Lead and scale IT support operations for a fully remote workforce. Oversee helpdesk performance, manage ticket workflows, and handle escalations while improving systems and user experience. Requires 3-5+ years IT support experience with 1-3+ years leadership experience and strong Google Workspace, Windows, and macOS expertise.
Key Highlights
Key Responsibilities
Technical Skills Required
Benefits & Perks
Nice to Have
Job Description
IT Helpdesk Supervisor (Remote, US-Based)
About Us
We are a high-growth, venture-backed InsurTech company modernizing the specialty insurance industry through advanced technology and deep expertise. Our goal is to build a global, full-stack re/insurer—powered by a high-performing, collaborative team that shares in our success through meaningful equity ownership.
Role Overview
We’re looking for an IT Helpdesk Supervisor to lead and scale IT support operations for a fully remote workforce. Reporting to the Head of IT, you’ll oversee helpdesk performance, manage ticket workflows, and handle escalations while improving systems and user experience.
Key Responsibilities
- Lead helpdesk operations and supervise team performance
- Manage ticket queues and ensure SLA adherence
- Act as Tier 2/3 escalation point
- Support hiring, onboarding, and development of IT staff
- Provide remote support across devices, networks, and SaaS tools
- Administer Google Workspace and endpoint environments (Windows/macOS, MDM)
- Improve workflows, automation, and documentation
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Requirements
- 3–5+ years IT support experience
- 1–3+ years leadership experience
- Experience supporting remote environments
- Strong Google Workspace, Windows, and macOS expertise
- Experience with ticketing systems (e.g., Jira, ServiceNow)
Preferred
- Startup or high-growth experience
- Familiarity with MDM tools (Jamf, Intune)
- Networking fundamentals (DNS, DHCP, VPN)
- Relevant certifications (CompTIA, ITIL, etc.)
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What We Value
Innovative, proactive, growth-oriented team players who take ownership and strive for excellence.
Benefits
- Competitive salary + equity
- 100% employer-paid health insurance option (US)
- 401(k), dental, vision (US)
- Fully remote, flexible hours
- Unlimited time off
If you are interested please email a copy of your CV to [email protected] for immediate consideration.
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