<h3>Description</h3><p><a href="https://himalayas.app/companies/ledgebrook">Ledgebrook</a> 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, <a href="https://himalayas.app/companies/ledgebrook">Ledgebrook</a> offers the best of both worlds: innovative world-class technology deployed by a leadership team armed with over 100 years of insurance expertise.</p><p>Our long-term vision is to become a diversified full stack Specialty re/insurer competing with legacy carriers in product lines &amp; markets across the globe. To get there, <a href="https://himalayas.app/companies/ledgebrook">Ledgebrook</a> 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&amp;S policies sourced via wholesale brokers.</p><p>At <a href="https://himalayas.app/companies/ledgebrook">Ledgebrook</a>, 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 <a href="https://himalayas.app/companies/ledgebrook">Ledgebrook</a>’s success. </p><p><a href="https://himalayas.app/companies/ledgebrook">Ledgebrook</a> is a fully-remote US based company backed by top venture investors including Brand Foundry &amp; American Family Ventures.</p><h3>About the Role</h3><p>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.</p><p>This role requires a balance of leadership, technical depth, and strong customer service skills in a dynamic, growth-oriented organization.</p><h3>Key Responsibilities</h3><ul><li>Lead day-to-day IT helpdesk operations and supervise support team performance</li><li>Manage and prioritize ticket queues to ensure timely resolution and SLA adherence</li><li>Serve as the escalation point for complex technical issues (Tier 2/3 support)</li><li>Coach, mentor, and develop helpdesk team members</li><li>Support hiring, onboarding, and training of new IT staff</li><li>