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 students life

Kids shouldnt 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 theyre excited to live. If you join Cartwheel youll help make this vision a reality for millions of students across the country. Were backed by top investors including Menlo Ventures General Catalyst Reach Capital and A Street Ventures and were 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 DesignEngineering & 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 01 product initiatives.

WHAT YOULL DO:

• Lead 01 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 01 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 YOULL LOVE CARTWHEEL

Our hope is that Cartwheel will be your best career addition to tackling one of the biggest challenges of our time at a company well-positioned to do so youll have:

• Mission-oriented and inclusive colleagues who will go to bat for you
• Competitive compensation between $120000 - $170000 (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

Cartwheel is proud to be an equal opportunity employer. We embrace diverse backgrounds and perspectives and an inclusive work environment. Were committed to equal employment opportunity regardless of race color religion ancestry national origin gender sexual orientation disability status or veteran status.

We participate in E-Verify. Please be prepared to provide acceptable documentation to verify your identity and work authorization

Note: Please do not contact our Care Provider or Patient Services lines regarding job postings or application status. These teams support our patients and families and are not involved in the hiring process. For all recruitment-related questions please email