Director of GTM Finance

Headway

23h•$169,000 - $265,000

About The Position

Headway is seeking a Director of GTM Finance to guide financial decision-making across its provider acquisition and patient acquisition growth engines. The role is responsible for capital deployment, evaluating returns on investment, and helping business leaders make informed growth decisions. The Director will own Headway’s end-to-end, driver-based revenue model, connecting providers, patients, funnel conversion, retention, and utilization to booked revenue. The role will facilitate capital allocation and unit economics analysis across provider and patient growth, including CAC, LTV, payback, and channel performance. It will also lead annual planning and monthly forecasting across GTM functions, including headcount, ramp, and capacity planning in partnership with business leadership. The Director will hire, coach, and develop a high-impact GTM Finance team; set analytical standards; define roles and DRIs; and build the function’s infrastructure, including models, dashboards, agentic workflows, and reporting in partnership with the Data team. The ideal candidate has owned forecasting and capital deployment for a growth business at meaningful scale, understands growth economics, builds trust with business leaders, actively uses AI tools to improve analysis and reporting, and brings structure to ambiguous situations.

Requirements

Experience owning the forecast and capital deployment for a growth business operating at meaningful scale.
Strong understanding of growth economics, including the ability to analyze individual channel payback and company-level capital allocation.
Experience building trust with business leadership and improving the quality of their decision-making.
Experience managing and growing teams, setting high standards, and coaching team members.
Active use of AI tools to accelerate analysis and reporting, improve scenario work, and reach insights faster.
Ability to bring structure to ambiguity, state assumptions clearly, revisit them as data arrives, and improve processes.

Responsibilities

Own Headway’s end-to-end revenue model, using a driver-based architecture that connects providers, patients, funnel conversion, retention, and utilization to booked revenue.
Facilitate capital allocation decisions across provider growth and patient growth through analysis of CAC, LTV, payback, and channel-level performance.
Run annual planning and monthly forecasting across GTM functions.
Own GTM headcount, ramp, and capacity planning in partnership with business leadership.
Hire, coach, and grow a high-impact GTM Finance team.
Set the team’s analytical bar, define roles and DRIs, and build its operating infrastructure, including models, dashboards, agentic workflows, and reporting alongside the Data team.
Help business leaders make informed growth and financial decisions.

Benefits

Equity compensation and meaningful ownership opportunities through equity
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 and a Holiday Break during the week between December 25th and December 31st
Flexible PTO
Employee Assistance Program (EAP)
Training and professional development
Robust health and wellness benefits
Retirement savings