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Sierra is the leading platform for customer-facing AI agents, serving major brands including The GAP, Rocket Mortgage, SoFi, Sutter Health, and SoftBank. The healthcare team specifically partners with health plans, providers, and healthcare platforms to deploy AI agents that handle sensitive, high-stakes conversations—from benefits inquiries to billing resolution—reaching over 50% of U.S. families.
As a Strategist in Agent Development, you will own the complete agent development lifecycle for healthcare customers, from initial pilot through production deployment handling thousands of daily conversations. You sit at the intersection of product, technical implementation, and customer engagement.
Key responsibilities:
- Own the full agent development lifecycle: scope definition, conversation design, tooling, evaluation, launch, and continuous production iteration. Translate business goals into agents that measurably outperform and iterate relentlessly for real-world excellence.
- Serve as trusted strategic advisor to enterprise healthcare leaders (health plans, providers, healthcare platforms). Understand their definition of success and shape AI strategy accordingly.
- Partner with customer working teams daily: run working sessions, troubleshoot agents in real time, and make decisions that keep builds on track for launch.
- Directly influence product direction by surfacing unmet customer needs and feeding insights back to research and platform teams.
Example projects include building agents for major health insurance networks handling detailed benefit questions, creating multi-site clinic appointment and Q&A agents, replacing paper intake forms with conversational experiences, and developing financial assistance eligibility agents for healthcare platforms.
You will thrive in complex organizations, build trusted relationships with executives, and drive multiple high-visibility projects simultaneously to measurable outcomes.
REQUIREMENTS:
- Customer obsession with genuine energy for understanding business needs and building trusted relationships.
- Clear, direct, persuasive communication across technical and non-technical audiences.
- Strategic problem-solving ability in ambiguity; strong analytical and critical-thinking skills to break down complex problems, spot risks early, and adapt quickly.
- Technical aptitude: comfortable with API documentation, data models, system architecture, and engineering tradeoffs in design discussions.
- Proven track record running multiple complex, high-visibility projects and driving them to outcomes.
- Genuine interest in healthcare and improving end-customer experience. Experience in healthcare technology, implementations at healthcare institutions, or familiarity with healthcare security and compliance (HIPAA, PII handling, etc.) is a strong plus.
EVEN BETTER:
- Hands-on experience building or deploying AI/LLM agents in production, including eval frameworks, agent tooling, RAG, and prompt engineering.
- Founder, founding team member, or operator experience—ability to balance craft, ownership, and speed.
- Degree in Computer Science, Engineering, Mathematics, or related technical field, or equivalent practical experience; MBA or comparable technology-business intersection experience.
