Strategist, Agent Development

Sierra is hiring a Strategist, Agent Development to bring customer-facing AI agents from initial pilot to production, where they may handle thousands of conversations a day. The role combines agent development, product work and direct engagement with enterprise customers to deliver measurable business outcomes.

Responsibilities

• Own the agent development life cycle: scope customer needs, design conversations, develop tooling, evaluate performance, launch agents and iterate in production.
• Advise enterprise leaders on business goals and AI strategy. Run working sessions with customer teams, troubleshoot issues and keep builds on track for launch.
• Share unmet customer needs with Sierra’s research and platform teams to inform product development.
• Potential projects include subscription-retention agents, commerce agents that troubleshoot devices and personalize recommendations, and financial-services agents for complex, regulated interactions. Define evaluation standards and use outcome metrics to improve agent performance.

Qualifications

• Strong customer focus, persuasive communication with technical and non-technical audiences, and analytical problem-solving in ambiguous situations.
• Ability to read API documentation, understand data models and system architecture, and discuss engineering tradeoffs. A track record of delivering multiple complex, high-visibility projects is required.
• Preferred: experience building or deploying AI or LLM agents in production, including evaluation frameworks, agent tooling, RAG or prompt engineering; founder, founding-team or operator experience; and a degree in Computer Science, Engineering, Mathematics or a related field, equivalent practical experience, and/or an MBA or comparable technology-and-business experience.

This is a full-time, on-site role in San Francisco, CA or New York, NY. Compensation is USD $200,000–$290,000 per year, with equity offered. Benefits for full-time employees include flexible paid time off, health coverage, insurance, parental and fertility benefits, a retirement plan dependent on country of employment, meals and a discretionary stipend; benefits may vary by region.