Senior Product Manager, AI Products
About The Position
Cartwheel is building technology that supports how mental health care is delivered, coordinated, and sustained in school settings. As we grow, we are exploring new ways software can better support the operational workflows of school staff, clinicians, and care teams. We are looking for a Senior Product Manager to work on early-stage product initiatives focused on improving how complex work gets done. This is a senior individual contributor role for someone who thrives in ambiguity, is comfortable partnering closely with customers, and enjoys shaping products from the earliest stages. In this role, you will collaborate closely with Product Design,Engineering & executive leadership to prototype, test, and ship new capabilities. You will help translate real-world workflows into thoughtful product experiences, leveraging modern tools and emerging technologies to accelerate delivery while maintaining a high bar for trust, usability, and safety. Level and compensation may flex for exceptional candidates with demonstrated experience leading highly ambiguous, 0→1 product initiatives.
Requirements
- 7+ years of Product Management experience, including ownership of 0→1 SaaS products or similar internal tools (e.g., EHRs, care coordination tooling, etc.).
- Demonstrated experience building AI-enabled products or using AI tools extensively in product discovery, prototyping, or development.
- Strong comfort with workflow-heavy, operational products (e.g., healthcare, billing, care coordination, GovTech, EdTech).
- Proven ability to work directly with customers and conduct on-the-ground user research.
- Excellent product judgment and comfort making decisions with incomplete information.
- Ability to operate as a senior IC who shapes direction, not just execution.
- Strong written and verbal communication skills.
Nice To Haves
- Experience with AI-native patterns (workflow automation, copilots, decision support).
- Experience in healthcare, education, or other regulated domains.
- Familiarity with low-code / no-code tools or design-to-code workflows.
- Experience building internal tools that later became customer-facing products.
- Startup or early-stage company experience.
Responsibilities
- Lead 0→1 product development for new AI-enabled SaaS tools, from early concept through initial customer adoption.
- Partner closely with Design and Engineering to shape workflows, MVPs, and system behaviors in ambiguous problem spaces.
- Use AI prototyping and development tools to accelerate discovery, experimentation, and iteration.
- Spend time directly with school staff to understand real-world workflows and constraints.
- Design products focused on workflow automation and decision-support.
- Translate messy, real-world problems into clear product abstractions involving states, permissions, validations, and edge cases.
- Define success metrics and use qualitative and quantitative feedback to guide iteration.
- Make pragmatic tradeoffs between speed, quality, and scalability in an early-stage, scrappy environment.
- Help establish lightweight product practices that enable fast learning without unnecessary process.
Benefits
- Mission-oriented and inclusive colleagues who will go to bat for you
- Competitive compensation between $120,000 - $170,000 (Final level and compensation determined based on experience and scope)
- Generous PPO medical, vision, and dental coverage
- Generous paid time off, including company closure from Christmas-New Years (12/25-1/1)
- Paid parental leave
- 401K with employer match
- Meaningful equity ownership stake in Cartwheel
- Flexible and remote role with regular in-person retreats
- Annual learning stipend
- Macbook
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What This Job Offers
Job Type
Full-time
Career Level
Mid Level
Education Level
No Education Listed
