IT Director

Odyssey Systems Consulting Group•Wakefield, MA

4d•Hybrid

About The Position

We’re seeking a dynamic and forward-thinking IT Director to lead the development of a modern, secure, and scalable internal IT department. This is a high-impact leadership role responsible for aligning technology strategy with business goals, driving digital transformation, and ensuring compliance with CMMC Level 2/3 standards. You’ll play a central role in building a high-performing team, implementing AI-enabled efficiencies, and modernizing our infrastructure to support both internal operations and Department of Defense (DoD) contract requirements. This is an exciting opportunity for a hands-on leader who thrives in fast-paced, mission-driven environments.

Requirements

Citizenship: Must be a US citizen
Clearance : Secret
Education: Bachelor’s degree in Information Technology, Computer Science, Cybersecurity, or a related field. Master’s-level coursework or progress toward an MBA or technical graduate degree is highly valued.
Years of Experience: 10+ years of progressive IT operations experience
5+ years in a leadership role within a $250M–$1B defense or government contracting environment
Proven success with CMMC/NIST compliance, Microsoft 365 migrations, and enterprise system integrations
Certifications: Security+ (CompTIA) Often a baseline requirement for DoD 8570 compliance; useful for team members and leaders alike.
Microsoft Certified: Azure Solutions Architect Expert Demonstrates deep expertise in designing and implementing Azure-based solutions.
Microsoft 365 Certified: Enterprise Administrator Expert Validates skills in managing Microsoft 365 services, including identity, security, compliance, and supporting technologies.
Certified Ethical Hacker (CEH) Useful for roles with a strong cybersecurity and threat detection component.
ITIL 4 Foundation or Intermediate Helps with IT service management and aligning IT services with business needs.
Certified CMMC Professional (CCP) Especially relevant for this role, as it directly supports CMMC readiness and audit preparation.

Nice To Haves

Leadership & Communication Proven ability to lead cross-functional teams in high-stakes environments
Strong interpersonal and communication skills, with the ability to translate technical concepts for non-technical stakeholders
Experience mentoring and developing IT professionals at various career stages
Cybersecurity & Compliance Deep understanding of CMMC Level 2/3, NIST 800-171, and DFARS requirements
Experience leading successful cybersecurity audits and remediation efforts
Familiarity with zero-trust architecture and endpoint detection/response (EDR) tools
Cloud & Infrastructure Hands-on experience with Microsoft Azure, Microsoft 365, and hybrid cloud environments
Expertise in M365 tenant management, Exchange Online, SharePoint, and Teams
Familiarity with infrastructure-as-code (IaC) and automation tools (e.g., Terraform, Ansible)
AI & Automation Exposure to AI/ML tools and platforms, including chatbot integration and predictive analytics
Experience with workflow automation using Power Automate, Logic Apps, or similar tools
IT Service Management Strong background in ITIL practices and service desk operations
Experience with ticketing systems such as Zendesk, Jira Service Management, or ServiceNow
Vendor & Project Management Skilled in managing vendor relationships, including contract negotiation and performance tracking
PMP or similar project management certification is a plus
Security Clearance & Government Contracting Experience working in cleared environments or with DoD/Federal contracts
Familiarity with GFE (Government Furnished Equipment) lifecycle management
Interpersonal Skills Strong relationship building skills

Responsibilities

Shape the IT Vision Develop and execute a 1–3 year strategic roadmap that supports business growth, enhances user experience, and integrates emerging technologies like AI chatbots and predictive analytics.
Lead CMMC Compliance Own and drive all aspects of CMMC Level 2/3 readiness. Lead internal audits, resolve PIN login gaps, and ensure continuous improvement in cybersecurity and compliance practices.
Drive Operational Excellence Oversee enterprise IT operations, including Microsoft 365 administration for 230+ indirect users and GFE management for 1,500+ direct users. Lead initiatives to reduce the Zendesk backlog by 50% and improve service delivery metrics.
Build and Inspire a High-Performing Team Recruit, mentor, and lead a growing IT team. Future direct reports include: Cybersecurity Lead M365/Cloud Team Lead Network/Infrastructure Team Lead Innovation Specialist Helpdesk Technicians and Analysts
Champion Innovation and Vendor Management Pilot AI/ML tools, continuously improve internal systems (e.g., intranet), and manage vendor relationships, including MSAs and SOWs.
Vision & Roadmap Development: You'll define and execute a 1–3 year IT strategy aligned with business goals and DoD contract requirements.
Digital Transformation: Lead initiatives that modernize infrastructure, integrate AI tools, and automate workflows to improve efficiency and scalability.
CMMC Level 2/3 Readiness: Ensure the organization meets and maintains compliance with federal cybersecurity standards, reducing risk and enabling contract eligibility.
Audit Preparedness: Lead internal and external audits, proactively identifying and closing security gaps.
Infrastructure Oversight: Manage enterprise systems like Microsoft 365, Azure, and GFE for thousands of users, ensuring uptime, performance, and cost control.
Process Improvement: Streamline IT operations, reduce ticket backlogs, and implement service-level improvements that enhance user experience.
Leadership: Build and mentor a high-performing IT team with clear roles and responsibilities.
Culture: Foster a culture of accountability, innovation, and continuous improvement.
AI & Automation: Pilot and implement AI/ML tools that improve decision-making, reduce manual work, and support data-driven operations.
Scalability: Design systems and processes that can grow with the business, supporting future acquisitions, contracts, and workforce expansion.
Budget Awareness: Track and manage software, hardware, and service costs to avoid waste and ensure ROI.
Vendor Oversight: Negotiate and manage MSAs and SOWs to ensure vendor performance aligns with business needs.