Senior Strategic Finance Manager

As we scale towards $1B+ in revenue — connecting patients to mental healthcare and building the infrastructure that makes that possible at scale — Strategic Finance is one of the most operationally influential seats in the company. The decisions that shape how we grow, where we invest, and how we measure success run through this team. Strategic Finance exists at Headway to make better decisions regarding where to put the next dollar and then to make sure we actually execute against those decisions.

You'll be a true business partner to leaders across Product, Sales, Marketing, Operations, People, and other corporate functions — close enough to their work to understand what actually drives results, and rigorous enough to translate that into forecasts, unit economics, and business cases that hold up. You'll own core parts of our planning and forecasting rhythm, and you'll be the person leadership turns to when a decision needs a clear-eyed financial answer.

This is a highly cross-functional role for someone who thrives at the intersection of financial analysis and strategic decision-making. We're looking for someone who wants to influence outcomes, not just report on them.

You will:

• Partner with the business: Serve as an embedded finance business partner to 1-2 functions. You are responsible for translating business plans into financial plans and financial constraints into business tradeoffs.
  

• Drive capital allocation: Build and pressure-test business cases for investments — these could range across product bets, sales and marketing, market expansion, headcount, vendor, or build-vs-buy decisions. You’ll track outcomes and unit economics, closing the loop with leadership on what worked.
  

• Own planning & budgeting: Run the financial planning and monthly forecasting process end-to-end. Manage the operating budget with your partner teams — monthly reviews, variance analysis, and guidance.
  

• Maintain forecasts and KPIs: Own and continuously improve understanding of the drivers of your part of the business. Help the business define the KPIs that matter and then work with Data to make them visible and trusted.
  

• Bring AI into the workflow: Actively apply AI tools to drive faster insight, greater efficiency, and smarter decision-making — and help shape how the Finance team works as those tools evolve.

You'd be a great fit if:

• You're excited to join a mission-driven company and use your financial skills to help scale access to mental healthcare.
  

• You have 8+ years of experience, ideally blending Investment Banking, Consulting, or Private Equity/Venture Capital with a highly analytical Strategic Finance role at a fast-growing tech company.

• You've owned the numbers for a fast-growing business or product line — and you can point to decisions that went differently because of your work.
  

• You make the business better, not just the model. You don't just partner with the business — you shape its strategy. You lead cross-functional work without authority, earn trust through delivery, and translate financial analysis into decisions that change what the business does next.
  

• You bring structure to ambiguity. When the scope isn't defined, you define it. You proactively seek context, solve open-ended problems, and keep cross-functional groups moving with clarity even when the answer isn't settled.
  

• You communicate complex insights clearly. You tailor your message to the audience — finance vs. business partners — and make the takeaway impossible to miss.
  

• You see AI as a competitive advantage, not a feature to explore someday. You actively use AI tools to be more efficient, sharpen your analysis, and make smarter calls