Director, GTM Finance

As Headway’s Director, GTM Finance, you will partner closely with the GTM leaders across our revenue-generating functions to support strategic decision-making and resource allocation decisions. You will mentor and manage a high performing team and collaborate with cross-functional stakeholders to derive insights and guide detailed financial analyses in order to build scalable models. Your leadership will have a significant impact on topics such as customer acquisition, monetization, market growth and expansion. This is an exciting opportunity for an experienced, data-driven leader who thrives in a fast-paced environment and wants to be a part of defining Headway’s growth and success.

You will: 

• 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

You'd be a great fit for the role if:

• 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

Compensation and Benefits:

The expected base pay range for this position is $174,760 - $257,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for performance-based variable compensation and 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

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