Entry Level Python Developer Jobs in Shrewsbury, MA

At WHOOP, we're on a mission to unlock human performance and healthspan. WHOOP uses AI to transform continuous physiological data into clear, personalized insights and recommendations members can act on every day. Our AI experiences, including WHOOP Coach, turn raw signals into trusted guidance, and the agents behind them are only as good as the prompts, knowledge, and evaluation that shape them.
WHOOP's AI coaching experiences are growing quickly, and their quality rests on a layer of work that's easy to under-resource: the prompts, evaluations, and knowledge bases that shape how our agents behave. Today that work happens on the side of people's desks, and it has outgrown what a side-of-desk job can cover. This role gives it a dedicated, hands-on owner. We're hiring early-career on purpose, optimizing for curiosity, learning agility, and excitement about WHOOP and AI over years of product experience; deep product strategy is not the bar for this role.
WHOOP is hiring an AI Product Specialist to help build and continuously improve the AI agents behind WHOOP Coach and our other AI-powered experiences. This is an entry-level, hands-on product role: you'll work in our internal tools, writing and refining prompts, building and running evaluations, and curating the knowledge bases that ground our agents, partnering with Product Managers and AI Engineers to make the Coach more correct, personalized, and trustworthy. We're hiring for curiosity and excitement about WHOOP and AI, not years of experience.
RESPONSIBILITIES

• Write, test, and iterate prompts and agent instructions that shape how WHOOP's AI agents behave.
• Source, structure, and maintain the knowledge bases that ground our agents, keeping them accurate and current.
• Build evaluation cases and datasets from real usage and edge cases, and run them in our internal tooling.
• Read traces, spot failure patterns, and help diagnose where agents break: prompt, retrieval, context, or tools.
• Help tell the difference between "passes our evals" and "actually feels good to a member."
• Partner with PMs, AI Engineers, Analytics, and Design, turning their needs into concrete agent improvements.

QUALIFICATIONS

• Excitement about WHOOP and our mission: you use it (or can't wait to) and care about member health.
• Curiosity about AI: you use these tools yourself and want to understand why they behave the way they do.
• A track record of teaching yourself new tools quickly; you learn by doing.
• Precise, clear writing; you notice when language is ambiguous and tighten it.
• Good judgment, especially around safety and responsibility in a health context.
• Comfort with ambiguity and a bias toward making fuzzy problems concrete.
• No prior product or AI work experience required. Nice to have: hands-on experience with LLMs, prompts, RAG, or AI agents; light scripting (e.g., 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.
Interested in the role, but don't meet every qualification? We encourage you to still 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 to determine employment eligibilityThe WHOOP compensation philosophy is designed to attract, motivate, and retain exceptional talent by offering competitive base salaries, meaningful equity, and consistent pay practices that reflect our mission and core values.
At WHOOP, we view total compensation as the combination of base salary, equity, and benefits, with equity serving as a key differentiator that aligns our employees with the long-term success of the company and allows every member of our corporate team to own part of WHOOP and share in the company's long-term growth and success.
The U.S. base salary range for this full-time position is $90,000.00 - $120,000.00. Salary ranges are determined by role, level, and location. Within each range, individual pay is based on factors such as job-related skills, experience, performance, and relevant education or training. In addition to the base salary, the successful candidate will also receive benefits and a generous equity package. These ranges may be modified in the future to reflect evolving market