Director of IT

About the role:

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.

Tools we use

• Business Applications: Atlassian (Jira, Confluence), Google Workspace, Zoom, Slack, 1Password
• Endpoints: MacOS, Chrome, Jamf, InTune, Kolide
• Identity and Access Management: Okta, Lumos
• Ticketing: Jira Service Desk, ZenDesk, Jira Projects
• Office Technology: Cisco Meraki, Verkada

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. 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.

What will make you successful here

• 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.

Our interview process

After you apply to Headway, here are some details of what to expect during the interview 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!

Compensation and Benefits:

• 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
  • 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

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