Director of IT, Headway
$218.4-257k
+ Equity
Therapist-by-insurance marketplace
Be an early applicant
Therapist-by-insurance marketplace
1001+ employees
Be an early applicant
$218.4-257k
+ Equity
1001+ employees
Company mission
To build a new mental healthcare system, rewired for access and affordability.
Role
Who you are
- 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
- 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
- 6+ years of experience in Corporate IT, including 3+ years leading and scaling IT teams in fast-paced, high-growth environments
- Demonstrated success building internal IT systems, infrastructure, and support functions from the ground up—ideally in hybrid or remote-first organizations
- Strong experience with tools such as Okta, MDMs (e.g., Jamf, Intune), Google Workspace, Slack, Atlassian, and ITSM platforms
- Proficiency in infrastructure-as-code practices, especially Terraform, and a strong foundation in configuration management and automation
- Understanding of security and compliance frameworks such as SOC2, HIPAA, or HITRUST
- Passion for delivering great internal support—balancing speed, scale, and user empathy with a focus on service and performance metrics
- Comfort working cross-functionally with leaders in Security, People, Legal, and Finance to align IT with business priorities
- Familiarity with how AI is being leveraged in IT operations today and interest in applying it to drive support efficiency and scale
- Bonus: Experience preparing for or operating within a public company environment, including IPO readiness and SOX compliance
What the job involves
- 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
Application process
- Initial screen: You’ll connect with someone in recruiting so you can learn more about the team, Headway’s mission and exciting growth, and we can get a better idea of your background
- First round: You'll meet with the Hiring Manager to go deeper into your technical and people leadership experiences
- Mid round: You’ll meet several more team members for one technical and multiple behavioral interviews, leaving you with a fuller picture of what it’s like to work at Headway
- Final round: You'll meet with our CTO for a final interview and an opportunity to learn more about the larger opportunity to have an impact on our team
- References and the Offer: Our favorite part of the process! We'll send over all of the details, including specifics on employee equity, and congratulatory messages from excited future team members!
Our take
1 in 4 US citizens are currently living with treatable mental health conditions, however, a vast majority of people are unable to access the care they need, the primary reason being cost. Headway connects clients with therapists who accept insurance as payment and provides independent practitioners with the tools and resources needed to serve their patients and manage administrative workloads.
Headway’s concept is timely, with national mental health under particular strain following events from the past few years. The company facilitates over 300,000 appointments per month and has attracted backing from the likes of Accel and Google Ventures.
Covering 16 states and the District of Columbia, the company intends to broaden its presence across the US using its 2023 Series C funding of $125 million. This is a crucial avenue for further growth, as medical care deserts across the US mean the potential market is vast.
Freddie
Company Specialist at Welcome to the Jungle
Insights
64% employee growth in 12 months
Company
Funding (last 2 of 6 rounds)
Jul 2024
$100m
LATE VC
Oct 2023
$125m
SERIES C
Total funding: $327m
Company benefits
- Work from home opportunities
Company HQ
Tribeca, New York, NY
Leadership
Andrew Adams
(CEO)Worked as a Product Analyst at Spring, and was a Software Development Engineer Intern at Amazon.
Salary benchmarks
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