Director of GTM Finance

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.

Headway is deploying hundreds of millions in capital across two growth engines — provider acquisition and patient acquisition. On the one hand, the two engines are economically distinct — different funnels, different metrics, different payback profiles. On the other hand, there are deeply interrelated components between the motions that (1) make the Headway marketplace work and (2) drive our ability to build a better mental healthcare system that everyone can access.

We're looking for a Director of GTM Finance to drive our financial decision making for these two growth engines. You're responsible for capital deployment, evaluating our return on investment, and helping our business leaders make good growth decisions. Ultimately your work is a critical enabler to helping providers find Headway and patients find high quality care.

• The revenue model and forecast. Own Headway's revenue model end to end – the driver-based architecture connecting providers, patients, funnel conversion, retention, and utilization to booked revenue.

• Capital allocation and unit economics. Facilitate smart capital allocation decisions across provider growth and patient growth, through deep understanding of CAC, LTV, payback, and channel level performance.

• Planning and capacity. Run annual planning and monthly forecasting across GTM functions. You own GTM headcount, ramp, and capacity planning in partner with business leadership.

• Team and function building. Hire, coach, and grow a high-impact GTM Finance team. Set the analytical bar, define roles and DRIs, and build the infrastructure the function runs on – models, dashboards, agentic workflows, and reporting alongside the Data team.

• You've owned the forecast and capital deployment for a growth business operating at meaningful scale.

• You know growth economics cold, and you're obsessed with what's underneath the average. You move fluidly between a single channel's payback curve and the company-level view of where capital should go, building trust in business leadership on financial decision making. You make business leaders better at deciding, not just better at reporting.

• You lead a team you'd want to work for. You've managed and grown teams, you set a high bar and coach to it, and you're genuinely energized by developing people.

• You see AI as a competitive advantage for finance, not a feature to explore someday. You actively use AI tools to compress analysis and reporting cycles, sharpen scenario work, and get to insight faster — and you bring that orientation to how you build the function around you.

• You bring structure to ambiguity — fast. You set a defensible assumption, name it as an assumption, revisit it when the data comes in, and leave every process more rigorous than you found it.

Compensation and Benefits:

The expected base pay range for this position is $169,000-$265,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:

  • Equity compensation

  • Medical, Dental, and Vision coverage

  • HSA / FSA

  • 401K

  • Work-from-Home Stipend

  • Therapy Reimbursement

  • 16-week parental leave for eligible employees

  • Carrot Fertility annual reimbursement and membership

  • 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st

  • Flexible PTO

  • Employee Assistance Program (EAP)

  • Training and professional development

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.

Headway participates in E-Verify. To learn more, click here.

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.