Strategic Finance Lead, GTM at Headway

This role is ideal for a finance professional with 4+ years of experience who bridges the gap between high-level investment banking/private equity rigor and the

Work type: remote

Location: Remote

Salary: $131,750 – $160,000/yr

Type: Full-time

Summary

This role is ideal for a finance professional with 4+ years of experience who bridges the gap between high-level investment banking/private equity rigor and the fast-paced operations of a high-growth startup. You should be a master of Google Sheets and Looker, comfortable navigating large datasets to determine if capital spent on patient and provider growth is actually delivering ROI. The position offers a strong remote-first culture with geographic-based salary ranges up to $155k, plus equity in a Series D unicorn backed by top-tier VCs like a16z and Accel. Beyond the mission-driven work, the benefits package is standout, featuring a week-long December holiday break, therapy reimbursement, and 16 weeks of parental leave. **You might be a good fit if you...** * Have a background in Strategic Finance, PE, or Consulting and want to own the GTM funnel. * Are a "measure twice, cut once" analyst who thrives on data integrity and complex modeling. * Enjoy cross-functional collaboration, specifically translating financial insights for Marketing and Growth teams. * Want to work at the intersection of healthcare accessibility and data-driven unit economics.

Job Description

Headway’s mission is a big one – to build a new mental health care system everyone can access. We’ve built technology that helps people find great therapists with the first software-enabled national network of providers accepting insurance.

1 in 4 people in the US have a treatable mental health condition, but the majority of providers don’t accept insurance, making therapy too expensive for most people. Headway is building a new mental healthcare system that everyone can access by making it easy for therapists to accept insurance and scale their practice.

Headway was founded in 2019. Since then, we’ve grown into a diverse, national network of over 60,000 mental healthcare providers across all 50 states who run their practice on our software and have served over 1 million patients. We’re a Series D company with over $325m in funding from a16z (Andreessen Horowitz), Accel, GV (formerly Google Ventures), Spark Capital, Thrive Capital, Forerunner Ventures and Health Care Service Corporation.

We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.

As a Strategic Finance Lead, GTM, you will sit within the Strategic Finance team and play a critical role in ensuring capital is deployed efficiently across Provider and Patient Growth initiatives. This is a highly cross-functional role for someone who thrives at the intersection of financial analysis and strategic decision-making. You'll build models, track performance, and surface insights that guide how we allocate resources and scale our GTM investments.

You Will

• Build and maintain financial models to assess GTM investment efficiency, scenario plan, and evaluate trade-offs across growth initiatives

• Own budgeting and forecasting processes for GTM spend, partnering with budget owners to align plans with strategic priorities.

• 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

• You have 4+ years of professional experience, ideally in a mix of financial services (Consulting / Equity Research / Private Equity) and highly analytical roles at a fast-growing company (Strategic Finance)

• You are highly proficient in Google Sheets (advanced formulas) and Looker (or similar BI tools) and comfortable working with large datasets

• You are detail-oriented and have a “measure twice, cut once” approach when working with financial data

• You’re excited to work cross functionally with the business teams to develop a greater understanding of function-specific efficiency metrics and help course-correct where necessary

• You take ownership and are a resourceful self-starter—you proactively seek context, solve ambiguous problems, and anticipate stakeholder needs

• You are excited about AI and how it's reshaping finance, and you actively explore and apply AI tools to drive faster insights, greater efficiency, and smarter decision-making

• You communicate complex insights clearly, tailoring your message for different audiences (finance vs. marketing)

• You thrive in a fast-paced, cross-functional environment and enjoy collaborating with marketing, finance, and growth teams

• You are excited about joining a mission-driven company and driving marketing efficiency to improve mental healthcare access

The expected base pay range for this position is $131,750 - $160,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for 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

We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem – across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience. Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview.

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