Odyssey Systems is seeking a skilled and dependable IT Support Specialist to provide end-user and systems support across multiple sites. This role will report directly to the Director of IT and will serve as a key IT resource supporting a growing organization of approximately 300 indirect and 1800 direct employees.

This position is ideal for a hands-on IT professional who combines strong technical troubleshooting ability with clear, confident communication — especially when supporting VIP stakeholders.

Duties include, but not limited to: 

End-User Support (Remote + Desk-side)

• Provide Tier 1 / Tier 2 support for Windows users in a hybrid environment.
• Troubleshoot and resolve issues across hardware, operating systems, SaaS applications, connectivity, and end user security.
• Provide professional, high-touch support to all user levels, including executives and other remote and hybrid users across the country.
• Support conference rooms and AV / meeting technology as needed.

Onboarding, Offboarding, and Provisioning

Own end-user onboarding/offboarding workflows including:

• Laptop provisioning
• Account creation / deprovisioning
• Software deployment
• Access requests and approvals
• Provision and manage users and access in Microsoft 365 and Entra ID
• Maintain documentation and ensure procedures are consistent and auditable.

Device Management & Endpoint Operations

Administer and support endpoint management systems including:

• Microsoft Intune
• NinjaOne
• Windows Autopilot
• Support endpoint security tooling such as Microsoft Defender and Bitdefender.
• Track, manage, and maintain endpoint inventory lifecycle (procurement, configuration, deployment, repairs, replacements).

ITSM & Documentation

• Work within ITSM ticketing systems to track, resolve, and document support activities.
• Create and maintain Knowledge Base (KB) documentation and user-facing guides.
• Contribute to continuous improvement of IT workflows and service delivery (ITSM).

Key Projects You’ll Contribute To

• User directory audit and access validation (M365)
• Endpoint inventory audit and lifecycle controls
• Creation and improvement of KB articles and internal IT documentation
• Supporting integrations or company expansion initiatives (including multi-site support)

Citizenship: Must be a US citizen

Minimum Required Qualifications

Clearance: N/A

Education: High School Diploma

Years of Experience: 5+

Certifications: A+, Network+

Preferred Qualifications

Clearance: N/A

Education: Bachelor's Degree

Years of experience: 5+

Certifications: Microsoft M365, Azure , ITIL

Technical Skills

• 5+ years of hands-on IT support experience (Tier 1/Tier 2)
• Experience supporting both Windows environments
• Strong experience with remote support tools and workflows
• Professional experience with Microsoft 365 administration and Entra ID
• Strong troubleshooting skills: able to isolate issues quickly and escalate appropriately

Nice-to-Have Qualifications

• Scripting or programming experience (PowerShell, Python, etc.)
• Experience conducting security audits, access reviews, and systems compliance checks

Interpersonal Skills

• Stong customer service skills
• Strong organizational skills
• Deliver consistent, reliable support outcomes
• Communicate clearly with stakeholders (especially VIP users)
• Proactively document systems and support procedures
• Contribute to measurable improvements in security, endpoint management, and user onboarding quality
• Be dependable and accurate — matching confidence with real capability

Additional Information

Hybrid on-site Tuesday - Thursday Wakefiled HQ (frequent visits to Lincoln office)

#LI-Mk1

Odyssey 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