IT/Helpdesk Supervisor Job Description

Ledgebrook

17h • Remote

About The Position

The IT Helpdesk Supervisor is responsible for leading and scaling day-to-day IT support operations in a fast-paced startup environment. Working closely with the Head of IT, this role ensures reliable, secure, and efficient technical support for a remote workforce spanning the US, Europe, and Asia. You will supervise the helpdesk team, manage ticketing workflows, and act as a hands-on escalation point while continuously improving IT processes, tooling, and end-user experience. This role requires a balance of leadership, technical depth, and strong customer service skills in a dynamic, growth-oriented organization.

Requirements

• 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)
• Authorized to work in the United States without the need for current or future employer-sponsored work authorization

Nice To Haves

• Experience in a startup or high-growth environment
• Familiarity with MDM tools (e.g., Jamf, Intune)
• Understanding of networking fundamentals (DNS, DHCP, VPN)
• Relevant certifications (CompTIA, Google Workspace, ITIL, etc.)

Responsibilities

• 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

Benefits

• Competitive salary and meaningful equity ownership
• Health Insurance 100% employer-paid option available (US only)
• 401k plan
• Dental
• Vision
• Other options (US only)
• Remote work
• Flexible hours
• Unlimited time off policy
• Ownership, autonomy, purpose

What This Job Offers

• Job Type: Full-time
• Career Level: Entry Level
• Education Level: No Education Listed