Senior Manager, Accounting

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.

Responsibilities

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

Requirements

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

Nice to have

CPA preferred but not required; Ideally Numeric and Ramp