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 90,000 providers across all 50 states run their practice on our software, serving over 2.6 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, and building much of it with AI. 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 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
Comprehensive benefits:
Medical, dental, vision, HSA/FSA, 401(k) including match for 2027!, Carrot Fertility reimbursement, and paid parental, medical and caregiver leave.
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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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.
