Director of IT

Summary

Join Headway, a Series D company revolutionizing mental healthcare access, as their Director of IT. Lead and scale the corporate IT function, encompassing systems administration, help desk, endpoint management, SaaS tooling, and enterprise security. Define and drive the internal IT roadmap, ensuring systems and support operations align with growth and regulatory needs. Lead a team delivering exceptional support to a hybrid workforce, maintaining secure and compliant systems, and implementing scalable, automated solutions. Partner with cross-functional stakeholders to ensure Headway's IT infrastructure is secure, efficient, and scalable. This high-impact role requires strong leadership, technical expertise, and a passion for operational excellence.

Requirements

• 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

Responsibilities

• Define and drive the internal IT roadmap, ensuring our systems, tools, and support operations keep pace with our growth and regulatory requirements
• 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
• Partner closely with Security, People, Legal, Finance, and other stakeholders to ensure Headway’s corporate IT infrastructure is secure, efficient, and built to scale

Preferred Qualifications

Experience preparing for or operating within a public company environment, including IPO readiness and SOX compliance

Benefits

• 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