Strategist, Agent Development - Flagship Deployment
Sierra · San Francisco, CA
About this role
**ABOUT SIERRA** 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. Sierra is primarily an in-person company based in San Francisco, with growing offices across North America, Europe, and Asia. Our values are **Trust, Customer Obsession, Craftsmanship, Intensity,** and a commitment to balancing **Family**. **WHAT YOU’LL DO** As an **Agent Strategist** for a **Flagship Deployment**, you’ll lead the end-to-end deployment for one of Sierra’s largest and most strategic customers. You’ll own how Sierra’s AI agents come to life—often managing scaled deployments and new proofs of concept within the same account. You’ll sit at the intersection of product (building agents) and customer-facing work—staying close to both the technology and the people you build for. You’ll turn high-stakes, complex customer problems into agents that **measurably move the business**. **Key responsibilities** - **Own the Agent Development Life Cycle**: take agents from initial scope through conversation design, tooling, and evaluation—then launch and continuously iterate in production. - **Translate business goals into performance**: tune relentlessly until the agent is the best version of itself in the real world. - **Be a trusted strategic advisor**: partner with enterprise leaders to shape AI strategy and define what success means. - **Partner day-to-day with customer teams**: oversee program management and maintain executive alignment on the long-term roadmap. - **Navigate enterprise complexity**: work across engineering/product and across business units (including procurement, compliance, and senior execs). - **Directly impact product**: surface unmet needs from customer work and feed them back to research and platform. - **Manage internal resourcing**: ensure the deployment is appropriately resourced today and into the future. - **Drive financial success**: optimize value exchange, drive revenue upside for Sierra, and work to reduce cost-to-serve over time. - **Partner with Sales on commercial strategy**: help close new business within the deployment by identifying opportunities and aligning resources. **EXAMPLE PROJECTS** - Plan and execute on-site business reviews with Sierra cofounders at a Fortune 100 company. - Manage a portfolio of agents across a customer deployment as they scale nationally and expand use cases. - Build relationships across the customer organization to unlock high trust and drive new ARR. - Stand up an agent that troubleshoots a broken device end-to-end and personalizes product recommendations in the same conversation. - Partner with product on a net-new capability (new agent architecture or self-service tooling) using a live customer as a design partner. - Define evaluation and quality bars for a new agent and drive measurable outcome lift week over week. **WHAT YOU’LL BRING** - **10+ years** of relevant experience driving results in high-stakes, enterprise customer-facing roles—ideally in a dedicated/embedded model with a named enterprise account. - **Customer obsession**: energy in front of customers, thriving in complex organizations, building trusted relationships. - **Communication**: clear, direct, persuasive across technical and non-technical audiences. - **Strategic problem-solving in ambiguity**: strong analytical skills to spot ri
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