Senior Product Manager, AI Products

Join Cartwheel to help tackle the student mental health crisis. 

Kids spend most of their days in the classroom. And teachers and staff, who play a vital role in their development, are often the first to notice when something is off. But with 1 in 5 young people struggling with mental health, schools are getting crushed by a downward spiral in student crises and staff burnout.

With large increases in state and federal funding for healthcare innovation, schools are reimagining what mental health support can look like for their students, staff, and families. 

Cartwheel is an early-stage startup building technology-enabled mental health services that put schools at the center. We see our role as supporting both families and the on-campus school staff who see kids every day. This means:

• Earlier intervention
• Higher student and family engagement in care
• Better coordination among the trusted adults in a student’s life 

Kids shouldn't just aspire to get out of bed and drag themselves to class. They should be able to experience joy. They deserve to envision and build a life they’re excited to live. If you join Cartwheel, you’ll help make this vision a reality for millions of students across the country. We’re backed by top investors including Menlo Ventures, General Catalyst, Reach Capital, and A Street Ventures, and we're looking for mission-driven teammates to join our team.

ROLE TYPE: This is a W2, Full-Time, Salaried position

LOCATION: Boston or Chicago preferred (or remote-friendly with regular in-person user research)

START DATE: March/April 2026

ABOUT THE ROLE:

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.

WHAT YOU’LL DO:

• 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.

WHO YOU ARE:

Must have…

• 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.

Extra credit…

• 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.

WHY YOU’LL LOVE CARTWHEEL

Our hope is that Cartwheel will be your best career decision. In addition to tackling one of the biggest challenges of our time, at a company well-positioned to do so, you’ll have: 

• 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