About the Team & Role

At Headway, we're scaling quickly on our mission to transform mental health, and this hire will define how we administer equity today—and for years to come. You’ll own the end-to-end management and execution of our equity‑compensation program, partner deeply with People, Finance, Legal, Tax, Payroll and external counsel, and establish best‑in‑class processes, controls, and communications that keep our people—and our board—confident as we grow the company and function.

You Will: 

Architect and execute full‑cycle equity administration in Carta—including grant setup and issuance, vesting/exercise management, terminations/forfeitures, SOX‑compliant preparer/reviewer controls, cap‑table updates, and board‑approval packages. Lead vendor RFPs, evaluate and implement new platforms, and manage ongoing vendor relationships. Serve as the equity liaison for employees—design and deliver jargon‑free, enhanced communications, FAQs, and training; gather feedback to iterate materials; and ensure a seamless, employee‑facing experience. Partner cross‑functionally with Total Rewards (program design and evolution, grant issuance, enablement initiatives), Finance (expense reporting, forfeiture rates), Legal (agreements, policies, board material prep), Tax (withholding, corporate tax reporting), Payroll, and external counsel to maintain compliance, streamline hand‑offs, and produce regular equity‑plan reporting for executives and the board.

You’d Be a Great Fit If…

You have 6+ years of hands‑on equity administration experience at high‑growth or pre‑IPO companies, with deep expertise in Carta and primary equity vehicles (ISOs, RSAs, RSUs, ESPP). You’re a proactive, cross‑functional collaborator and clear communicator—adept at translating complex concepts into engaging, easy‑to‑understand materials. You’re passionate about leveraging cutting edge tools like AI and process automation, comfortable managing vendors and RFPs, and excited to build and scale a best‑in‑class equity function from the ground up. You hold a BA/BS in Accounting, Finance, Business Administration (or related), and you’re well‑versed in GAAP, SEC reporting, tax withholding, and SOX compliance.

Bonus Points:

Experience running an equity admin function and related change management through an IPO or other liquidity events Experience supporting system implementations and integrations

What We Offer:

A seat at the table—direct exposure to senior leadership and the board Opportunity to build and own a critical function in a rapidly scaling company Competitive salary, equity package, and comprehensive benefits A collaborative, mission‑driven culture focused on wellbeing and impact

Compensation and Benefits:

The expected base pay range for this position is $116,960 - $172,000, based on a variety of factors including qualifications, experience, and geographic location. 

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

Benefits offered include:

Equity Compensation Medical, Dental, and Vision coverage HSA / FSA 401K Work-from-Home Stipend Therapy Reimbursement 16-week parental leave for eligible employees Carrot Fertility annual reimbursement and membership 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st Flexible PTO Employee Assistance Program (EAP) Training and professional development