IT/Helpdesk Supervisor (Rippling Experience)

Description

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.

About the Role

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.

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 you

Here 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

Requirements

Required:

• 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

Compensation

• Base Salary Range $75,000-$100,000. This is a good-faith compensation range based on what Ledgebrook reasonably expects to pay for this position at the time of this posting. Actual compensation may vary based on a variety of relevant factors including experience, qualifications, geographic location and other relevant factors.
• Employees in this position are eligible to participate in Ledgebrook’s equity incentive program.