IT Engineer, People Systems (Workday) at Headway | Powderkeg

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.

Reporting to our IT Engineer Manager, you’ll play a pivotal role in building and maturing an IT function that applies the best solutions to the opportunities and complexities of a 3-sided marketplace and dynamic business model. This work enables us to make mental healthcare more accessible and affordable to patients across the US, and makes it easy for mental healthcare providers to accept patients with insurance to grow their practice, provide care, and make money.

You will:

  • Utilize your subject matter expertise as the lead for Workday at Headway.
  • Partner closely with peers and stakeholders across the entire organization to enable workflow and technology efficiencies during a period of high growth at Headway.
  • Participate in an on-call rotation with other IT team members to provide technical support to Headway workers by reading/listening, researching and then answering questions and troubleshooting issues.
  • Develop and maintain quantitative reporting methods to increase visibility and enable our teams to make data-informed decisions.

You will love this role if…

  • You are motivated by seeing the impact of your work on the success of other teams.
  • You have experience taking on projects from vision to reality in partnership with cross-functional teams and third-party products and consultants.
  • You love deeply understanding operational workflows and enjoy creating elegant solutions to complicated problems.
  • You love making the right tradeoff between speed and scalability in order to best empower the teams you work with
  • You are energized by working in a fast-paced startup environment.

You’d be a great fit if...

  • You have 5+ years of experience working as a Workday Administrator.
  • You have administration expertise with at least two of the following products (Okta, Google Workspace, Zoom, Slack, Atlassian Jira, Atlassian Confluence, CultureAmp, Checkr, Lessonly, 1Password)
  • You have experience or a strong desire to learn to build automation with
  • You are skilled at working with stakeholders to collect, synthesize, and present solutions that meet business needs and drive workflow efficiency.
  • You are an excellent project manager who is organized and methodical, and takes the time to deliver high-quality work.
  • You are a team player with no ego, welcome feedback with a growth mindset, and are adept at managing up and across teams.

Compensation and Benefits:

  • Salary information is based on a single salary target per role:

    • The salary for IT Engineer, People Systems is $146,625.
  • 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
    • Unlimited 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.

Job Summary
  • Job Title
    IT Engineer, People Systems (Workday)
  • Company
  • Location
  • Employment Type
    Full time
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