Senior Manager, Accounting

1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that.

But we're going further. Over 75,000 providers across all 50 states run their practice on our software, serving over 1 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale. We aren't just a billing layer; we are becoming the platform where care actually happens.

We're a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.

ABOUT THE ROLE

As Headway's Senior Accounting Manager, you will lead day-to-day accounting operations and help establish scalable financial processes during a period of rapid growth. You'll manage a team of four accountants, owning month-end close, financial reporting, and technical accounting under US GAAP. This is a hands-on leadership role: you'll coach a high-performing team while partnering cross-functionally with Finance, People, Legal, Data, Product, and Engineering to ensure accurate and timely reporting. This role offers an opportunity to apply strong leadership, technical accounting expertise, and creative problem-solving to make a lasting impact on Headway's operations and audit readiness.

YOU WILL:

• Manage and develop a team of 3+ accountants — setting priorities, reviewing work, providing feedback, and coaching them on technical accounting and process improvements.

• Take a lead in automating accounting workflows using AI and LLMs (e.g., journal entry preparation, reconciliations, flux analysis, audit support), and lead the team in adopting these tools responsibly.

• Own the month-end, quarter-end, and year-end close process end-to-end, ensuring journal entries, reconciliations, accruals, and account analyses are accurate, complete, and delivered on schedule.

• Review and approve journal entries, balance sheet reconciliations, and flux analyses prepared by the team.

• Lead technical accounting research and policy setting under US GAAP, including documenting accounting positions and memos for complex transactions

• Support the annual audit by coordinating PBC requests and responses across the team, partnering with the Assistant Controller (who serves as the primary point of contact for external auditors.)

• Partner with the People team to oversee payroll accounting and reconciliations, and with cross-functional teams (Finance, Data, Engineering, Product) to scale accounting operations.

• Drive process improvements and automation initiatives across the accounting function, leveraging tools like Netsuite, Workday, and Ramp to reduce manual work and improve controls.

• Lead or sponsor strategic accounting projects, coordinating cross-functional partners and delivering measurable business impact.

YOU'D BE GREAT FOR THIS ROLE IF YOU HAVE:

• 10+ years of accounting and/or audit experience, including at least 5 years managing a team

• A Bachelor's degree in Accounting, Finance, or another relevant field (CPA preferred but not required)

• Strong working knowledge of US GAAP and experience leading month-end close in a high-growth environment

• Public accounting (Big 4 or large firm) and/or in-house experience at a high-growth or pre-IPO company

• History of utilizing LLM’s such as Claude to automate processes.

• A track record of coaching and developing accounting talent

• Hands-on expe