Vice President, Operations
Job Overview
Join Cartwheel to help tackle the student mental health crisis!
Cartwheel is the trusted mental health partner to K12 schools, students, and families. In 3 years, Cartwheel has become the nation's largest provider of mental health services in collaboration with schools, serving more than 325 school districts in 16 states. We see our role as partnering with parents and school staff to ensure:
- Earlier intervention
- Higher student and family engagement in care
- Better coordination among the trusted adults in a student’s life
- Improved health and educational outcomes
- Cost-effective and affordable care
Coming off of a strong Series B fundraise, and backed by top investors including A Street Ventures, Menlo Ventures, Reach Capital, and General Catalyst, Cartwheel is expanding significantly in 2026 to serve hundreds more school districts and hundreds of thousands of students and families.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
LOCATION:
- US Remote with preference for candidates based in Boston or in the Northeast
- Travel required for in-person quarterly planning with Senior Leadership Team and occasional in-person working sessions
REPORTS TO: Daniel Tartakovsky, Co-Founder and Chief Operating Officer
COMPENSATION: $225K-$285K cash compensation and meaningful equity stake in the company, depending on past experience
ABOUT THE ROLE
As Cartwheel’s Vice President, Operations, your responsibilities will include:
- Being the P&L owner for all of Cartwheel’s mature markets, accountable for achieving and reporting on revenue, margin and quality targets by state
- Managing and ensuring strong performance across Operations team (currently 35 FTEs across Care Ops, Health Plan Ops, and Revenue Cycle Management)
- Being accountable for key operational metrics, including:
- Time to care: ensuring families referred to Cartwheel access services quickly
- Conversion to care: ensuring families referred to Cartwheel engage in services
- Care revenue: grow total revenue from care delivery
- Care margin: increase insurance revenue and lower cost per session
- Collections: achieve gross and net revenue collections targets
- Payer contracting and credentialing: ensure clinicians are enrolled with payers quickly, accurately, and efficiently
- Team engagement: maintain strong team engagement and performance
- Serving as a member of Cartwheel’s Senior Leadership Team (SLT)
- SLT is the key strategy-setting and operating body at Cartwheel accountable for developing company goals, making key strategic decisions, championing Cartwheel’s values, and ensuring excellent delivery against goals
- Partnering cross-functionally:
- With our Clinical, People, and Finance leaders to achieve high quality, scalable, efficient service delivery
- With our R&D/Technology teams to improve our product, systems and tools, including continuing deployment of AI agents across Operations
- With our go-to-market teams, including Sales, Success, Marketing, and Government Affairs, to ensure that our operations support new sales and customer retention goals
WHO YOU ARE
- Passionate about youth mental health and about partnering with schools to meet the mental health needs of students
- 10+ years healthcare operations experience in fast-paced environments, with venture-backed startup experience at growth stages strongly preferred
- Experience with meaningful P&L ownership
- Experience partnering with clinical teams and building multi-state clinical operations
- Experience managing or working closely with Revenue Cycle Management teams
- Proven experience managing large and dynamic teams, including managing people managers.
- Highly analytical, structured thinker with strong written and verbal communication skills
- Data-driven operator with strong technical skills. Highly proficient at defining metrics and getting the data you need to understand performance.
- Passionate about leveraging AI and automation to improve efficiency and quality of healthcare services
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 and benefits
- Meaningful equity ownership stake in Cartwheel
- Generous PPO medical, vision, dental and ortho coverage
- Unlimited/flexible PTO plus federal holidays
- Paid parental leave
- 401K with employer match
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 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