[All remote jobs](https://jobicy.com/jobs.md)[![Headway.co logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2021/12/068391a61855fb604bca051cafe3c510.jpeg)](https://jobicy.com/company/headway.md)[Headway.co](https://jobicy.com/company/headway.md) # Senior Manager, Accounting Review the role, location requirements, compensation details, and application process before deciding whether this opportunity fits your next career move. [Apply for this job](#job-application)[View company](https://jobicy.com/company/headway.md)ShareRemote from[USA](https://jobicy.com/job-region/usa.md)SalaryUSD 163,200–204k / yrDepartment[Finance & Accounting](https://jobicy.com/categories/accounting-finance.md)EmploymentFull TimeExperienceSeniorPublished1 Nov 2026Apply before1 Dec 2026Listing views40Application actions4Application toolkit ## Make your next move. Prepare your resume, explore your fit, and draft a cover letter for this opportunity. AI Summary ## The role, at a glance. Headway is seeking a Senior Accounting Manager to lead day-to-day accounting operations in a high-growth mental-health technology company. The role manages a team of accountants and owns the month-end, quarter-end, and year-end close processes, financial reporting, reconciliations, and audit support. It requires deep US GAAP expertise, technical accounting judgment, and experience building scalable processes and controls. The manager will partner broadly with Finance, People, Legal, Data, Product, and Engineering while driving automation through NetSuite, Workday, Ramp, AI, and LLM tools. This is a hands-on leadership position for an experienced accounting professional who can coach a team and operate effectively amid ambiguity and rapid change. ## Role DNA A quick view of the complexity, pace, ownership and collaboration implied by the job description. ### Job Complexity 5/5EasyHard ### Pace & Pressure 5/5RelaxedFast-paced ### Autonomy Level 5/5GuidedFull ownership ### Communication Load 5/5IndependentCollaborative AI insightThis senior role combines people leadership, ownership of close and audit readiness, technical US GAAP research, and cross-functional operational scaling. The fast-growth environment and mandate to automate accounting workflows require strong independent judgment and change-management capability. ## Salary analysis Estimated compensation compared with the broader US market for similar roles. Estimated job median (per year)Market rate$183,600US market range (per year)$160k–$220k0$242.00k AI insightHeadway discloses an annual base salary range of $163,200 to $204,000 USD, with a midpoint of $183,600. This is a credible and competitive range for a US-based senior accounting management role requiring extensive leadership, close ownership, US GAAP expertise, and high-growth company experience. The estimated US market range is $160,000 to $220,000 annually. ## Core skills Skills and capabilities most closely associated with this opportunity. [US GAAP](https://jobicy.com/jobs?search_keywords=US%20GAAP.md)[Technical accounting](https://jobicy.com/jobs?search_keywords=Technical%20accounting.md)[Month-end close](https://jobicy.com/jobs?search_keywords=Month-end%20close.md)[Financial reporting](https://jobicy.com/jobs?search_keywords=Financial%20reporting.md)[Audit support](https://jobicy.com/jobs?search_keywords=Audit%20support.md)[Accounting automation](https://jobicy.com/jobs?search_keywords=Accounting%20automation.md)[NetSuite](https://jobicy.com/jobs?search_keywords=NetSuite.md)[Workday](https://jobicy.com/jobs?search_keywords=Workday.md)[Ramp](https://jobicy.com/jobs?search_keywords=Ramp.md)[Payroll accounting](https://jobicy.com/jobs?search_keywords=Payroll%20accounting.md)[Balance sheet reconciliations](https://jobicy.com/jobs?search_keywords=Balance%20sheet%20reconciliations.md)[Team leadership](https://jobicy.com/jobs?search_keywords=Team%20leadership.md)[Process improvement](https://jobicy.com/jobs?search_keywords=Process%20improvement.md)[LLM automation](https://jobicy.com/jobs?search_keywords=LLM%20automation.md)[Cross-functional collaboration](https://jobicy.com/jobs?search_keywords=Cross-functional%20collaboration.md) Sample interview questionsHow have you improved the month-end close process while maintaining accuracy and strong controls?I begin by mapping the close calendar, identifying manual bottlenecks and control risks, and assigning clear owners for each deliverable. I standardize reconciliations and journal-entry support, automate repeatable workflows where appropriate, and use close metrics to reduce cycle time without weakening review procedures. Describe your approach to researching and documenting a complex US GAAP accounting conclusion. I define the transaction facts, identify the relevant authoritative guidance, assess viable accounting alternatives, and document the conclusion in a clear memo. I include the technical analysis, assumptions, financial-statement impact, stakeholder input, and required disclosures so the position is auditable and consistently applied. What experience do you have managing and developing an accounting team? I set clear priorities and quality standards, provide timely review feedback, and create development plans tied to each person’s technical and leadership goals. I balance coaching with accountability by giving team members ownership of meaningful work while remaining available to resolve complex issues and remove obstacles. How would you use AI or LLMs responsibly in an accounting organization? I would focus first on repeatable, low-risk tasks such as drafting journal-entry support, organizing reconciliation evidence, summarizing flux drivers, and preparing audit-request trackers. Each output would remain subject to documented human review, access controls, data-security requirements, and validation against source systems before it affects books or reporting. How do you partner effectively with teams such as People, Legal, Data, Product, and Engineering? I establish shared objectives, translate accounting requirements into practical operational needs, and communicate risks early rather than at the end of a process. I use regular working sessions, documented decisions, and measurable milestones to align partners on system changes, payroll matters, contract implications, and reporting requirements. Opportunity details ## About this role. 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. Headway participates in E-Verify. To learn more, click [here.](https://www.e-verify.gov/sites/default/files/everify/posters/EVerifyParticipationPoster.pdf) 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](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](http://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. 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