Director, Information Technology

Care Access

5h•Remote

About The Position

The Director of Information Technology leads IT operations and infrastructure in a fast-paced healthcare environment. This hands-on leadership role is responsible for managing a team of 8-10 FTEs and overseeing outsourced support resources while also serving as a technical resource for complex initiatives. The Director brings deep expertise in Microsoft 365 environments, identity management, and cloud platforms, along with a track record of driving operational excellence and leveraging emerging technologies, including AI. This role owns IT budgeting, procurement, and vendor relationships while ensuring service delivery excellence across the organization. This position blends strategic program leadership (60%) with hands-on technical execution (40%). The Director will develop roadmaps, allocate resources, and ensure alignment with business priorities while remaining actively engaged in technical problem-solving and infrastructure decisions.

Requirements

Proven leadership of IT operations at enterprise scale. Ability to set strategy, drive execution, and deliver measurable outcomes.
Strong experience administering and optimizing Microsoft 365 environments.
Experience managing mixed Windows and Mac endpoint environments.
Working knowledge of identity and access management platforms, specifically Okta and Microsoft Entra.
Familiarity with Azure or AWS cloud platforms, with the ability to oversee cloud infrastructure and make strategic decisions.
Demonstrated experience with AI technologies, whether through organizational rollouts, internal support enablement, or automation initiatives.
Experience in healthcare or a related regulated industry.
Proven ability to manage IT budgets and negotiate with vendors.
Experience managing outsourced support resources and third-party service providers.
Strong communication skills with the ability to partner effectively across all levels of an organization.
15+ years of experience in information technology or related fields.
7-8+ years of management experience leading technical teams, including people leadership and program ownership.
Bachelor's degree in Computer Science, Information Technology, or related field, or equivalent experience.

Nice To Haves

AWS or Azure certifications preferred but not required.
Call center or contact center technology experience.
Experience supporting distributed or fully remote workforces.

Responsibilities

Lead and develop a high-performing IT team of 8-10 FTEs while managing relationships with outsourced support providers. Set objectives, provide coaching, and conduct performance management.
Oversee IT operations across a mixed Windows and Mac environment within a Microsoft 365 ecosystem. Ensure system reliability, performance, and user satisfaction.
Manage identity and access management using Okta and Microsoft Entra. Ensure secure, efficient provisioning and access controls across the organization.
Drive AI initiatives including rollout planning, internal support enablement, and automation opportunities. Evaluate and implement AI tools to improve operational efficiency.
Own IT budgeting, procurement, and vendor negotiations. Manage vendor relationships, contracts, and cost optimization while meeting operational objectives.
Serve as a technical escalation point and hands-on contributor for complex infrastructure, cloud, and operational challenges.
Ensure service delivery excellence for end-user support, including oversight of help desk operations and service level management.
Partner with stakeholders across the organization to align IT services with business needs and priorities.
Develop and maintain IT policies, procedures, and documentation.
Evaluate and implement new technologies to improve efficiency and support organizational growth
Maintain a current IT roadmap aligned to business priorities and technology trends.
Coordinate with Security, Legal, and Compliance on regulatory obligations and technology requirements.
Champion IT best practices and provide training and guidance to end users.