Strategist Lead, Agent Development

About this role

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 and Clay Bavor 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 Lead, you own how Sierra's AI agents come to life for our customers, from first pilot to a production agent handling thousands of conversations a day. We believe the best leaders stay hands-on and close to the work. You'll sit at the intersection of product, building agents, and customer-facing work, and stay just as close to the technology as you are to the people you build for and the team you lead. • Lead the Agent Development Life Cycle. Our leads operate as ICs for their first 2-4 months at Sierra, then evolve into the lead role, all while continuing to take agents from initial scope through conversation design, tooling, evaluation, launch, and continuous iteration in production. You'll both build directly and guide your team through the full lifecycle, coaching strategists to set and maintain the standard for ADLC best practices. You'll ensure agents launch on time, meet customer needs, and measurably move the customer's business. • Build the team as you build the business. You’ll take on two kinds of leadership: serving as the senior sponsor on our key customer deployments, and managing a team of strategists. You'll drive how the strategist function grows, from hiring and onboarding to defining what success looks like. • Be the trusted strategic advisor to enterprise leaders. Sit shoulder-to-shoulder with our customers' executives, understand what success actually means to their business, and actively build/shape the AI strategy that gets them there. You'll develop your team to do the same. • Guide delivery with the customer's working teams day to day. Run working sessions, troubleshoot agents as issues come up, and coach your team to make the calls that keep every build on track for launch. You'll be accountable for delivery quality and customer impact across your team's portfolio. • Shape the future of the product. Your team's direct work with customers will guide the evolution of Sierra's core platform. You'll surface unmet needs, prioritize initiatives, and collaborate with research, product, and platform teams to influence where Sierra goes next. What you'll bring • Customer obsession. Genuine energy being in front of customers, understanding their business and needs, thriving in complex organizations, and building trusted relationships, plus the ability to develop that muscle in others. • Communication. Clear, direct, and persuasive across technical and non-technical audiences. • Strategic problem-solving in ambiguity. Strong analytical and critical-thinking skills to break down complex problems, spot risks early, and guide teams through fast-changing, ambiguous environments. • A leadership style that comes from being hands-on. You blend high standards with empathy, fostering both speed and quality across your team. • Technical aptitude. Comfortable engaging directly with technical concepts (reading API documentation, understanding data models and system architecture, and following engineering tradeoffs in a design discussion). • Ownership and delivery. A track record of running, as well as leading teams that run, multiple complex, high-visibility projects at once and driving them to outcomes. • A degree in Computer Science, Engineering, Mathematics, a related technical field, or equivalent practical experience, and/or an MBA or comparable experience at the intersection of technology and business. Even better... • Experience building or deploying AI/LLM agents in production, hands-on with the tools behind them (eval frameworks, agent tooling, RAG, prompt engineering), working closely with technical counterparts. • Background as a founder, product or strategy leader, or startup operator with high ownership and urgency. • Experience managing teams in product, consulting, solutions, or other customer-facing roles. Our values • Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work. • Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it. • Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve. • Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time. • Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements. What we offer We want our benefits to reflect our values and offer the following to full-time employees: • Flexible (unlimited) paid time off • Medical, dental, and vision benefits for you and your family • Life insurance and disability benefits • Retirement plan dependent on country of employment • Parental leave • Fertility and family building benefits • Lunch, as well as delicious snacks and coffee to keep you energized when working onsite • Discretionary benefit stipend giving people the ability to spend where it matters most • Free alphorn lessons These benefits are further detailed in Sierra's policies, may vary by region and employment type, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra's equity plans subject to the terms of the applicable plans and policies. Be you, with us We're working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply through the link on this page even if your experience doesn't precisely match the job description. Sierra is a proud equal opportunity employer. All qualified applicants will receive consideration for employment without regard to any characteristic protected by applicable federal, state or local laws, including veteran status and disability status. Hiring decisions are made by people, based on merit. If you need a reasonable accommodation for a disability, a religious practice, pregnancy or any related condition at any point in the application or interview process, contact us at accommodations@sierra.ai. Requests are handled confidentially and do not affect your candidacy. We will consider qualified applicants with arrest and conviction records in accordance with applicable fair chance laws.