Role Description The Executive Director of Information Technology is the senior technology leader for a company of approximately 150 employees, supported by a three-person internal IT team and selected external service providers. This is a working, player-coach leadership role responsible for practical technology strategy, cybersecurity, reliable operations, project delivery, vendor performance, and cost control. The position combines executive-level judgment with sufficient hands-on technical experience to guide Microsoft environments, networking, endpoint services, and complex escalations. As a largely remote organization, Team Housing Solutions depends on secure, reliable technology to support a geographically dispersed workforce. The Executive Director of Information Technology will establish and maintain the technology infrastructure, cybersecurity controls, and collaboration environment necessary to enable employees to work securely and effectively from any approved location while protecting company and customer information. Key Responsibilities - Leadership, Strategy and Business Partnership - Develop and maintain a practical IT strategy, annual operating plan, and prioritized technology roadmap aligned with company growth, customer commitments, and available resources. - Advise the executive team on technology investments, cybersecurity risk, compliance readiness, operational resilience, and business opportunities. - Prepare and manage the IT budget, staffing plan, forecasts, contracts, and capital requests; identify savings and control recurring technology costs. - Establish clear priorities, policies, service expectations, and concise performance reporting appropriate for a small IT organization. - Lead cross-functional technology projects, including scope, schedule, budget, risk, communications, vendor coordination, adoption, and results. - Cybersecurity and CMMC Readiness - Own the company cybersecurity program and maintain a risk-based security posture for both government and private-sector operations. - Lead CMMC Level 2 and NIST SP 800-171 readiness, including governance of the System Security Plan, POA&Ms, evidence, policies, assessments, and protection of Controlled Unclassified Information. - Coordinate with qualified consultants, assessors, MSPs, and internal business owners when specialized compliance or security expertise is required. - Ensure effective controls for identity and access, MFA, endpoints, email, networking, backups, remote access, vulnerability management, security awareness, and incident response. - Communicate material security risks, incidents, remediation needs, and business impacts to executive leadership. - Technology Operations and Hands-On Leadership - Oversee secure and reliable operation of Microsoft 365, Entra ID, SharePoint, Teams, Windows endpoints, device management, networking, telecommunications, cloud services, and key business applications. - Provide hands-on technical direction and escalation support when needed, while avoiding unnecessary dependence on the Executive Director for routine administration. - Ensure effective onboarding, offboarding, identity and access management, endpoint provisioning, patching, asset management, documentation, backup and recovery, and comprehensive support for a geographically dispersed remote workforce. - Maintain practical disaster recovery and business continuity capabilities for critical technology services. - Evaluate and implement technology improvements that measurably improve security, service, productivity, or cost. - Team, Vendor and Service Management - Lead and develop the three-person IT team; define roles, priorities, accountability, cross-training, and professional development. - Manage MSPs, consultants, software providers, telecommunications vendors, and other partners through clear scopes, service levels, costs, and performance expectations. - Negotiate and manage licensing, renewals, contracts, and technology purchases; eliminate unnecessary tools and duplicate services. - Maintain a responsive, customer-focused support model with appropriate escalation, documentation, and measurable improvement. - Build productive relationships with executives, department leaders, employees, customers, auditors, and government-program stakeholders. Qualifications - Bachelor's degree in technology, business, or a related field, or an equivalent combination of education and relevant experience. - Approximately 10 years of progressive IT experience, including meaningful responsibility for an IT function, team, or broad technology portfolio. - Leadership experience covering strategy, budgeting, staffing, projects, vendors, cybersecurity, operations, and executive communication in a small or midsize organization. - Practical Microsoft experience, including Microsoft 365, Entra ID, SharePoint, Teams, Windows endpoints, identity, security, and device management. - Solid working knowledge of networking, cloud services, endpoint security, backup and recovery, remote-work technology, and common business applications. - Experience managing MSPs, consultants, contracts, licensing, renewals, and technology cost optimization. - Experience with CMMC, NIST SP 800-171, government contracting cybersecurity, or a comparable regulated environment. - Ability to move comfortably between executive discussions, project leadership, staff coaching, vendor management, and occasional hands-on technical problem-solving. Preferred Qualifications - Experience supporting both government contract and private-sector business operations. - Experience in housing, lodging, hospitality, logistics, facilities, construction, or another distributed service organization. - Experience with ERP implementations, systems integration, business process improvement, or technology-enabled services. - One relevant professional certification is helpful but not required, such as a Microsoft, cybersecurity, CMMC, project-management, or IT service-management certification.