Senior Manager, Accounting

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Headway

WebsiteLinkedInAll Job Openings

501 - 1000 employees

Founded 2019

🏥 Healthcare

🏪 Marketplace

☁️ SaaS

💰 $100M Series D - Headway on 2024-07

Healthcare • Marketplace • SaaS

Headway is a healthcare technology company (Therapymatch, Inc. ) that operates an insurance-native marketplace connecting people with licensed mental health providers — therapists and psychiatrists — for in-person and online care. Headway matches users with providers by specialty, location, and insurance coverage, handles insurance verification and billing, and offers tools for providers (provider portal and an insurance-native EHR) to reduce administrative burden. The platform partners with 100+ insurance plans, supports many languages, and emphasizes affordable, in-network mental health care.

📋 Description

• 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.

🏖️ Benefits

• robust health and wellness benefits • retirement savings • meaningful ownership opportunities through equity