Location: Chicago, IL
Salary: $65.00 USD Hourly - $80.00 USD Hourly
Description: IT Service Desk LeadLocation and Work ArrangementArlington, VirginiaOnsite, five days per weekRole OverviewWe are seeking an experienced, hands-on
IT Service Desk Lead to lead day-to-day service desk operations while serving as a senior technical resource across a secure Microsoft government cloud environment.
This is a player-coach role for an IT professional who enjoys developing people, improving service delivery, and personally tackling complex technical challenges. Reporting to the IT Manager, you will lead a team of IT professionals while helping strengthen internal capabilities, enhance end-user support, and maintain technology operations within a regulated federal contracting environment.
You will play a key role in supporting Microsoft 365 GCC High, Azure Government, identity and device management, compliance initiatives, and ongoing operational excellence efforts.
What You'll DoService Desk Leadership & Operations- Lead daily IT service desk operations, providing coaching, direction, and accountability to team members.
- Oversee Tier 1 through Tier 3 support activities, ensuring incidents and requests are prioritized, assigned, escalated, and resolved effectively.
- Manage ticket queues and workload distribution to drive timely resolution and outstanding customer service.
- Take ownership of complex technical issues that require deeper investigation and hands-on troubleshooting.
- Build and maintain a service-focused culture centered on responsiveness, accountability, and continuous improvement.
- Develop and refine service desk processes, workflows, documentation, and escalation procedures.
- Analyze recurring issues and service trends to improve support quality, reduce resolution times, and enhance the end-user experience.
Microsoft 365 GCC High & Azure Government Administration- Serve as a senior technical resource across Microsoft 365 GCC High, Azure Government, Microsoft Entra ID, Intune, Defender, Exchange, Teams, SharePoint, and related Microsoft technologies.
- Administer user accounts, access permissions, devices, applications, and core Microsoft cloud services.
- Manage end-user computing operations, including device deployment, imaging, configuration, troubleshooting, and lifecycle management.
- Build, administer, and troubleshoot virtual machines and supporting infrastructure.
- Administer device and application management through Microsoft Intune.
- Manage identity and access functions through Microsoft Entra ID, including authentication, authorization, and account troubleshooting.
- Diagnose and resolve advanced Microsoft platform and infrastructure issues beyond standard service desk support.
- Maintain secure and compliant administration practices within government cloud environments.
Compliance, Security & Regulated Environment Support- Apply practical knowledge of CMMC, NIST SP 800-171, and DoD IL4/IL5 requirements to daily IT operations.
- Support audit readiness activities by maintaining documentation, evidence, controls, and operational processes.
- Translate compliance requirements into sustainable service desk and systems administration practices.
- Partner with cybersecurity and IT stakeholders to ensure operational activities align with federal contractor requirements.
- Support identity management, device management, system configuration, documentation standards, and access controls with appropriate operational rigor.
- Assist in identifying and remediating gaps that may impact compliance requirements or assessment outcomes.
- Support internal and external assessments by providing technical expertise, documentation, and system evidence.
People Leadership & Capability Development- Lead, mentor, and develop service desk team members.
- Establish clear expectations and provide ongoing coaching and performance feedback.
- Strengthen team capabilities through knowledge sharing, technical guidance, and hands-on leadership.
- Balance leadership responsibilities with direct technical contribution and operational ownership.
- Foster collaboration across IT teams and business stakeholders to deliver a consistent and high-quality support experience.
Stakeholder Engagement & Continuous Improvement- Build trusted relationships through responsive, practical, and solution-oriented support.
- Communicate technical concepts, risks, priorities, and compliance requirements to both technical and non-technical audiences.
- Partner with cybersecurity and technology teams to improve service delivery and operational effectiveness.
- Identify opportunities for automation, process optimization, and long-term capability development.
- Contribute to the evolution and maturation of the organization's internal IT operating model.
What You Bring- 7+ years of IT experience, including hands-on systems administration responsibilities.
- At least 2 years of experience leading people, a service desk, or a technical support function.
- Deep experience administering Microsoft 365 GCC High environments.
- Strong hands-on expertise with:
- Microsoft 365 Admin Center
- Microsoft Entra ID
- Microsoft Intune
- Microsoft Defender
- Microsoft Teams
- Microsoft Exchange
- Microsoft SharePoint
- Azure Government
- Strong systems administration experience supporting users, devices, applications, virtual machines, and infrastructure.
- Experience leading Tier 1 through Tier 3 support operations, including escalation management, triage, prioritization, and service delivery oversight.
- Outstanding customer service, troubleshooting, communication, and problem-solving skills.
Preferred Qualifications- Experience supporting federal government agencies, Department of Defense contractors, or similarly regulated environments.
- Experience supporting environments subject to DoD IL4 and IL5 requirements.
- Practical experience working within NIST SP 800-171 regulated environments.
- Recent involvement supporting or participating in CMMC assessments or audits.
- Experience serving as an Information Systems Security Manager (ISSM).
- Relevant Microsoft certifications.
- Active or previously held U.S. government security clearance.
What Success Looks LikeIn this role, you will successfully balance leadership and technical execution by:
- Building a high-performing, accountable service desk team.
- Improving service quality, responsiveness, and ticket resolution performance.
- Strengthening internal technical capabilities and reducing dependency on external providers where appropriate.
- Maintaining secure, compliant, and well-documented operations across Microsoft government cloud platforms.
- Contributing to successful CMMC and NIST compliance efforts through disciplined operational execution.
- Delivering a reliable and productive technology experience for internal stakeholders.
Medical, dental, and vision insurance are available to qualified candidates who meet eligibility requirements.
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