Executive Director Information Technology

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., 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

• 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., * 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.

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