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.

Duties include, but not limited to: 

• 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.
• Strategic Technology Leadership
  • 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.
• Cybersecurity & Compliance Expertise
  • 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.
• Operational Efficiency
  • 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.
• Team Building & Talent Development
  • Leadership: Build and mentor a high-performing IT team with clear roles and responsibilities.
  • Culture: Foster a culture of accountability, innovation, and continuous improvement.
• Innovation & Future-Readiness
  • 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.
• Cost Control & Vendor Management
  • 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.

Citizenship: Must be a US citizen

Minimum Required Qualifications

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.

Preferred Qualifications

• 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

Why Join Us?

This is more than just a leadership role—it’s a chance to build something meaningful from the ground up. You’ll work alongside passionate professionals, shape the future of our IT capabilities, and make a lasting impact on national security and innovation.

Location: Wakefield, MA

Travel: 10%

Remote, Onsite, or Hybrid: Hybrid

#LI-MP1

Odyssey Systems is a world-class technical, engineering, and integration company serving the warfighting ecosystem with airborne integration, ISR, C2, and warfighter readiness capabilities. Odyssey meets the military’s operational needs by integrating layered defense systems from equipment, technology, and services to data, information, and business operations. We streamline defense acquisition and sustainment, engineering the technical battlefield with domain-specific proficiency to ensure lethality. Odyssey is dedicated to excellent contract execution, peak organizational performance, and fostering a workplace built on employee care.

Odyssey is proud to live out our core values of commitment, ambition, and respect in our work and communities through OdysseyCares, a philanthropic group focused on giving back through direct donations, an employer match program, and volunteering events.

Equal Opportunity Employer/Protected Veterans/Individuals with Disabilities

Final compensation for this position will be determined by various factors such as the Federal Government contract labor categories and contract wage rates, relevant work experience, specific skills and competencies, geographic location, education, and certifications.

This position is filled through continuous recruitment and will remain open until a sufficient pool of applications has been received.

Hired applicants may be eligible for benefits, including but not limited to, medical, dental, vision, life insurance, Tricare supplement, short-term disability, long-term disability, 401(k) match, flexible spending accounts, health savings accounts, employee assistance program, learning and development benefit, paid time off, and holidays.

Odyssey Benefits