Odyssey Systems · 2 days ago
IT Director
Wakefield, MA
Full-time
Hybrid
Director/Executive
10+ years expOdyssey Systems is a world-class technical, engineering, and integration company serving the warfighting ecosystem. They are seeking an IT Director to lead the development of a modern IT department, drive digital transformation, and ensure compliance with cybersecurity standards.
ConsultingProject ManagementTechnical Support
No H1B
Security Clearance RequiredU.S. Citizen Only
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
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
Qualification
Required
Must be a US citizen
Secret clearance
Bachelor's degree in Information Technology, Computer Science, Cybersecurity, or a related field
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
Security+ (CompTIA)
Microsoft Certified: Azure Solutions Architect Expert
Microsoft 365 Certified: Enterprise Administrator Expert
Certified Ethical Hacker (CEH)
ITIL 4 Foundation or Intermediate
Certified CMMC Professional (CCP)
Preferred
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
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
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)
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
Strong background in ITIL practices and service desk operations
Experience with ticketing systems such as Zendesk, Jira Service Management, or ServiceNow
Skilled in managing vendor relationships, including contract negotiation and performance tracking
PMP or similar project management certification is a plus
Experience working in cleared environments or with DoD/Federal contracts
Familiarity with GFE (Government Furnished Equipment) lifecycle management
Strong relationship building skills
Benefits
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
Holidays
Company
Odyssey Systems
Odyssey Systems is a consultancy that offers acquisition, project management, medical research, technical support and training.
1001-5000 employees
Funding
Current Stage
Late StageLeadership Team
Matthew Kasberg
Chief Executive Officer
Bobby King
Vice President Operations
Recent News
Washington Technology
2025-10-28
Washington Technology
2025-09-16
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