Strategic Finance Lead, GTM

Headway’s mission is to build a new mental healthcare system accessible to everyone. We automate insurance-related administrative tasks and serve over 1 million patients across 50 states through our software platform.

About the role

We are seeking a Strategic Finance Lead, GTM to join our team. This role requires a blend of financial analysis and strategic decision-making, focusing on capital deployment and GTM investments.

Responsibilities

• Build and maintain financial models to assess GTM investment efficiency
• Scenario planning and evaluating trade-offs across growth initiatives
• Own budgeting and forecasting processes for GTM spend
• Analyze operating KPIs and funnel data to evaluate unit economics, channel performance, and overall GTM effectiveness
• Partner cross-functionally to surface insights and support strategic decision-making
• Develop dashboards, reporting, and executive-ready materials to communicate progress against goals

Requirements

• 4+ years of professional experience, ideally in a mix of financial services and highly analytical roles at a fast-growing company
• Proficiency in Google Sheets (advanced formulas) and Looker (or similar BI tools)
• Detail-oriented and detail-focused when working with financial data
• Excited to work cross-functionally with the business teams to develop function-specific efficiency metrics and help course-correct where necessary
• Proactive, resourceful, and a self-starter who anticipates stakeholder needs
• Excited about AI and its role in reshaping finance, actively exploring and applying AI tools to drive faster insights, greater efficiency, and smarter decision-making
• Communicate complex insights clearly, tailoring messages for different audiences (finance vs. marketing)
• Thrives in a fast-paced, cross-functional environment and enjoys collaborating with marketing, finance, and growth teams
• Excited about joining a mission-driven company and driving marketing efficiency to improve mental healthcare access

Benefits

• Compensation Range: $131,750 - $165,000
• 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