Closes in 14 days Remote Job

Benefits Lead

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 25,000 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.

Join us, and make an impact.

As Headway’s Benefits Lead, you’ll play an integral role in defining the benefits strategy for our 500+ employees across the US as the first benefits team member.

Reporting to our Head of Total Rewards, you’ll have direct exposure to all benefits strategy and administration in this high-visibility role. You will be pivotal in shaping and executing benefits strategy, overseeing administration processes, managing leave of absence programs, ensuring compliance with regulations, and effectively communicating benefits information to our employees.

This is an exceptional opportunity for someone interested in owning benefits administration with setting long-term benefits strategy in a dynamic, high-growth and mission-driven environment.

You will own:

Benefits Strategy:

  • Develop and implement a strategic benefits plan aligned with organizational goals

  • Conduct market research to stay current with industry trends and best practices

  • Collaborate with senior leadership to align benefits programs with employee needs

Benefits Administration:

  • Oversee the day-to-day administration of all employee benefits programs

  • Coordinate with external vendors and ensure seamless benefits delivery

  • Resolve employee inquiries related to benefits and provide guidance on utilization

Leave of Absence Management:

  • Manage all aspects of leave administration, including FMLA, disability, and other statutory leaves

  • Work closely with HRBPs and managers to ensure compliance with leave policies

  • Provide support and guidance to employees throughout the leave process

Benefits Program Compliance:

  • Stay up-to-date on federal, state, and local regulations impacting benefits

  • Conduct regular audits to ensure benefits programs comply with legal requirements

  • Collaborate with legal and compliance teams to address any issues and implement necessary changes

Program Documentation:

  • Maintain accurate and up-to-date benefits-related documentation

  • Develop and update employee benefits handbooks and materials

  • Ensure all documentation is in compliance with regulatory standards


  • Design and execute effective communication strategies for benefits programs

  • Conduct regular employee education sessions on available benefits

  • Serve as a point of contact for benefits-related inquiries and concerns

You’d be a great fit if:

  • 4-6 years in benefits administration and strategy

  • Experience in a high-growth start-up environment is a plus

  • In-depth knowledge of federal and state regulations related to employee benefits and leave policies

  • Strong analytical and problem-solving skills

  • Excellent communication and interpersonal skills

  • Ability to collaborate with cross-functional teams

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

      • 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.

Don't wait, tomorrow could be too late.