IT Director

COMMUNITY ACTION AGENCY OF OKLAHOMA•Oklahoma City, OK

2d•Hybrid

About The Position

The IT Director provides strategic and hands-on technology leadership for Community Action Agency of Oklahoma City. This role is responsible for overseeing all IT infrastructure, systems, and operations across the Agency's administrative office and Head Start program sites. The IT Director will have strong expertise in Windows Server environments, Microsoft 365 (Office 365) administration, and a solid networking background. This role is responsible for ensuring system reliability, security, scalability, and alignment with business needs.

Requirements

Proven experience as an IT Director, IT Manager, or Senior Systems Administrator.
Hands-on experience with Windows Server environments and Microsoft 365 administration.
Strong networking fundamentals — TCP/IP, routing, switching, firewalls, VPNs.
A genuine ability to explain technology to non-technical people without condescension or frustration.
Demonstrated patience and empathy when supporting staff at varying levels of technology comfort, including staff new to digital systems.
Ability to troubleshoot complex infrastructure and network issues.
Experience with security best practices and identity/access management.
Strong communication, organizational, and follow-through skills.
Comfort working in a resource-conscious nonprofit environment where prioritization and creativity matter.

Nice To Haves

Experience in a nonprofit, education, social services, or Head Start technology environment.
Familiarity with cloud migration projects and transitioning from on-premise to cloudbased infrastructure.
Experience with virtualization (Hyper-V, VMware).
Relevant certifications (Microsoft, Cisco, CompTIA, or equivalent).
Experience managing vendors, MSPs, and IT budgets.

Responsibilities

Develop and execute a phased IT roadmap aligned with the Agency's strategic plan, including migration to cloud-based servers and transition to a fully paperless operating environment.
Champion the Agency's shift to remote and hybrid work by ensuring infrastructure is not just available — but genuinely supported and optimized for all staff.
Manage and optimize Windows Server environments, including Active Directory, DNS, DHCP, Group Policy, and file/print services.
Administer and support Microsoft 365 services, including Exchange Online, SharePoint, OneDrive, Teams, and Entra ID (Azure AD).
Lead IT projects including system upgrades, cloud migrations, and new technology implementations across all Agency sites.
Provide hands-on, compassionate IT support to staff across multiple Head Start sites and administrative locations — meeting each person at their individual comfort level.
Develop and deliver accessible, jargon-free training for staff who may be using new systems for the first time, including older staff transitioning to digital tools.
Serve as a calm, approachable technology resource across all departments — building trust one interaction at a time.
Partner with program directors and department heads to understand their operational needs and translate them into workable technology solutions.
Support onboarding processes by ensuring new staff are equipped and comfortable with Agency systems from day one.
Design, implement, and maintain network infrastructure across all CAA locations, including LAN/WAN, VLANs, VPNs, firewalls, switches, and wireless networks.
Assist the Facilities Director in ensuring all locations have appropriate security systems and procedures; prioritize camera system upgrades based on security gaps, image quality, and storage capabilities.
Manage endpoint devices, patching, backups, disaster recovery, and business continuity planning.
Proactively monitor system performance, availability, and security — resolving issues before they become disruptions.
Ensure compliance with IT security best practices and identity/access management standards.
Support the Facilities team with the Agency's transition to electronic work order and inventory management systems, working to eliminate paper-based processes.
Evaluate, manage, and hold accountable vendors, MSPs, and technology contracts.
Maintain clear, thorough documentation for all systems, networks, and processes.
Manage the IT budget with nonprofit-minded stewardship, prioritizing high-impact investments.
Maintain strict confidentiality of staff, client, and organizational data.
Exercise sound professional judgment when addressing technology risks, vendor relationships, and organizational information.