Senior Manager, Accounting

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