Director, GTM Finance

Summary

Join Headway as the Director, GTM Finance, and partner with revenue-generating teams to drive strategic decision-making and resource allocation. Mentor and manage a high-performing team, collaborating with cross-functional stakeholders to build scalable financial models. Your leadership will significantly impact customer acquisition, monetization, market growth, and expansion. This role requires 10-15+ years of experience in operational roles at high-growth tech companies, including GTM, strategic finance, FP&A, strategy, or management consulting. You will be responsible for detailed financial analyses, developing presentations, and driving operational excellence. Headway offers a competitive compensation package and comprehensive benefits.

Requirements

• You have 10-15+ years of experience in operational roles at high-growth tech companies, including background in GTM, strategic finance, FP&A, strategy or management consulting
• You’re excited to work cross functionally with the business teams to develop a greater understanding of function-specific financial metrics and help course-correct where necessary
• You are a collaborator that proactively partners across teams while holding them accountable for results
• You have a passion for and experience with leading high-performing teams and managing people; you are excited about coaching team members and creating space for learning and development
• You seek an environment that fosters individual growth through open-feedback and high-autonomy
• You are extremely detail oriented and love building models and systems that scale
• You are an excellent communicator with strong interpersonal skills

Responsibilities

• Partner closely with Marketing, Sales, Partnerships, Customer Experience, Revenue Strategy and Product teams to track KPIs and support financial analyses and decision-making
• Conduct detailed analyses into performance trends to address any implications to team strategies and the company-wide model
• Manage, develop and mentor a high-performing GTM finance team
• Lead the development of presentations to track and convey progress on specific initiatives
• Drive operational excellence and best practices by supporting development of GTM team operating models and help drive ongoing budgeting and forecasting

Benefits

• 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