IT Service Desk Lead

Location: Chicago, IL Salary: $65.00 USD Hourly - $80.00 USD Hourly Description:
IT Service Desk Lead
Location and Work Arrangement
Arlington, Virginia
Onsite, five days per week
Role Overview
We 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 Do
Service 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 Like
In 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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