Director of IT

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. Were 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.