Director of Strategic Finance

Join Cartwheel to help tackle the student mental health crisis

Cartwheel is an early-stage company building a new kind of mental health program for kids that puts schools at the center. We see our role as supporting school staff who see kids every single 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.

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 300 school districts in 15 states. Within 2 years, we’ll be approaching 1,000 school districts across 30 states.  

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

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

Role reports to: COO and Co-Founder

Start date: Fall 2025

Location: Preference for Boston area but open to remote with some travel to co-locate as we get to know each other.

• Build the Strategic 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. 
• Monitor and report on key financial metrics aligned to our OKRs to the Senior Leadership Team and Board of Directors. 
• Partner with departments to strategically manage their budgets and analyze variance
• Collaborate with outsourced accounting partners to ensure timely and accurate monthly close; work toward insourcing accounting function, including hiring a controller in early 2026
• Partner cross-functionally to drive effective decision-making across the business. You will be working most closely with the People and Operations teams but will also engage with Sales, Customer Success, R&D, and others as well. This includes creating important analyses to inform key decisions (e.g., school district-level profitability, state-level contribution margin). 

• You have led strategic finance functions in a business relevant to Cartwheel (e.g., B2B2C go to market motion, state-by-state market rollout, regulated industry) 
• You have relevant PE, banking, or consulting experience, including strong financial modeling skills
• You are a highly analytical thinker and enjoy working in a culture that values structured logical reasoning (for example, you naturally think in a MECE Framework)
• You are highly accountable (e.g., you define clear outcomes, set deadlines, escalate risks, deliver) 
• You are obsessive and will seek to understand our business down to the last dollar. You see this level of detail-orientation as core to your role and not something to delegate or outsource. 
• You embody our values: Human, Humble, Accountable, Innovative, Resilient

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
• Expected cash compensation of $175-225K based on relevant experience, plus a meaningful equity ownership stake
• 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
• Flexible and remote role with regular in-person retreats
• Annual learning stipend

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.