IT/Helpdesk Supervisor

Ledgebrook

IT Helpdesk Supervisor responsible for leading IT support operations in a fully remote InsurTech company. Overseeing team performance and improving technical support processes globally.

Posted 4/24/2026full-timeRemote • 🇺🇸 United StatesMid-LevelSeniorWebsite

Tech Stack

Tools & technologies

DNSJamfMacOSServiceNow

About the role

Key responsibilities & impact

Lead day-to-day IT helpdesk operations and supervise support team performance
Manage and prioritize ticket queues to ensure timely resolution and SLA adherence
Serve as the escalation point for complex technical issues (Tier 2/3 support)
Coach, mentor, and develop helpdesk team members
Support hiring, onboarding, and training of new IT staff
Provide IT support for a fully remote workforce, including onboarding and offboarding
Troubleshoot issues across devices, networks, and SaaS applications
Administer and support core systems, including Google Workspace and other SaaS tools
Manage endpoint environments across Windows and macOS, including MDM platforms
Improve helpdesk workflows, automation, and overall operational efficiency
Maintain clear documentation and contribute to a scalable knowledge base
Deliver a high-quality support experience through clear communication and user-focused service

Requirements

What you’ll need

3–5+ years of IT support or helpdesk experience
1–3+ years of team leadership or supervisory experience
Experience supporting remote or hybrid work environments
Strong experience with Google Workspace administration
Proficiency supporting Windows and macOS environments
Experience with ticketing systems (e.g., Jira, ServiceNow, Freshservice)
Experience in a startup or high-growth environment (Preferred)
Familiarity with MDM tools (e.g., Jamf, Intune) (Preferred)
Understanding of networking fundamentals (DNS, DHCP, VPN) (Preferred)
Relevant certifications (CompTIA, Google Workspace, ITIL, etc.) (Preferred)

Benefits

Comp & perks

Competitive salary and meaningful equity ownership
Health Insurance 100% employer-paid option available (US only)
Additional benefits available include 401k plan, dental, vision & other options (US only)
Remote work, flexible hours
Unlimited time off policy
Ownership, autonomy, purpose

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

IT supporthelpdesk operationsticket managementtechnical troubleshootingGoogle Workspace administrationWindows supportmacOS supportMDM toolsnetworking fundamentalsautomation

Soft Skills

team leadershipcoachingmentoringcommunicationuser-focused serviceoperational efficiencydocumentationtrainingprioritizationproblem-solving

Certifications

CompTIAGoogle WorkspaceITIL