Director of IT

Salary: Location Type: Employment Type:

Position Overview

Headway's mission is to build a new mental health care system that everyone can access. We have developed technology that connects individuals with therapists through a software-enabled national network of providers who accept insurance. Recognizing that a significant portion of the US population struggles to afford mental healthcare due to providers not accepting insurance, Headway is creating a system that makes therapy accessible and affordable by simplifying the process for therapists to accept insurance and grow their practices.

Founded in 2019, Headway has rapidly grown into a diverse, national network of over 45,000 mental healthcare providers across all 50 states. Our software supports these providers, and we have served over 1 million patients. As a Series D company, we have secured over $325 million in funding from prominent investors including a16z (Andreessen Horowitz), Accel, GV (formerly Google Ventures), Spark Capital, Thrive Capital, Forerunner Ventures, and Health Care Service Corporation.

We are committed to making your time at Headway the most meaningful experience of your career. Join us and contribute to transforming mental healthcare for the better.

About the Role

As Headway expands to achieve its mission of making mental healthcare accessible and affordable, we are strengthening our foundational infrastructure to support a high-performing, secure, and scalable company with a distributed workforce and offices in New York City, San Francisco, and Seattle. We are seeking a Director of IT to lead and scale our corporate IT function. This role will encompass systems administration, help desk operations, endpoint management, SaaS tooling, and enterprise security practices.

In this leadership position, you will define and execute the internal IT roadmap, ensuring our systems, tools, and support operations align with our growth trajectory and regulatory requirements. You will manage a team dedicated to providing exceptional support to our hybrid workforce, maintaining secure and compliant systems, and implementing scalable, automated solutions to enhance operational efficiency. This is a high-impact role where you will collaborate closely with Security, People, Legal, Finance, and other stakeholders to ensure Headway's corporate IT infrastructure is secure, efficient, and built for 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 are a high-empathy, low-ego leader who excels at building and empowering great teams. You lead with curiosity and humility, prioritizing collaboration. You are a natural tinkerer, passionate about technology, and eager to adapt and evolve to enable innovation at scale. You possess the following qualities:

• A people-first approach to leadership, with a proven track record of cultivating high-trust, high-performance teams.
• Grit and humility, approaching all aspects of the business with care and curiosity.
• Deep experience scaling internal IT functions within fast-growing mid-to-late stage startups, particularly in environments where technology ownership is distributed.
• A commitment to operational excellence, proactively building automated, scalable, and data-driven solutions to minimize manual effort and improve support.
• Fluency in infrastructure-as-code (e.g., Terraform) and experience implementing configuration management systems at scale.
• A metrics- and automation-minded approach, focused on measuring success and continuously improving IT services.
• Experience exploring and applying AI to modernize and scale IT operations (e.g., automating ticket triage, support workflows, or asset management).
• Strong systems thinking capabilities, balanced with a hands-on approach when necessary.

What Will Make You Successful Here

• 6+ years of experience in C