Head of IT & Security - Remote

JOB SUMMARYThe 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. Core Leadership ExpectationsThe IT Director will:Collaborate as Partners by building technology solutions alongside staff and leadership— communicating clearly, inviting input, and breaking down silos between IT and other departments.Supportive by Nature by providing responsive, patient IT guidance to staff at all skill levels — offering encouragement and structure rather than judgment.Remain Community-Centered by recognizing that the technology decisions made here directly impact the children and families served by CAA of OKC.Demonstrate Compassion in Action by meeting staff where they are, building confidence with technology rather than frustration, and treating every interaction as an opportunity to serve.Pursue Exceptional Quality through reliable systems, strong security practices, and IT support that genuinely raises the bar for what staff and families experience.Innovate with Purpose by identifying and implementing technology improvements that advance the Agency's mission — not for the sake of technology, but for the people it serves.DUTIES AND RESPONSIBILITIESTechnology Strategy & Infrastructure TransformationDevelop 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.Staff Support & Technology AdoptionProvide 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.Support onboarding processes by ensuring new staff are equipped and comfortable with Agency systems from day one.Network, Security & Systems ManagementDesign, 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.Operational Efficiency & Technology IntegrationSupport 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.Confidentiality & Ethical StandardsMaintain strict confidentiality of staff, client, and organizational data.Exercise sound professional judgment when addressing technology risks, vendor relationships, and organizational information.WORKING CONDITIONSThis position operates across a nonprofit office environment and multiple Head Start program sites. Work involves regular computer use, system troubleshooting, and staff-facing support. The IT Director should expect regular travel between Agency locations. Physical requirements include prolonged sitting and keyboard use, visual focus on computer monitors and technical equipment, ability to lift and carry equipment weighing up to 50 pounds, and work conducted in a climate-controlled office environment with regular local travel to Head Start sites and programlocationsSUPERVISIONReports to: Chief Operating OfficerDirectly Supervises: IT Assistants - team to be designed upon hire of DirectorCoordinates with: Central office staff and Head Start center staffQUALIFICATIONS REQUIREDProven 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.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.QUALIFICATIONS DESIREDExperience 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.

#J-18808-Ljbffr Community Action Agency Of Oklahoma