IT/Helpdesk Supervisor

Ledgebrook is an InsurTech MGA on a mission to bring Specialty insurance into the modern era. Burdened with legacy technology and processes, the industry has not kept pace with the speed of innovation seen in other sectors. Positioned at the cutting edge of the next generation of InsurTech, Ledgebrook offers the best of both worlds: innovative world-class technology deployed by a leadership team armed with over 100 years of insurance expertise.

Our long-term vision is to become a diversified full stack Specialty re/insurer competing with legacy carriers in product lines & markets across the globe. To get there, Ledgebrook will build our premium base by rolling out a new Specialty product every ~6 months until we prove enough traction to raise a balance sheet, become a full stack carrier and eventually compete in the reinsurance markets. Our initial product will be domestic primary and excess GL E&S policies sourced via wholesale brokers.

At Ledgebrook, everything we do is driven by our culture: Care, Strive, Thrive Together. To succeed in modernizing the industry, we must first succeed in changing the way we do business. Talent density is our north star—fewer, better people working together as one. To that end we’ve replaced all individual incentives with generous equity packages—we play as a team, we win as a team. Everyone benefits handsomely from Ledgebrook’s success. 

Ledgebrook is a fully-remote US based company backed by top venture investors including Brand Foundry & American Family Ventures.

• 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
• 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