Back to jobs
New

Director of Strategic Finance

Remote

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.

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. 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.

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. 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). 

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

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.

Create a Job Alert

Interested in building your career at Cartwheel? Get future opportunities sent straight to your email.

Apply for this job

*

indicates a required field

Resume/CV*

Accepted file types: pdf, doc, docx, txt, rtf

Cover Letter

Accepted file types: pdf, doc, docx, txt, rtf

Select...
Select...
Select...

How many years of experience do you have in corporate finance, FP&A, or strategic finance roles?

Voluntary Self-Identification

For government reporting purposes, we ask candidates to respond to the below self-identification survey. Completion of the form is entirely voluntary. Whatever your decision, it will not be considered in the hiring process or thereafter. Any information that you do provide will be recorded and maintained in a confidential file.

As set forth in Cartwheel’s Equal Employment Opportunity policy, we do not discriminate on the basis of any protected group status under any applicable law.

Select...
Select...
Race & Ethnicity Definitions

If you believe you belong to any of the categories of protected veterans listed below, please indicate by making the appropriate selection. As a government contractor subject to the Vietnam Era Veterans Readjustment Assistance Act (VEVRAA), we request this information in order to measure the effectiveness of the outreach and positive recruitment efforts we undertake pursuant to VEVRAA. Classification of protected categories is as follows:

A "disabled veteran" is one of the following: a veteran of the U.S. military, ground, naval or air service who is entitled to compensation (or who but for the receipt of military retired pay would be entitled to compensation) under laws administered by the Secretary of Veterans Affairs; or a person who was discharged or released from active duty because of a service-connected disability.

A "recently separated veteran" means any veteran during the three-year period beginning on the date of such veteran's discharge or release from active duty in the U.S. military, ground, naval, or air service.

An "active duty wartime or campaign badge veteran" means a veteran who served on active duty in the U.S. military, ground, naval or air service during a war, or in a campaign or expedition for which a campaign badge has been authorized under the laws administered by the Department of Defense.

An "Armed forces service medal veteran" means a veteran who, while serving on active duty in the U.S. military, ground, naval or air service, participated in a United States military operation for which an Armed Forces service medal was awarded pursuant to Executive Order 12985.

Select...

Voluntary Self-Identification of Disability

Form CC-305
Page 1 of 1
OMB Control Number 1250-0005
Expires 04/30/2026

Why are you being asked to complete this form?

We are a federal contractor or subcontractor. The law requires us to provide equal employment opportunity to qualified people with disabilities. We have a goal of having at least 7% of our workers as people with disabilities. The law says we must measure our progress towards this goal. To do this, we must ask applicants and employees if they have a disability or have ever had one. People can become disabled, so we need to ask this question at least every five years.

Completing this form is voluntary, and we hope that you will choose to do so. Your answer is confidential. No one who makes hiring decisions will see it. Your decision to complete the form and your answer will not harm you in any way. If you want to learn more about the law or this form, visit the U.S. Department of Labor’s Office of Federal Contract Compliance Programs (OFCCP) website at www.dol.gov/ofccp.

How do you know if you have a disability?

A disability is a condition that substantially limits one or more of your “major life activities.” If you have or have ever had such a condition, you are a person with a disability. Disabilities include, but are not limited to:

  • Alcohol or other substance use disorder (not currently using drugs illegally)
  • Autoimmune disorder, for example, lupus, fibromyalgia, rheumatoid arthritis, HIV/AIDS
  • Blind or low vision
  • Cancer (past or present)
  • Cardiovascular or heart disease
  • Celiac disease
  • Cerebral palsy
  • Deaf or serious difficulty hearing
  • Diabetes
  • Disfigurement, for example, disfigurement caused by burns, wounds, accidents, or congenital disorders
  • Epilepsy or other seizure disorder
  • Gastrointestinal disorders, for example, Crohn's Disease, irritable bowel syndrome
  • Intellectual or developmental disability
  • Mental health conditions, for example, depression, bipolar disorder, anxiety disorder, schizophrenia, PTSD
  • Missing limbs or partially missing limbs
  • Mobility impairment, benefiting from the use of a wheelchair, scooter, walker, leg brace(s) and/or other supports
  • Nervous system condition, for example, migraine headaches, Parkinson’s disease, multiple sclerosis (MS)
  • Neurodivergence, for example, attention-deficit/hyperactivity disorder (ADHD), autism spectrum disorder, dyslexia, dyspraxia, other learning disabilities
  • Partial or complete paralysis (any cause)
  • Pulmonary or respiratory conditions, for example, tuberculosis, asthma, emphysema
  • Short stature (dwarfism)
  • Traumatic brain injury
Select...

PUBLIC BURDEN STATEMENT: According to the Paperwork Reduction Act of 1995 no persons are required to respond to a collection of information unless such collection displays a valid OMB control number. This survey should take about 5 minutes to complete.