Senior Product Manager, Growth & Engagement

Join Cartwheel to help tackle the student mental health crisis!

Cartwheel is tackling the youth mental health crisis with a novel school-based approach. Through our technology platform, students access evidence-based mental health care with no waitlists, school staff seamlessly collaborate with the student’s care team, and district administrators get the data and insights they need to deeply understand mental health trends on campus. This supports earlier intervention, higher student and family engagement in care, and better coordination among the trusted adults in a student's life. On the back end, Cartwheel’s funding model combines subscription funding from districts with Medicaid and commercial insurance billing. In doing so, we offset two-thirds or more of the cost of services for our districts and ensure every student can access great care.

Over the past 3 years, we've become the largest provider of school-centered telehealth nationwide, serving over 325 school districts across 15 states. We recently raised a significant Series B funding round backed by top investors including A-Street Ventures, Menlo Ventures, Reach Capital, and General Catalyst, and we're looking for mission-driven teammates as we aggressively expand our footprint and our product platform over the next 2 years across the more than 10,000 school districts and charter schools in the U.S. We believe 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 us, you'll help make this vision a reality for millions of students.

ABOUT THE ROLE

As the Senior Product Manager, Growth & Engagement, you’ll own the #1 driver of our value for our existing school district customers, directly impacting mental health access for hundreds of thousands of students. This is a hands-on role where you'll spend significant time with school counselors and administrators, translating their needs into experiments and valuable features. We’ve learned that the biggest source of value for our customers is high student & family engagement in care. Every district's contract with us includes a certain target number of students who can receive care each year, and districts want to make full use of their contract. In your first few quarters, you’ll focus on increasing contract utilization by identifying friction points, running rapid experiments, and shipping solutions that help students and families successfully engage in care. This role spans both the school district journey from initial sale through renewal and the patient journey from initial referral to care completion.

Example focus areas include:

• Top-of-funnel: Expanding who can refer students and optimizing initial referral flow
• Conversion to care: Reducing drop-off from referral to to first session (referrals don't count unless students actually get to their first session!)
• Ongoing district engagement: Keeping us top-of-mind for schools and families and ensuring high satisfaction to drive future referrals (for example, through personalized progress updates to school staff and nudges that ensure students don’t slip through the cracks)

At Cartwheel, Product teams are empowered with authority to experiment, pivot based on evidence, and ship incremental value. Success isn't measured by features shipped but by your ability to drive meaningful product outcomes which in turn drive business outcomes. To that end, you'll work directly with a dedicated pod of 4-6 engineers and 1 designer, with the autonomy to shape your team's priorities and technical approach. Over time, you will focus on additional outcomes across the care journey, such as improving session attendance and optimizing platform engagement metrics (e.g., DAUs, time on site, feature adoption).

Role type: This is a W2, Full-Time, Salaried position

Start date: October 2025

WHAT YOU'LL DO

• Develop the product vision for maximizing the value of Cartwheel for our school district customers
• Engage in continuous discovery with school staff (counselors, administrators, teachers), students/families, and Cartwheel’s care team. To drive meaningful outcomes, you’ll need to deeply understand school-family-care team dynamics.
• Map out opportunities, generate solutions, name assumptions, design experiments to test those assumptions, and iterate to refine solutions
• Example focus areas for the first few quarters include but are not limited to: Increasing the volume of new, high-intent referrals (e.g., expanding the pool of possible referrers, launching new clinical services that appeal to students and families); improving conversion to care rate for referred families (e.g., reducing drop-off throughout the onboarding flow).
• Work cross-functionally to:
• Align stakeholders around complex initiatives involving multiple external partners (school districts, families) and internal teams, building consensus around tradeoffs
• Translate treatment protocols into scalable product experiences
• Incorporate school district strategic goals into our product roadmap
• Run experiments and build new features in partnership with engineering and data
• Evaluate and experiment with novel AI use cases (e.g., between-session student engagement, referral identification, personalized collaboration with schools)

WHO YOU ARE

• 5+ years of product management experience with proven track record driving new user acquisition and optimizing conversion and retention in multi-stakeholder environments
• You work hard and hold yourself and others to a high bar in terms of speed and quality
• You’re passionate about our mission of being the trusted mental health partner to K12 schools, students, and families
• You have a strong analytical background. In particular, you can take a business outcome, identify product outcomes and leading indicators, map out an opportunity tree, name assumptions, and design rapid, data-driven experiments to test those assumptions.
• You thrive in complex problem domains involving multiple stakeholders with different needs. You’re comfortable prioritizing, navigating difficult tradeoffs (e.g., clinical quality vs. user engagement), and moving quickly through uncertainty to test and learn.
• You have experience with B2B2C and/or multi-sided marketplace products
• You are actively excited to use AI to support product development (e.g., generating, high quality specs, prototyping ideas) and to create value for our customers
• Note: Healthcare experience is not required

Please apply even if you don't meet all of the criteria. If your past experience doesn't perfectly match the job description, but you bring other relevant experience or skills, we'd still love to hear from you. You may be a great fit!

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 $165,000 - $200,000
• 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
• Direct impact on retention strategies serving hundreds of thousands of students and families

Cartwheel is proud to be an equal opportunity employer. We embrace diverse backgrounds and perspectives and an inclusive work environment. We're committed to equal employment opportunities 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.