Strategist, Agent Development - Flagship Deployment

Sierra•San Francisco, CA

9d•$200,000 - $290,000•Onsite

About The Position

Sierra is the leading platform for customer-facing AI agents, working with many of the world's biggest brands to transform how they serve customers and grow their businesses. This role is primarily an in-person position based in San Francisco. The company is guided by values of Trust, Customer Obsession, Craftsmanship, Intensity, and a commitment to balancing Family. The co-founders are Bret Taylor and Clay Bavor, with extensive backgrounds in technology and AI. As an Agent Strategist on a Flagship Deployment, you will lead the end-to-end deployment for one of Sierra’s largest and most strategic customers. You will own how Sierra's AI agents are implemented, managing scaled deployments and new proofs of concept. This role sits at the intersection of product, agent building, and customer-facing work, requiring close engagement with both technology and people. The goal is to transform a customer's complex problems into agents that measurably improve their business.

Requirements

10+ years of relevant experience driving results in high stakes situations in an enterprise customer facing role, ideally in a dedicated, embedded model with a named enterprise account.
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.

Nice To Haves

Experience running a company, business unit, forward deployed team, or comparable experience in general management of business initiatives that require technical aptitude, strategic leadership, operational excellence, and financial outcome accountability.
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.
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.

Responsibilities

Own the Agent Development Life Cycle: Take agents from initial scope through conversation design, tooling, and evaluation, to launch and continuous iteration in production. Translate business goals into an agent that outperforms, and tune relentlessly until it's the best version of itself in the real world.
Be the trusted strategic advisor to enterprise leaders: Sit shoulder-to-shoulder with customers' executives, understand what success means to their business, and shape the AI strategy to achieve it.
Partner with the customer's working teams and executives day to day: Oversee overall program management while ensuring ongoing executive alignment on the long-term roadmap.
Navigate enterprise complexity with cross-functional teams (engineering and product): Read implications in real time, hold ground, and steer toward the right outcome in technical discussions and negotiations. Work across business units, procurement, compliance, and senior execs.
Directly impact product: Surface unmet needs from customer work and feed them back to research and platform to shape Sierra's future direction.
Manage internal resourcing requirements: Ensure the deployment is appropriately resourced today and into the future.
Drive financial success for both the customer and Sierra: Optimize value exchange, drive revenue upside for Sierra, and work internally to manage down cost to serve over time, improving margins.
Partner with Sales on commercial strategy: Identify opportunities, align resources, and be a key player in closing new business within the deployment.