AI Product Specialist

About the role

You are an early-career, hands-on owner of the prompts, evaluations, and knowledge bases that define how WHOOP Coach behaves. You will translate raw physiological signals into clear, personalized guidance by shaping the instructions and data that our AI agents consume. This role sits at the intersection of product, engineering, and coaching, where your curiosity and learning agility matter more than years of formal product experience. You will partner closely with PMs and AI Engineers to iterate directly on internal tools, ensuring our agents are correct, trustworthy, and grounded in real member contexts. Your primary mission is to build and continuously improve the AI agents behind WHOOP Coach and other AI-powered experiences by refining the foundational layer of prompts and knowledge. You will be responsible for sourcing, structuring, and maintaining the content that keeps our agents accurate, current, and aligned with member needs. This position is designed for someone who is excited about WHOOP, AI, and the intersection of behavior and performance, and who is ready to move work from side desks into a dedicated, scalable role.

Key facts

What you'll do

• Write, test, and iterate prompts and agent instructions that shape how WHOOP's AI agents behave in real coaching scenarios.
• Source, structure, and maintain the knowledge bases that ground our agents, ensuring information remains accurate, relevant, and aligned with member needs.
• Build evaluation cases and datasets from real usage patterns and edge cases, then run them using our internal tooling to measure agent performance.
• Read traces and logs to spot failure patterns, and help diagnose whether issues originate in prompt design, retrieval, context, or tool usage.
• Distinguish between superficial evaluation passes and experiences that genuinely feel correct and helpful to members in daily life.
• Partner with Product Managers, AI Engineers, Analytics, and Design teams to translate their requirements into concrete improvements for the Coach experience.
• Curate and refine examples, scenarios, and templates that clarify intent and improve consistency across AI interactions.
• Track changes in agent behavior over time, document observations, and communicate insights to cross-functional partners to guide product decisions.

Requirements

• You are excited about WHOOP and its mission, and you either use it now or cannot wait to see what it does for your own health and performance.
• You are curious about how AI works, and you actively use these tools yourself to understand why they behave in specific ways.
• You have a track record of teaching yourself new tools quickly and prefer to learn by doing rather than waiting for formal instruction.
• You write precisely and clearly, noticing when language is ambiguous and tightening it so that intent is unmistakable.
• You exercise good judgment, especially around safety and responsibility in a health context where recommendations can affect real people.
• You are comfortable with ambiguity and have a bias toward turning fuzzy problems into concrete, testable statements and behaviors.
• There is no prior product or AI work experience required for this role, lowering the barrier to entry for candidates who show strong potential.
• Nice to have: hands-on experience with LLMs, prompts, RAG, or AI agents; light scripting (for example, Python); or a background in behavioral science, coaching, or health.

This role is based in the WHOOP office located in Boston, MA. The successful candidate must be prepared to relocate if necessary to work out of the Boston, MA office.

If you are interested in the role but do not meet every qualification, we still encourage you to apply. At WHOOP, we believe there is much more to a candidate than what is written on paper, and we value character as much as experience. As we continue to build a diverse and inclusive environment, we encourage anyone who is interested in this role to apply.

WHOOP is an Equal Opportunity Employer and participates in E-verify https://www.e-verify.gov/ to determine employment eligibility.