Head of Business Finance & Strategy

1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work—credentialing, claims, payment reconciliation—is a nightmare. Over 70,000 providers across all 50 states run their practice on our software, serving over 1 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale. We aren’t just a billing layer; we are becoming the platform where care actually happens.

As a Strategic Finance Manager, you will sit within the Strategic Finance GTM team and play a critical role in driving durable marketplace health across Provider and Patient. This role is highly cross‑functional and requires someone who thrives at the intersection of financial analysis and strategic decision‑making. You will build models, track performance, and surface insights that drive appointment volume, retention, and long‑run unit economics.

Serve as the primary Finance Business Partner for appointments reporting—patient churn, provider churn, appointments per provider, net revenue retention, and active patient behavior

Lead deep dives to identify business problems, perform root cause analysis, and develop strategies for accelerating progress—monitoring trends, surfacing early signals of de‑averaged performance, and partnering with product, operating, and growth teams to address issues and scale successful behaviors

Develop dashboards, reporting, and executive‑ready materials to communicate progress against goals

6+ years of professional experience, ideally in a mix of financial services (Investment Banking / Consulting / Private Equity) and highly analytical roles at a fast‑growing tech company (Strategic Finance)

Highly proficient in Google Sheets (advanced formulas) and Looker (or similar BI tools) and comfortable working with large datasets

Detail‑oriented with a “measure twice, cut once” approach when working with financial data

Excited about AI and how it’s reshaping finance, actively exploring and applying AI tools to drive faster insights, greater efficiency, and smarter decision‑making

Excited to work cross‑functionally with business teams to develop a greater understanding of function‑specific efficiency metrics and help course‑correct where necessary

Communicates complex insights clearly, tailoring the message for different audiences (finance vs. business/product partners)

In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

Equity compensation

Medical, Dental, and Vision coverage

Work‑from‑Home stipend

Therapy reimbursement

Fertility reimbursement and membership

13 paid holidays each year and a holiday break during the week between December 25th and December 31st

Flexible PTO

Employee Assistance Program (EAP)

Training and professional development

Inclusion and EEO Statement

Headway believes a team’s strength is in its people, and we are committed to the full inclusion of all qualified individuals. We ensure that persons with disabilities are provided with reasonable accommodations. We are an equal‑opportunity employer and do not discriminate on the basis of race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, or any other protected characteristic.

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