Own financial reporting, forecasting, and KPI visibility. Build and maintain core financial models and dashboards, lead budgeting and variance analysis, produce investor and board materials, and partner with department leaders to inform operational decisions.
Join Cartwheel to help tackle the student mental health crisis!
ABOUT THE ROLE
WHAT YOU'LL DO
WHO YOU ARE
WHY YOU’LL LOVE CARTWHEEL
We participate in E-Verify. Please be prepared to provide acceptable documentation to verify your identity and work authorization
Cartwheel uses AI-assisted tools to support our hiring process. This may include tools that help organize and surface applications for recruiter review, AI-powered candidate communications and scheduling, interview recording and documentation, and an AI chat tool available to candidates during the process. All hiring decisions are made by Cartwheel recruiters and hiring managers. No candidate is selected or eliminated from consideration solely by an automated system. All hiring decisions are made by humans. If you have questions about how AI is used in our process or would like to request an alternative review method, please contact [email protected]
Note: Please do not contact our Care, Provider, or Patient Services lines regarding job postings or application status. These teams support our patients and families and are not involved in the hiring process. For all recruitment-related questions, please email [email protected].
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 A Street Ventures, 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
We're hiring a Strategic Finance Associate to own financial reporting, planning, and KPI/OKR visibility across the organization. This is a net-new role — and a real opportunity to build something. Right now, our financial and operational metrics live in different systems, most reporting is backward-looking, and department leaders don't yet have the structured financial partnership they need to make confident decisions.
Reporting to Sam Bilow, VP Finance, you'll consolidate our reporting infrastructure, build forward-looking forecasts, and become a trusted cross-functional partner to leaders across Care Ops, Clinical, Product, Engineering, and beyond. This role is for someone who has done the analytical work — not just supported it. If you've built models from scratch, pressure-tested assumptions with stakeholders, and had your work actually change a decision, we want to talk.
Role type: W2, Full-Time, Salaried position
Salary range: $90,000 - $140,000 plus meaningful equity options
Location: Remote
WHAT YOU'LL DO
Strategic Finance
- Build forward-looking forecasts to support runway planning and board communication
- Identify opportunities to automate and scale financial reporting processes
- Conduct ad-hoc analyses that help leadership make faster, better-informed decisions
Financial Modeling & Reporting
- Maintain and improve Cartwheel's core financial model — P&L, cash burn, scenario modeling
- Own monthly board slide deck, investor reporting, and SLT financial updates
- Maintain and continuously improve KPI dashboards
Budgeting & Planning
- Lead the annual budgeting cycle: templates, department kick-offs, reviews, and final consolidation
- Partner with department heads on budget planning and resource allocation
- Maintain budget vs. actual tracking and variance analysis
WHO YOU ARE
- You have 2–4 years of experience in strategy consulting (MBB, boutique strategy, or similar) or investment banking, startup or high-growth experience is a strong plus
- You build models from first principles. You can explain why you chose the drivers you did, what assumptions you pressure-tested, and what changed because of what you found
- You connect finance to operations naturally. You think about how a business actually works, not just how it reports
- You communicate clearly to non-financial audiences — you know when to simplify and when precision matters
- You're self-directed and ownership-oriented: you spot problems, propose solutions, and don't wait to be asked
- You've operated in ambiguous environments — you forecast with 80% information, create frameworks where none exist, and don't wait for a clean dataset
- You care about the mission. You understand that finance is in service of student mental health, not the other way around
What will make you stand out: We set a high bar for this role. We’re looking for folks with the demonstrated ability to reason through unfamiliar business models quickly. We're building a sustainable clinical model around historically underserved populations, and the finance function needs to reflect that complexity.
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
- Generous PPO medical, vision, and dental/ortho coverage
- Life Insurance
- Generous paid time off, including company closure from Christmas-New Years (12/25-1/1)
- Paid holidays and sick leave
- 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
- Laptop
We participate in E-Verify. Please be prepared to provide acceptable documentation to verify your identity and work authorization
Cartwheel uses AI-assisted tools to support our hiring process. This may include tools that help organize and surface applications for recruiter review, AI-powered candidate communications and scheduling, interview recording and documentation, and an AI chat tool available to candidates during the process. All hiring decisions are made by Cartwheel recruiters and hiring managers. No candidate is selected or eliminated from consideration solely by an automated system. All hiring decisions are made by humans. If you have questions about how AI is used in our process or would like to request an alternative review method, please contact [email protected]
Note: Please do not contact our Care, Provider, or Patient Services lines regarding job postings or application status. These teams support our patients and families and are not involved in the hiring process. For all recruitment-related questions, please email [email protected].
Cartwheel Cambridge, Massachusetts, USA Office
700 Massachusetts Ave, 3rd Floor, Cambridge, Massachusetts , United States, 02139
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