DescriptionAbout the RoleThe 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.
Key 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
About youHere at Ledgebrook we are passionate about creating a team that is on a continuous learning journey and that shares our excitement about building a company from the ground up. We don't just want someone to follow a checklist; we want a builder who is:
- Innovative: You aren't satisfied with the status quo and constantly seek to optimize test execution time and reliability.
- Growth-Oriented: You have a hunger for mentorship and staying current with the evolving JavaScript/TypeScript ecosystem.
- Agile & Urgent: You balance the "keener sense of urgency" with the architectural discipline to "do it right" the first time.
- Principled: You hold yourself and your code to high standards, maintaining a "do the right thing" mentality in a high-performing, non-toxic environment.
- Proactive: A strong drive and desire to win together as a high-performing team
RequirementsRequired:- 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 with Rippling
Preferred:- 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.)
Please note: This position is open only to candidates who are authorized to work in the United States without the need for current or future employer-sponsored work authorization. We are unable to offer visa sponsorship at this time
Benefits- 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
