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 accept insurance and scale their practice.
Headway was founded in 2019. Since then, we’ve grown into a diverse, national network of over 45,000 mental healthcare providers across all 50 states who run their practice on our software and have served over 1 million patients. We’re a Series D company with over $325m in funding from a16z (Andreessen Horowitz), Accel, GV (formerly Google Ventures), Spark Capital, Thrive Capital, Forerunner Ventures 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.
As Headway grows to fulfill our mission of making mental healthcare more accessible and affordable for everyone, we’re refining the foundational infrastructure to support a high-performing, secure, and scalable company with a remote workforce and offices in New York City, San Francisco and Seattle. We’re looking for a Director of IT to lead and scale our corporate IT function—owning everything from systems administration and help desk operations to endpoint management, SaaS tooling, and enterprise security practices.
In this role, you will define and drive the internal IT roadmap, ensuring our systems, tools, and support operations keep pace with our growth and regulatory requirements. You’ll lead a team responsible for delivering exceptional support to our hybrid workforce, maintaining secure and compliant systems, and implementing scalable, automated solutions to improve operational efficiency. This is a high-impact leadership role where you’ll partner closely with Security, People, Legal, Finance, and other stakeholders to ensure Headway’s corporate IT infrastructure is secure, efficient, and built to scale.
You’re a high-empathy, low-ego leader who thrives in building and enabling great teams. You lead with curiosity and humility, with a bias toward collaborationYou’re a tinkerer at heart, energized by technology, and excited to adapt and involve in order to enable innovation at scale. You’re someone who:
Brings a people-first approach to leadership, with a track record of cultivating high-trust, high-performance teams.
Leads with grit and humility, approaching even forgotten corners of the business with care and curiosity.
Has deep experience scaling internal IT functions within fast-growing mid-to-late stage startups, especially where technology ownership is distributed.
Takes pride in operational excellence—proactively building automated, scalable, and data-driven solutions to reduce manual effort and improve support.
Is fluent in infrastructure-as-code (e.g., Terraform), and has implemented configuration management systems at scale.
Is metrics- and automation-minded, with a desire to measure success and
continuously improve IT services.
Has explored and applied AI to modernize and scale IT operations (e.g., automating ticket triage, support workflows, or asset management).
Brings strong systems thinking to problems, while staying grounded and hands-on as needed.
After you apply to Headway, here are some details of what to expect during the interview process.
Salary information is based on a single salary target per role, and the starting salary for our Director, IT is $218,450.00 and increases to $257,000.00 based on industry tenure and experience
Benefits offered include:
* Equity Compensation
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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 employees work remotely across the US, with the option to work from offices in New York City, San Francisco and Seattle. Headway participates in E-Verify. To learn more, click here.