IT/Helpdesk Supervisor (Rippling Experience)

About Our Client

The organization operates in the InsurTech sector, focusing on modernizing Specialty insurance, which has traditionally faced challenges due to outdated technology and processes. Positioned at the forefront of InsurTech innovation, the company combines advanced technology with extensive insurance expertise to develop new Specialty insurance products. It aims to expand globally by continually introducing new products and evolving into a full stack Specialty re/insurer competing with established carriers.

About the Opportunity

The IT/Helpdesk Supervisor leads and scales the daily IT support operations, ensuring reliable and secure technical assistance for a fully remote workforce across multiple continents. This role is critical for maintaining efficient IT support workflows, supervising the helpdesk team, and enhancing user experience through continuous process improvements.

Responsibilities

• Lead daily IT helpdesk operations and supervise team performance
• Manage and prioritize ticket queues to meet resolution timelines and service levels
• Act as escalation point for complex technical issues (Tier 2/3 support)
• Coach and develop helpdesk team members
• Support hiring, onboarding, and training of IT staff
• Provide IT support for a fully remote workforce, including onboarding and offboarding
• Troubleshoot issues across devices, networks, and SaaS applications
• Administer core systems such as Google Workspace and other SaaS tools
• Manage endpoint environments on Windows and macOS, including MDM platforms
• Improve helpdesk workflows, automation, and operational efficiency
• Maintain clear documentation and contribute to a knowledge base
• Deliver user-focused support with clear communication

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 Google Workspace administration skills
• Proficiency with Windows and macOS environments
• Experience with ticketing systems such as Jira, ServiceNow, or Freshservice
• Experience with Rippling
• PREFERRED: Experience in startup or high-growth environments
• Familiarity with MDM tools (e.g., Jamf, Intune)
• Understanding of networking fundamentals (DNS, DHCP, VPN)
• Relevant certifications (CompTIA, Google Workspace, ITIL)

Pay Range and Compensation Package

Base salary range $75,000-$100,000, subject to factors such as experience and location
Eligibility to participate in the organization’s equity incentive program

Benefits & Perks

• Competitive salary and equity ownership
• Health insurance with 100% employer-paid option (US only)
• Additional benefits including 401(k), dental, vision, and other options (US only)
• Remote work and flexible hours
• Unlimited time off policy
• Ownership, autonomy, and purposeful work environment

Equal Opportunity Statement

Our client is an equal opportunity employer. They celebrate diversity and are committed to creating an inclusive environment for all employees. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, or national origin.