Strategist Lead, Agent Development

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.

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 through Carrot

• Lunch, as well as delicious snacks and coffee to keep you energized 

• 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 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.