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Payroll and HR Compliance Lead



Accounting & Finance, People & HR, Legal
Posted on Saturday, May 25, 2024

Headway’s mission is a big one - to build a new mental health care system everyone can access. We’ve built technology that helps people find great therapists with the first software-enabled national network of providers accepting insurance.

1 in 4 people in the US have a treatable mental health condition, but the majority of providers don’t accept insurance, making therapy too expensive for most people. Headway is building a new mental healthcare system that everyone can access by making it easy for therapists to take insurance and scale their practice.

Headway was founded in 2019 – since then, we’ve grown into a diverse, national network of over 30,000 mental healthcare providers across all 50 states who run their practice on our software. We’re a Series C company with over $225m in funding from a16z (Andreessen Horowitz), Accel, GV (formerly Google Ventures), Spark Capital, Thrive Capital, and Health Care Service Corporation.

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 Payroll and HR Compliance Lead, an early member of the People Ops function, you’ll play an integral role in supporting our 600+ employees & 400+ contingent workers across the US. We’re looking for a gritty, operational excellence and payroll and compliance obsessed team player to support Headway’s human hypergrowth to galvanize our progress towards our mission. This is an exceptional opportunity for someone interested in building a Payroll and HR Compliance function in a dynamic, high-growth and mission-driven environment.

You will:

  • Lead Headway's Payroll Processing e.g. build Headway’s payroll processing infrastructure for scale as well as lead efficient processing of commissions, bonuses, retro pay, LOAs, comp changes and severances using Workday and by partnering with our vendors
  • Own Headway’s HR Compliance e.g. fully manage Headway’s HR Compliance including States Correspondence, EEO Reporting, Unemployment Claims, Sanction Checks, Background Checks Monitoring, I9s Processes, Withholdings Monitoring, Immigration Visas Support, Audits Support, HR Trainings Monitoring, Handbook Signatures -- as well as HR Compliance automation, future state vision and its outsourcing services

You’d be a great fit if:

  • You have a minimum of 5-years of experience working on a People Team -- including experience working at a high growth technology start-up
  • You are extremely skillful and passionate about Payroll (preferred Certified Payroll Professional CPP) and HR Compliance
  • You have a high proficiency in Workday
  • You love to build new things optimizing for scale, efficiency and compliance

Compensation and Benefits:

  • Salary information is based on a single salary target per role and is differentiated based on geographic location (Group A, B, or C)
    • Group A: $130,000
    • Group B: $117,000
    • Group C: $104,000
  • Examples of cities located in each Compensation Grouping:
    • Group A = NYC, SF/Bay Area, LA Area, Seattle, Boston, Austin, and San Diego
    • Group B = Chicago, Miami, Denver, Washington DC, Philadelphia, Atlanta, Minneapolis, Nashville, Sacramento, Phoenix, and Portland
    • Group C = All remaining cities
  • 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

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 contact

Headway employees work remotely across the US, with the option to work from offices in New York City and San Francisco. Headway participates in E-Verify. To learn more, click here.