribute to quarterly business reviews (QBRs) and annual planning with marketing-specific performance analysis and forecasts What you'll bring - 12+ years spanning marketing analytics and marketing operations - Deep expertise in attribution modeling, multi-touch funnel analysis, and pipeline/revenue measurement in long, multi-stage enterprise sales cycles - Hands-on martech stack experience—marketing automation (Marketo, HubSpot, or similar), Salesforce, lead routing, and third-party enrichment tools - Strong SQL skills; fluency working with large datasets in modern data stacks (ClickHouse, Snowflake, BigQuery, or similar) - Proven ability to translate complex analyses into clear narratives for non-technical stakeholders, including C-suite executives - High attention to detail and a strong point of view on what "good" looks like—you've built this infrastructure before and know where the landmines are OUR VALUES - Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. - Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. - Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. - Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. - Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. WHAT WE OFFER We want our benefits to reflect our values and offer the following to full-time employees: - Flexible (unlimited) paid time off - Medical, dental, and vision benefits for you and your family - Life insurance and disability benefits - Retirement plan dependent on country of employment - Parental leave - Fertility and family building benefits - Lunch, as well as delicious snacks and coffee to keep you energized when working onsite - Discretionary benefit stipend giving people the ability to spend where it matters most - Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. BE YOU, WITH US We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.

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