Cartwheel is hiring a Strategic Finance Associate to build financial reporting, forecasting, budgeting and KPI infrastructure for a growing healthcare technology company focused on improving student mental health. The fully remote, full-time role offers $90,000–$140,000 plus meaningful equity options.
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About Cartwheel
Cartwheel is an early-stage company developing a new approach to children’s mental health care by putting schools at the center of its model.
The company works alongside school staff to support earlier intervention, improve student and family engagement, and strengthen coordination between the trusted adults involved in a student’s care.
Cartwheel is backed by investors including A Street Ventures, Menlo Ventures, Reach Capital, General Catalyst, BoxGroup and Able Partners.
The company is looking for mission-driven professionals who want to contribute to improving mental health outcomes for students across the United States.
Role Overview
Cartwheel is creating a new Strategic Finance Associate position to strengthen its financial planning, reporting and business intelligence capabilities.
Job Title: Strategic Finance Associate
Company: Cartwheel
Job Location: Remote, United States
Employment Type: Full-time
Contract: W2, Salaried
Salary: $90,000–$140,000 + meaningful equity options
Work Arrangement: Remote
Reporting to the VP Finance, Sam Bilow, the successful candidate will help consolidate financial and operational reporting systems, develop forward-looking forecasts and provide financial insights to leaders across Care Operations, Clinical, Product, Engineering and other departments.
This is an opportunity for someone who wants to build financial infrastructure rather than simply maintain existing processes.
The role is particularly suited to candidates who have experience building financial models, challenging assumptions, conducting strategic analysis and influencing business decisions through data.
Key Responsibilities
Strategic Finance
The Strategic Finance Associate will:
- Build forward-looking financial forecasts to support runway planning and board communications.
- Identify opportunities to automate and scale financial reporting.
- Conduct ad-hoc financial and business analyses.
- Provide insights that help leadership make faster and better-informed decisions.
- Connect financial performance with operational drivers across the business.
Financial Modeling and Reporting
Responsibilities include:
- Maintain and improve Cartwheel’s core financial model.
- Work across P&L, cash burn and scenario modeling.
- Own the monthly board slide deck.
- Prepare investor reporting and senior leadership financial updates.
- Maintain and continuously improve KPI dashboards.
- Consolidate financial and operational metrics from different systems.
Budgeting and Planning
The successful candidate will:
- Lead the annual budgeting cycle.
- Develop budgeting templates and coordinate department kick-offs.
- Work with department leaders throughout the budgeting and review process.
- Consolidate departmental budgets.
- Partner with leaders on resource allocation.
- Maintain budget-versus-actual reporting.
- Conduct variance analysis and identify key financial drivers.
Required Experience and Qualifications
Cartwheel is looking for candidates who have:
- 2–4 years of experience in strategy consulting, investment banking or a similar analytical environment.
- Experience in a startup or high-growth company is strongly preferred.
- Demonstrated ability to build financial models from first principles.
- Strong understanding of financial drivers and business assumptions.
- Experience pressure-testing assumptions and translating findings into recommendations.
- Ability to connect financial analysis with operational performance.
- Strong communication skills and the ability to explain financial concepts to non-financial stakeholders.
- Excellent problem-solving and analytical abilities.
- A self-directed approach with strong ownership and initiative.
- Comfort working with incomplete information and ambiguity.
- An interest in Cartwheel’s mission of improving student mental health.
What Will Make You Stand Out?
Cartwheel has a high bar for this position and is seeking someone who can quickly understand unfamiliar business models and identify the financial and operational drivers that matter.
Strong candidates will be comfortable:
- Building analytical frameworks where none exist.
- Forecasting with incomplete information.
- Challenging assumptions constructively.
- Turning complex financial data into practical recommendations.
- Working cross-functionally with senior leaders.
- Operating in a rapidly changing startup environment.
Experience helping build financial functions or reporting infrastructure at a high-growth company can be particularly valuable.
Why Join Cartwheel?
The Strategic Finance Associate will have the opportunity to work at the intersection of finance, healthcare, technology and social impact.
The role offers substantial ownership within a growing organization, allowing the successful candidate to help establish processes and systems that will shape how Cartwheel makes financial and strategic decisions as it scales.
Benefits Include
- Competitive compensation
- $90,000–$140,000 salary
- Meaningful equity ownership
- Generous PPO medical, vision and dental/orthodontic coverage
- Life insurance
- Generous paid time off
- Company closure from December 25 through January 1
- Paid holidays and sick leave
- Paid parental leave
- 401(k) with employer match
- Flexible remote work
- Regular in-person retreats
- Annual learning stipend
- Company laptop
Work Arrangement
This is a fully remote position based in the United States.
The position is:
- Full-time
- W2
- Salaried
- Remote
- Eligible for regular in-person company retreats
Applicants should also be prepared to provide acceptable documentation to verify identity and work authorization because Cartwheel participates in E-Verify.
Diversity and Inclusion
Cartwheel is committed to creating an inclusive workplace that welcomes diverse backgrounds, perspectives and experiences.
The company is an equal opportunity employer and states that employment decisions are made without discrimination based on factors including race, color, religion, ancestry, national origin, gender, sexual orientation, disability or veteran status.
How to Apply
Candidates interested in the Strategic Finance Associate opportunity should apply through Cartwheel’s recruitment process.
For recruitment-related questions, candidates should contact talent@cartwheelcare.org. Cartwheel asks applicants not to contact its Care, Provider or Patient Services teams regarding job applications.
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