VP of Finance

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 federal funding for schools and the rise of telehealth, schools are reimagining what mental health support can look like. 

Cartwheel is an early-stage startup building technology-enabled mental health services that put schools at the center. We see our role as supporting on-campus counselors, psychologists, and school social workers who see kids every day. Instead of going around them, we collaborate with them. 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, Reach Capital, General Catalyst, BoxGroup, and Able Partners, and we're looking for mission-driven teammates to join our team.

ABOUT THE ROLE

Cartwheel is rapidly growing in scale and complexity. Our B2B2C business model includes contracts with school districts as well as medical billing revenue from health plans and patients who receive clinical services. Today, we work with more than 125 school districts in 9 states. Within 2 years, we’ll be in several hundred districts in 15-20 states, employing hundreds of team members across 3 legal entities (a Management Services Organization and two Professional Corporations).

As Cartwheel’s founding VP of Finance, you’ll build the finance function from the ground up and serve as a core member of the company’s leadership team enabling the company’s growth and success.

Role type: Full-time

Start date: Fall 2024

Location: Remote with quarterly in-person team retreats and co-locating as needed, especially as we get to know each other. Cartwheel’s headquarters are in Boston. 

WHAT YOU’LL DO

• Build the Finance function at Cartwheel from the ground up
• Improve and maintain Cartwheel’s financial/operating forecast, in close partnership with the COO, CEO, and leadership team. This includes scenario planning to drive investment decisions. 
• Own a rigorous annual planning & budgeting process, including monthly closes & financial reporting
• Monitor and report on key financial metrics aligned to our OKRs
• Conduct targeted analyses to inform strategic decisions (e.g., school district-level profitability, patient cohort analyses)
• Oversee accounting. Today, we work with a third party providing finance, accounting, and HR support – you’ll own this relationship and determine if/when to bring specific functions in-house. 
• Partner with the People team on decisions around things like employee compensation and benefits, stock options and cap table management, etc. 
• Partner with the sales and customer success teams on annual and quarterly revenue forecasting (new sales and renewals)
• Support our Series B fundraise in 2025, including maintaining key banking and investor relationships

WHO YOU ARE 

• You embody our values: Human, Humble, Accountable, Innovative, Resilient
• You thrive in a world of rapid growth and have been in a venture-backed, entrepreneurial environment
• You can seamlessly transition between strategic thinking and hands-on execution
• You have led finance in an organization with a similar go to market motion (B2B2C, state-by-state rollout) 
• You have meaningful experience in regulated industries (note: healthcare experience is NOT a must have). 
• You’re comfortable rolling up your sleeves to work with data, run analyses, and build models
• You have 8-10+ years in progressive finance roles with 4+ years as an operator and experience leading, developing, and growing a small team
• You have been the most senior finance leader on a team (e.g., Head/VP of Finance)

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: 

• Team-based culture with mission-driven colleagues who will go to bat for you
• Total cash compensation of $190,000 - $250,000/year
• Excellent health insurance
• Meaningful equity ownership stake
• Flexible paid time off
• Hybrid work environment with regular in-person team retreats
• 401K with employer match
• $500 annual educational stipend
• Macbook

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.