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Sierra is the leading platform for customer-facing AI agents, partnering with major brands including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank. The company is headquartered in San Francisco with growing offices across North America, Europe, and Asia.
As a Strategist in Agent Development for the Retail team, you will own how Sierra's AI agents come to life for customers—from initial pilot through production deployment handling thousands of conversations daily. You sit at the intersection of product, technical agent building, and customer-facing work.
Key responsibilities include:
- Own the full 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 agents that measurably outperform and iterate relentlessly until optimal in the real world.
- Serve as a trusted strategic advisor to enterprise leaders. Work shoulder-to-shoulder with customer executives to understand what success means for their business and shape the AI strategy to get them there.
- Partner with customer working teams day-to-day. Run working sessions, troubleshoot agents as issues arise, and make calls that keep builds on track for launch.
- Directly impact product strategy. Surface unmet needs from customer work and feed them back to research and platform teams to shape Sierra's direction.
Example projects include: launching order management agents for national apparel brands; building shopping agents that convert support channels into revenue channels; standing up in-store support voice agents for big-box and grocery retailers; designing booking and payments agents for consumer services brands; handling order status and disputes at marketplace scale; and launching outbound campaigns (cart recovery, win-back, churn saves) across voice and SMS.
You will demonstrate customer obsession with genuine energy for understanding customer business needs and building trusted relationships in complex organizations. You communicate clearly and persuasively across technical and non-technical audiences. You excel at strategic problem-solving in ambiguity, breaking down complex problems, spotting risks early, and adapting as things change. You have technical aptitude—comfortable with API documentation, data models, system architecture, and engineering tradeoffs. You have a track record of running multiple complex, high-visibility projects and driving them to outcomes.
A strong plus is genuine interest in financial services and improving end-customer experience, with experience in fintech implementations, working inside financial institutions, or familiarity with financial services security and compliance (fair lending, PII handling, etc.).
Even better if you have: hands-on experience building or deploying AI/LLM agents in production with tools like eval frameworks, agent tooling, RAG, and prompt engineering; founding or founding-team experience; or a degree in Computer Science, Engineering, Mathematics, or related technical field (or equivalent practical experience), plus an MBA or comparable experience at the intersection of technology and business.
