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.

• 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.

• Highlight your experience automating accounting processes for SaaS platforms—prepare a concise case study (1‑2 pages) showing how you reduced claim‑processing time or error rates using tools like NetSuite, Workday, or custom APIs, and be ready to walk interviewers through the metrics.
• Demonstrate familiarity with healthcare‑specific finance regulations (HIPAA‑related billing, ACA compliance, state licensure reimbursement rules). Include a brief portfolio slide of a compliance audit you led, noting any process improvements that saved the company money or reduced audit findings.
• Showcase remote‑team leadership: list the exact collaboration stack you use (e.g., Slack, Zoom, Asana, G‑Suite) and share a 5‑minute video or recorded demo of how you run weekly KPI reviews, cross‑functional syncs, and remote onboarding for new accountants.
• Prepare to discuss Headway’s mission impact: quantify how accounting decisions you’ve made previously improved provider cash flow or patient access (e.g., “implemented automated claim reconciliation that freed $2 M in provider reimbursements, enabling 5 % more patients to receive covered therapy”). Interviewers will look for this mission‑aligned financial stewardship.
• For salary negotiation, research recent remote senior finance salaries at health‑tech firms (e.g., BetterHelp, Talkspace) and bring a data‑backed range (e.g., $150‑$175 k base + equity). Tie your ask to the specific value you’ll add—such as scaling accounting systems to support 100 k additional providers within 12 months.