The Support Lead/Deputy Program Lead provides day-to-day leadership, operational oversight, and technical guidance for a team of Support Desk Technicians responsible for Microsoft-based end-user services. This position combines hands-on technical support with team leadership, ensuring responsive, consistent, and high-quality service delivery across the support environment.
The Support Lead manages daily workload distribution, ticket queues, staffing coverage, service-level performance, and escalation activities while serving as a senior technical resource for the team. The position works closely with systems administrators, network engineers, cybersecurity personnel, and IT leadership to resolve complex issues and improve overall support operations.
The ideal candidate is an experienced IT support professional who can lead a technical team, troubleshoot complex Microsoft environments, mentor junior staff, and identify opportunities to modernize and improve service desk operations.
Location: Chesapeake, VA / Suffolk, VA
Job Type: Full-Time
Education: Bachelor's Degree or Equivalent Experience
Certification: CompTIA Security+ Required
Essential Duties and Responsibilities
Team Leadership & Operations
- Provide daily leadership, direction, and technical guidance to Support Desk Technicians.
- Oversee day-to-day service desk operations and ensure timely response and resolution of incidents and service requests.
- Assign, prioritize, and balance workloads based on business priorities, technician capabilities, and ticket volume.
- Monitor ticket queues for SLA compliance, aging tickets, priority issues, and documentation quality.
- Serve as the first level of escalation for Tier I technicians, providing troubleshooting assistance and technical decision-making.
- Conduct daily or weekly team meetings to communicate priorities, operational changes, technical issues, and organizational updates.
- Manage staffing schedules and coordinate coverage for planned leave, after-hours support, and periods of increased demand.
- Promote a professional, customer-focused, and collaborative support environment.
Technical Support & Escalation
- Provide advanced hands-on troubleshooting for Microsoft 365, Windows 10/11, Entra ID, Azure Virtual Desktop, and standard productivity applications.
- Troubleshoot user account, authentication, MFA, permissions, connectivity, device, application, and access issues.
- Support Microsoft 365 services, including Outlook/Exchange Online, Teams, SharePoint Online, and OneDrive.
- Troubleshoot SharePoint and OneDrive synchronization, permissions, access, and file recovery issues.
- Assist with complex incidents requiring elevated permissions, deeper technical analysis, or cross-functional coordination.
- Coordinate escalations with systems administrators, network engineers, cybersecurity teams, and other IT personnel.
- Support user onboarding and offboarding processes and ensure consistent execution of established procedures.
- Provide technical assistance during outages, high-impact incidents, system changes, and other operational events.
Quality Assurance & Service Improvement
- Monitor support desk performance through ticket audits, user feedback, SLA metrics, and operational KPIs.
- Conduct ticket-quality reviews to ensure accurate documentation, appropriate troubleshooting, and timely resolution.
- Identify recurring incidents and coordinate root-cause analysis with Tier II/III support teams.
- Develop, update, and enforce Standard Operating Procedures (SOPs) and support procedures.
- Maintain and expand the service desk knowledge base and promote effective documentation practices.
- Identify opportunities to automate, streamline, and modernize support desk workflows.
- Recommend improvements to tools, processes, staffing models, and service delivery practices.
- Lead or support initiatives designed to improve efficiency, customer satisfaction, and first-contact resolution.
Training & Staff Development
- Mentor and coach Support Desk Technicians to improve technical capabilities and customer-service skills.
- Provide constructive performance feedback and identify training and development opportunities.
- Facilitate onboarding and technical training for new support personnel.
- Develop or coordinate training materials, job aids, and knowledge-base resources.
- Encourage professional development and certification pathways aligned with organizational requirements.
- Identify technical skill gaps and recommend targeted training or development plans.
Reporting & Communication
- Generate and analyze reports covering ticket volume, SLA performance, resolution times, recurring incidents, and service trends.
- Provide management with visibility into support desk performance, staffing requirements, operational risks, and emerging issues.
- Communicate service disruptions, planned maintenance, and high-impact incidents to affected users and stakeholders.
- Serve as a liaison between support personnel, IT leadership, end users, and technical teams.
- Escalate significant service issues and operational risks appropriately and in a timely manner.
- Maintain clear and professional communication across technical and non-technical audiences.
Required Qualifications
- Bachelor's degree in Information Technology, Computer Science, Information Systems, Cybersecurity, or a related field, or equivalent combination of education and experience.
- 7+ years of experience in an IT support, service desk, or technical support environment.
- At least 1 year of experience in a lead, senior, supervisory, or technical mentoring role.
- Strong working knowledge of:
- Microsoft 365, including Outlook/Exchange Online, Teams, SharePoint, and OneDrive
- Windows 10/11 troubleshooting and administration
- Microsoft Entra ID (Azure AD)
- Azure Virtual Desktop
- User accounts, permissions, MFA, and basic Conditional Access concepts
- Basic networking concepts, including DNS, DHCP, VPN, and TCP/IP
- Experience with enterprise IT Service Management (ITSM) platforms such as ServiceNow, Jira Service Management, Zendesk, or similar systems.
- Demonstrated ability to lead, mentor, and provide technical direction to support personnel.
- Strong troubleshooting, analytical, organizational, and problem-solving skills.
- Excellent written and verbal communication and customer-service skills.
- Strong technical documentation skills and attention to detail.
- Demonstrated experience performing ticket quality assurance and improving service desk workflows.
- CompTIA Security+ certification required or ability to obtain prior to employment.
Required Certifications
- CompTIA Security+
- Microsoft Azure Fundamentals (AZ-900) - required within 90 days of employment.
- Microsoft 365 Certified: Copilot and Agent Administration Fundamentals (AB-900) - required within 90 days of employment.
Preferred Qualifications
- Experience with Microsoft Intune, Endpoint Manager, or Configuration Manager (SCCM/ConfigMgr).
- Experience administering Microsoft 365 through the Exchange Online, Teams, SharePoint, and Entra ID admin centers.
- Working knowledge of PowerShell for automation, reporting, troubleshooting, and bulk administrative tasks.
- Experience developing and maintaining SOPs, knowledge bases, technical documentation, and training materials.
- Experience leading ticket-quality programs, workflow improvements, or service desk performance initiatives.
- Experience transforming, modernizing, or improving traditional help desk or call center operations.
- Experience implementing service desk automation, self-service capabilities, or knowledge-centered support practices.
- Experience supporting enterprise or government IT environments.
- Familiarity with ITIL-based service management practices.
Core Competencies
- Technical Leadership
- Customer Service
- Advanced Troubleshooting
- Team Development & Mentoring
- Incident & Problem Management
- ITSM & SLA Management
- Process Improvement
- Documentation & Knowledge Management
- Microsoft 365 Administration
- Communication & Collaboration
Work Location
This is an on-site position supporting operations in Chesapeake, Virginia and Suffolk, Virginia. The selected candidate must be able to report to the assigned work location as required.
The anticipated salary range for this role is $140,000 to $175,000 annually. The anticipated salary range for this position is provided in accordance with applicable pay transparency laws. The final starting salary will be determined based on a variety of job-related factors, including the selected candidate's qualifications, skills, relevant experience, education, certifications, and work location (where applicable), as well as internal equity and market considerations.
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