Exceptional People + Purpose Beyond Profit = Watershed Outcomes

Exceptional People + Purpose Beyond Profit = Watershed Outcomes

Head of FP&A

Headway

Headway

Administration
San Francisco, CA, USA · New York, NY, USA
USD 210,120-309k / year + Equity
Posted on Aug 30, 2025

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 Headway’s Head of FP&A, you will build and manage a high-performing team overseeing all financial planning and analysis activities, operationalize KPIs to provide insight into business performance and develop best practices to ensure timely visibility into company performance. You will partner with cross-functional teams to understand performance, identify areas of opportunity, and support strategic decision-making. You will be a key player in driving coordination of strategic and financial planning processes as we scale. You will also serve as a trusted advisor and critical business partner to G&A functional leaders across the organization. This is an exciting opportunity for an experienced, detail-oriented leader who wants to make a significant impact on Headway’s growth and success.

You will:

  • Establish and drive company planning processes, ensuring resource allocation stays within budgets and forecasts are tightly linked to the company’s strategic goals
  • Oversee the company-wide operating model, ensuring key inputs are linked to company growth and profitability for use in annual planning/budgeting and monthly forecasting
  • Perform robust financial analysis on financial results and operating KPIs, identifying underlying trends and areas of opportunity
  • Design and deliver monthly/quarterly reporting packages that tell the story behind the numbers for the exec team and Board
  • Optimize systems to ensure automation of critical processes as we scale
  • Support competitive intelligence, M&A and other corporate development initiatives
  • Hire and develop a high-performing FP&A team to support the needs of the business
  • Drive capital allocation strategy, cash management, and expense governance
  • Support investor reporting, due diligence, and board-level discussions

You'd be a great fit if:

  • You have 10-15+ years of strategic finance/FP&A experience at a high-growth startup, ideally including 2+ years of consulting/banking/investing
  • You understand that people drive change, not spreadsheets, and are passionate about working with partners across all levels of the organization to steer progress
  • You have exceptional analytical skills with the ability to drill down into the weeds while maintaining a strategic lens
  • You have strong financial acumen and expertise in building financial models to support multiple business needs
  • You are a curious self-starter, resourceful and have a knack for problem-solving
  • You are a natural leader who enjoys hiring, mentoring and managing people to reach their highest potential
  • You’re energized by joining an early-stage startup and making immediate impact in a high-growth environment
  • You are an excellent communicator with strong interpersonal skills

Compensation and Benefits:

The expected base pay range for this position is $210,120 and increases to $309,000, based on a variety of factors including qualifications, experience, and geographic location.

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

#LI-LN1

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.

Headway employees work remotely across the US, with the option to work from offices in New York City, San Francisco and Seattle. Headway participates in E-Verify. To learn more, click here.