Overview Join Cartwheel to apply for the Director of Strategic Finance role at Cartwheel . Cartwheel is an early-stage company building a new kind of mental health program for kids with schools at the center. We collaborate with school staff to support kids, enabling earlier intervention, higher engagement in care, and better coordination among trusted adults in a student\'s life. We are backed by investors including Menlo Ventures, Reach Capital, General Catalyst, BoxGroup, and Able Partners. We seek mission-driven teammates to help make this vision a reality for millions of students across the country. 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 300 school districts in 15 states and expect to approach 1,000 districts across 30 states within two years. As Cartwheel\'s founding Director of Strategic Finance , you will 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. What you’ll do 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, working most closely with the People and Operations teams and engaging with Sales, Customer Success, R&D, and others. This includes creating analyses to inform key decisions (e.g., school district-level profitability, state-level contribution margin) Who you are 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 Compensation and benefits 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 to New Year\'s 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 are committed to equal employment opportunity regardless of race, color, religion, ancestry, national origin, gender, sexual orientation, disability status, or veteran status.

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