Odyssey Systems is seeking a skilled and dependable IT Systems Administrator 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.

The IT Systems Administrator maintains and supports the integrity of the operating system and cloud environment including the management, security, and optimization of the organization’s Microsoft 365 environment. This role ensures reliable operation of Microsoft cloud services including Exchange Online, SharePoint Online, Teams, OneDrive, Entra ID (Azure ID), and related security and compliance components. The administrator acquires, installs, and tests system software upgrades and computer components, configures software and resolves technical problems and maintains documentation of IT infrastructure and cloud environments as well as troubleshooting procedures. They will also work closely with IT leadership and cross-functional teams to enhance productivity, strengthen security posture, and support end-user needs.

This position is Hybrid on-site Tuesday - Thursday at our Wakefield, MA HQ (frequent visits to Lincoln, MA office)

Duties include, but not limited to: 

• Administer, configure, and maintain all Microsoft 365 services, including Exchange Online, SharePoint Online, Teams, OneDrive, Power Platform, and Entra ID.
• Manage user accounts, group policies, licensing, and permissions across the Microsoft 365 tenant.
• Monitor system performance, usage, and service health; troubleshoot issues and coordinate with Microsoft support as needed.
• Implement and maintain Microsoft 365 security configurations such as MFA, Conditional Access, identity governance, security baselines, and threat protection settings.
• Oversee data retention, eDiscovery, compliance policies, and backup/recovery procedures.
• Support and administer Microsoft Teams, including telephony/voice capabilities, collaboration policies, and lifecycle management.
• Manage Exchange Online components such as mail flow, transport rules, message tracing, and spam/phishing protections.
• Develop and maintain documentation for system configurations, procedures, and best practices.
• Provide Tier 2/3 support for end-user issues related to Microsoft 365 applications and services.
• Coordinate tenant-level changes, updates, and feature deployments.
• Work with cybersecurity teams to assess risks and ensure a secure configuration of the Microsoft 365 environment.
• Responsible for the maintenance, configuration, and reliable operation of computer systems, network servers.
• Install and upgrade computer components and software, manage virtual servers, and integrate automation processes.
• Troubleshoot hardware and software errors by running diagnostics, documenting problems and resolutions, prioritizing problems, and assessing impact of issues.
• Provide documentation and technical specifications to IT staff for planning and implementing new or upgrades of IT infrastructure.
• Lead desktop and helpdesk support efforts, making sure all desktop applications, workstations, and related equipment problems are resolved in a timely manner with limited disruptions.

Citizenship: Must be a US citizen

Minimum Required Qualifications

Education: Bachelor's Degree in a related field

Years of Experience: 7+

Certifications: Microsoft Certifications

Preferred Qualifications

Clearance: Secret

Education: Bachelor's Degree in a related field

Years of experience: 8+

Certifications: Microsoft Certifications

Technical Skills

• Strong knowledge of Entra ID (Azure AD), identity management, and cloud-based authentication.
• Experience with PowerShell scripting for automation and administration tasks.
• Understanding of Microsoft 365 security and compliance frameworks.
• Familiarity with Teams administration, including telephony/voice systems, is a plus.
• Knowledge of SharePoint Online architecture, permissions, and lifecycle management.
• Strong knowledge of systems and networking software, hardware, and networking protocols
• Experience with scripting and automation tools.
• Strong knowledge of implementing and effectively developing helpdesk and IT operations best practices, including expert knowledge of security, storage, data protection, and disaster recovery protocols.

Interpersonal Skills

• Strong troubleshooting and problem-solving skills.
• Excellent communication and documentation abilities.

Additional Information:

This position is Hybrid on-site Tuesday - Thursday at our Wakefield, MA HQ (frequent visits to Lincoln, MA office)

Travel: 0-10%

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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