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. We've automated that.
But we're going further. Over 90,000 providers across all 50 states run their practice on our software, serving over 2.6 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, and building much of it with AI. We aren't just a billing layer; we are becoming the platform where care actually happens.
We're a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.
As we scale towards $1B+ in revenue — connecting patients to mental healthcare and building the infrastructure that makes that possible at scale — Strategic Finance is one of the most operationally influential seats in the company. The decisions that shape how we grow, where we invest, and how we measure success run through this team. Strategic Finance exists at Headway to make better decisions regarding where to put the next dollar and then to make sure we actually execute against those decisions.
You'll be a true business partner to leaders across Product, Sales, Marketing, Operations, People, and other corporate functions — close enough to their work to understand what actually drives results, and rigorous enough to translate that into forecasts, unit economics, and business cases that hold up. You'll own core parts of our planning and forecasting rhythm, and you'll be the person leadership turns to when a decision needs a clear-eyed financial answer.
This is a highly cross-functional role for someone who thrives at the intersection of financial analysis and strategic decision-making. We're looking for someone who wants to influence outcomes, not just report on them.
You will:
Partner with the business: Serve as an embedded finance business partner to 1-2 functions. You are responsible for translating business plans into financial plans and financial constraints into business tradeoffs.
Drive capital allocation: Build and pressure-test business cases for investments — these could range across product bets, sales and marketing, market expansion, headcount, vendor, or build-vs-buy decisions. You’ll track outcomes and unit economics, closing the loop with leadership on what worked.
Own planning & budgeting: Run the financial planning and monthly forecasting process end-to-end. Manage the operating budget with your partner teams — monthly reviews, variance analysis, and guidance.
Maintain forecasts and KPIs: Own and continuously improve understanding of the drivers of your part of the business. Help the business define the KPIs that matter and then work with Data to make them visible and trusted.
Bring AI into the workflow: Actively apply AI tools to drive faster insight, greater efficiency, and smarter decision-making — and help shape how the Finance team works as those tools evolve.
You'd be a great fit if:
You're excited to join a mission-driven company and use your financial skills to help scale access to mental healthcare.
You have 9+ years of experience, ideally blending Investment Banking, Consulting, or Private Equity/Venture Capital with a highly analytical Strategic Finance role at a fast-growing tech company.
You've owned the numbers for a fast-growing business or product line — and you can point to decisions that went differently because of your work.
You make the business better, not just the model. You don't just partner with the business — you shape its strategy. You lead cross-functional work without authority, earn trust through delivery, and translate financial analysis into decisions that change what the business does next.
You bring structure to ambiguity. When the scope isn't defined, you define it. You proactively seek context, solve open-ended problems, and keep cross-functional groups moving with clarity even when the answer isn't settled.
You communicate complex insights clearly. You tailor your message to the audience — finance vs. business partners — and make the takeaway impossible to miss.
You see AI as a competitive advantage, not a feature to explore someday. You actively use AI tools to be more efficient, sharpen your analysis, and make smarter calls
Medical, dental, vision, HSA/FSA, 401(k) including match for 2027!, Carrot Fertility reimbursement, and paid parental, medical and caregiver leave.
We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem – across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience. Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview.
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A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at https://headway.co/careers. Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @findheadway.com email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam.