IT/Helpdesk Supervisor – Rippling Experience

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🕒 July 8

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Ledgebrook

WebsiteLinkedInAll Job Openings

51 - 200 employees

Founded 2021

💸 Finance

💳 Fintech

🛡️ Insurance

💰 Series B on 2024-09

Finance • Fintech • Insurance

Ledgebrook is a tech-enabled E&S managing general agent (MGA) that provides wholesale brokers with a fast and efficient quoting experience. With a focus on speed and technology-driven underwriting solutions, Ledgebrook utilizes advanced modeling and analytics to deliver quotes rapidly and enhance broker submissions. The company offers various insurance products, including general liability, professional liability, and excess casualty coverage, ensuring tailored solutions for specific client needs.

📋 Description

• 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

🎯 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) • Experience with Rippling • Relevant certifications (CompTIA, Google Workspace, ITIL, etc.)

🏖️ 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