IT/Helpdesk Supervisor – Rippling Experience

Job not on LinkedIn

🕒 July 8

🇺🇸 United States – Remote

💵 $75k - $100k / year

⏰ Full Time

🟡 Mid-level

🟠 Senior

💻 IT Support

👻 Ghost score 19%

What it means: the chance that no one is really hiring for this job.How to read it: 60% or higher means we think this is a ghost. Lower scores are less of a worry.How we score it: age, reposts, open roles vs team size, how fast jobs close, and whether pay is listed.Fine print: an estimate from public data, not a judgment of the company. Real jobs can score high, so treat it as a hint, not a fact.

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Ledgebrook

WebsiteLinkedInAll Job Openings

51 - 200 employees

Founded 2021

🛡️ Insurance

🤝 B2B

💸 Finance

🔥 Funding within the last year

💰 $65M Series C on 2025-07

Insurance • B2B • Finance

<Ledgebrook> is a tech-enabled Excess & Surplus (E&S) managing general agent (MGA) that provides fast, data-driven quoting and underwriting services to wholesale brokers. Ledgebrook combines a next-generation tech stack, modeling and analytics, and experienced underwriters to deliver rapid, streamlined submissions and casualty products such as general liability and professional liability.

📋 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

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