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 75000 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.

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.

• Manage and develop a team of four 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.

• 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 experience with Netsuite (and ideally Numeric and Ramp) and a bias toward using technology to scale accounting operations

• Strong communication and interpersonal skills with the ability to influence senior stakeholders and partner effectively across functions

• A proactive ownership mindset and the ability to thrive in a fast-paced ambiguous environment

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 participates in E-Verify. To learn more click here.

A notice to Headway applicants: To protect yourself against phishing and recruitment fraud please note that Headway only accepts applications through our official careers page at https://headway.co/careers. Headway will never refer you to external websites ask for payment or personal information or conduct interviews via messaging apps. All official communication will come from a @findheadway.com email address. If you are contacted by someone claiming to be from Headway via an unofficial channel please do not share any information and report it as spam.

What We Do

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 60000 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.

Why Work With Us

The demand for mental health care has never been higher underscoring the need for solutions like Headway that increase accessibility to clinical care. 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.

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