Helpdesk Lead (MSP)

Onsite: Rockville, MD

Position Summary

The Senior Service Desk Technician serves as a hands-on technical leader within the Service Desk and is responsible for resolving advanced support requests, coaching and developing Service Desk technicians, and serving as the primary escalation resource within the Help Desk. This role bridges the gap between frontline support and the Engineering Team by handling more complex technical issues, improving troubleshooting effectiveness, reinforcing service standards, and ensuring that only appropriate issues require engineering involvement.

This position remains a hands-on support role with a primary focus on ticket resolution, client support, and service delivery. The ideal candidate is resourceful, takes ownership of issues from start to finish, continuously develops their technical skills, and is committed to delivering exceptional service to clients and teammates.

Success in this role is measured not only by individual performance, but by the overall effectiveness, technical capability, and maturity of the Service Desk.

Primary Responsibilities

Service Desk Support

• Respond to and resolve client service requests in accordance with service standards and SLAs.
• Provide remote and onsite technical support for end users, workstations, mobile devices, printers, and business applications.
• Perform user onboarding, offboarding, workstation deployment, and account administration tasks.
• Maintain accurate ticket documentation, time entries, and resolution notes.
• Deliver professional and timely client communication throughout the support process.
• Maintain ownership of assigned incidents through resolution.

Advanced Troubleshooting & Escalation Management

• Serve as the primary escalation resource for Tier 1 Service Desk technicians.
• Troubleshoot and resolve advanced Microsoft 365, Windows, networking, security, and cloud-related issues.
• Research and investigate unfamiliar problems utilizing vendor resources, documentation, knowledge bases, and independent troubleshooting methodologies.
• Gather and document sufficient technical information before involving Engineering resources.
• Ensure escalations to Engineering are well documented, properly qualified, and include all relevant troubleshooting performed.
• Partner with Engineering when necessary while maintaining ownership and communication responsibility for the client experience.
• Increase the percentage of issues resolved within the Service Desk.

Microsoft 365 & Systems Administration

• Administer Microsoft 365 environments, including user management, licensing, device management, security, collaboration, and productivity services.
• Support Windows Server and Active Directory environments.
• Assist with backup management, endpoint security administration, and infrastructure support activities.
• Perform network troubleshooting involving DNS, DHCP, VPN connectivity, firewalls, wireless networking, and related technologies.
• Support cybersecurity best practices and security-related remediation activities.

Team Development & Service Excellence

• Mentor, coach, and develop Service Desk technicians by sharing troubleshooting methodologies, technical knowledge, and best practices.
• Serve as a technical resource and escalation point for Service Desk team members.
• Reinforce Service Desk standards for ticket documentation, troubleshooting quality, client communication, and escalation readiness.
• Review recurring escalations and identify opportunities for coaching, knowledge transfer, documentation improvements, and process enhancements.
• Contribute to and maintain knowledge base articles, SOPs, and technical documentation.
• Identify recurring issues and recommend improvements that increase efficiency and reduce escalations.
• Help improve Service Desk effectiveness through standardization, documentation, and continuous improvement initiatives.

Required Qualifications

• 5+ years of hands-on IT support experience.
• MSP experience strongly preferred. Candidates without MSP experience should have significant experience handling Tier 2/Tier 3 Service Desk escalations within a larger, complex IT environment.
• Demonstrated ability to troubleshoot advanced technical issues independently.
• Experience supporting Microsoft 365 environments.
• Prior experience mentoring junior technicians or serving as a senior technical resource within a support organization.
• Strong customer service and communication skills.
• Ability to manage multiple priorities across multiple client environments.
• Strong organizational skills and attention to detail.
• Demonstrated ability to learn new technologies and troubleshoot unfamiliar issues through research, critical thinking, and persistence.

Technical Competencies

Core Technical Proficiency

• Microsoft 365 platform administration and support, including Exchange Online, SharePoint Online, Teams, Entra ID, Intune, Defender, and related services.
• Windows 10/11 administration and troubleshooting.
• Windows Server administration and support.
• Active Directory and Group Policy.
• DNS, DHCP, VPN, and networking fundamentals.
• Firewall administration and network troubleshooting.
• Backup and disaster recovery solutions.
• Endpoint management and security best practices.
• Troubleshooting authentication, connectivity, performance, and user support issues across cloud and on-premises environments.

MSP Tooling & Service Delivery

• PSA platforms (ConnectWise preferred).
• RMM platforms.
• Remote support tools.
• Documentation and knowledge management platforms ( IT Glue preferred
• Ticket queue management.
• Knowledge base administration.
• Service Desk workflows and escalation procedures.

Technology Stack & Strategic Partnerships

Support a wide variety of small and mid-sized business technology environments. Team members in this role will regularly work with technologies and vendor solutions including:

• Microsoft 365
• Microsoft Intune
• Microsoft Defender
• ConnectWise PSA
• ConnectWise RMM
• IT Glue
• Blackpoint Cyber
• SonicWall
• Aruba
• Veeam
• Datto
• Egnyte
• Windows Server
• Active Directory

This section is intended to provide visibility into technology stack and strategic partner ecosystem and should not be viewed as a comprehensive list of supported technologies.

Professional Skills

• Advanced troubleshooting and problem solving.
• Resourcefulness and investigative mindset.
• Technical coaching and knowledge transfer.
• Customer service and relationship management.
• Documentation and communication.
• Time management and prioritization.
• Ability to work independently while collaborating effectively with teammates.

Preferred, Not Required

• Microsoft 365 certifications.
• Azure certifications.
• CompTIA Network+.
• CompTIA Security+.
• Other relevant Microsoft or industry certifications.

Practical MSP experience, troubleshooting ability, accountability, and technical leadership experience are valued more heavily than certifications alone.

The ideal candidate for this role:

• Takes ownership of issues from assignment through resolution, follows through on commitments, and demonstrates Be Accountable by doing what they say they're going to do and communicating proactively when obstacles arise.
• Approaches unfamiliar problems with curiosity, persistence, and a commitment to continuous learning, reflecting Do Better, Be Better Every Day . They are resourceful, willing to research, and always looking for opportunities to improve their technical skillset.
• Investigates issues thoroughly, validates assumptions, gathers facts, and develops informed solutions before escalating, embodying Seek the Truth . They understand that good troubleshooting starts with understanding the full picture.
• Works collaboratively with Service Desk and Engineering teammates to achieve outcomes greater than any individual could accomplish alone, demonstrating More Than the Sum of Individual Parts
• Builds trust with clients and coworkers through professionalism, empathy, and exceptional service, reflecting Relationships Are #1
• Maintains a positive attitude, keeps perspective during stressful situations, and contributes to an environment where teammates and clients enjoy working with GURU, embracing Make It F*cking Enjoyable
• Approaches challenges honestly, professionally, and with a focus on solutions rather than blame, consistent with No Drama or Bullsh*t
• Demonstrates a commitment to quality in everything they do, from troubleshooting and documentation to client communication and follow-through, reflecting Pride in Our Work, Seen or Unseen
• Acts with integrity, professionalism, and a genuine desire to help others, embodying Do the Right Thing even when it requires additional effort or difficult conversations.

Success Measures

Success in this role is demonstrated through:

• Increased Service Desk resolution rates.
• Reduced avoidable escalations to Engineering.
• Improved quality, completeness, and consistency of escalated tickets.
• Reduced ticket aging and stalled tickets.
• Improved technical capabilities across the Service Desk team.
• Increased utilization and quality of knowledge base documentation.
• Positive client satisfaction scores and feedback