Director of IT Engineering

About the role

The Director of IT leads all IT operations at Charlie Health, including IT Service Delivery, IT Engineering, and IT Asset Management. This role is responsible for scaling a high-performing IT function that supports a distributed workforce and over 4,000 endpoints. This is a leadership role focused on execution, systems design, and operational excellence.

Responsibilities

• Lead IT Service Delivery, IT Engineering, and IT Asset Management with operating models aligned to ITIL and Agile
• Develop and execute an annual IT roadmap with quarterly OKRs aligned to business priorities
• Use data and service metrics to produce monthly business reports that track progress, improve performance and drive operational excellence
• Own core platforms including Atlassian, Google Workspace, Okta, Jamf, and Intune, and drive SaaS integrations
• Partner with Engineering on AWS, Azure, and GCP to ensure secure, scalable operations aligned with Zero Trust
• Define and execute an AI and automation roadmap to improve efficiency across IT and business workflows
• Ensure IT operations meet HIPAA and other compliance requirements and support audit readiness
• Lead IT delivery for office infrastructure including NYC build-out and ongoing multi-site operations across the US
• Own budget, vendor management, and cost optimization across IT systems and services

Requirements

• 10+ years of IT experience with at least 4 years in a leadership role
• Proven experience leading IT operations in a high-growth environment
• Deep expertise with Google Workspace, Okta, Atlassian (Jira, JSM, Confluence) and IT platforms
• Strong working knowledge of IT and Agile operating models such as Scrum or ITIL
• Demonstrated experience implementing process-based automation or AI-driven solutions in IT or business operations
• Experience managing cross-functional stakeholders and delivering large-scale initiatives
• Experience in healthcare or other regulated environments is nice to have
• Able to work a hybrid schedule of 4 days/week in our NYC office and located within 75 minutes' commuting distance of the office

Benefits

Charlie Health is pleased to offer comprehensive benefits to all full-time, exempt employees. Read more about our benefits here.