Strategist, Agent Development – Retail

About the role

As an Agent Strategist you own how Sierra’s AI agents come to life for our retail customers, from the first pilot to a production agent handling thousands of conversations daily. You work at the intersection of product, technology and customer‑facing teams, turning complex business problems into measurable AI solutions.

Key responsibilities

• Own the Agent Development Life Cycle, guiding agents from scope through design, tooling, evaluation, launch and continuous iteration.
• Serve as a trusted strategic advisor to enterprise leaders, shaping AI strategies that drive business outcomes.
• Partner daily with customer teams, run working sessions, troubleshoot issues and keep projects on track for launch.
• Surface unmet customer needs and feed them back to product and research to influence Sierra’s roadmap.

Required profile

• Customer obsession with a proven ability to build trusted relationships in complex organizations.
• Strong communication skills, both technical and non‑technical.
• Strategic problem‑solving in ambiguous environments, with analytical and critical‑thinking abilities.
• Technical aptitude for reading API docs, understanding data models and system architecture.
• Track record of owning multiple high‑visibility projects and delivering results.

Required skills

• API integration
• Data modeling
• System architecture
• AI/LLM agent development
• Evaluation frameworks
• Retrieval‑augmented generation (RAG)
• Prompt engineering

What we offer

• Flexible (unlimited) paid time off
• Medical, dental, and vision benefits for you and your family
• Life insurance and disability coverage
• Retirement plan (where applicable)
• Parental leave and fertility/family‑building benefits
• Free lunch, snacks, and coffee