IT Helpdesk Supervisor

Reporting directly to the Chief Information Officer, this working-lead role manages daily service desk workflows, delivers Tier 2 and Tier 3 technical escalation support, and administers cloud, endpoint, and core business applications., Supervise daily helpdesk queue activity, prioritize incoming tickets, enforce service level standards, and serve as the primary escalation point for unresolved issues.

Administer Microsoft 365 services, including Exchange Online, Teams, SharePoint, and OneDrive.

Manage identity lifecycle, user provisioning, access changes, Single Sign-On, and MFA within Microsoft Azure and Entra ID.

Provide operational support, user configuration, and vendor troubleshooting for core insurance platforms, including AMS360, ImageRight, and BenefitPoint.

Build, image, configure, deploy, and maintain corporate laptops, desktop workstations, monitors, and peripherals.

Create standardized troubleshooting guides, technician runbooks, user self-service documentation, and new-hire onboarding guides.

Coordinate technology support for conference rooms, virtual meetings, telecommunications, and office hardware setups.

Collaborate closely with the CIO on infrastructure projects, security compliance, technology roadmaps, and IT department initiatives.

4+ years of hands-on experience in IT service desk, desktop support, or technical helpdesk environments, including 1-2 years in a team lead, supervisory, or senior escalation capacity.

• Demonstrated administrative proficiency across the Microsoft 365 platform and Microsoft Azure / Entra ID.

• Solid understanding of endpoint management tools, Windows environments, and foundational networking concepts like DNS, DHCP, and VPNs.

• Proven track record delivering responsive, professional, and patient technical support to employees at all organizational levels.

• Career ambition to grow into senior IT management under direct executive mentorship.

• Bachelor’s degree in Information Technology, Computer Science, or equivalent practical experience.

• Prior technical support experience within an insurance brokerage or financial services firm.

• Practical familiarity supporting Vertafore AMS360, ImageRight, or BenefitPoint.

• Relevant industry certifications such as Microsoft 365 Certified, Azure Fundamentals, or CompTIA (A+, Network+, Security+).

Pay offered to a successful candidate will be based on several factors including the candidate’s education, work experience, work location, specific job duties, certifications, etc. In addition, Randstad Digital offers a comprehensive benefits package, including: medical, prescription, dental, vision, AD&D, and life insurance offerings, short-term disability, and a 401K plan (all benefits are based on eligibility).

This posting is open for thirty (30) days.

Qualified applicants in San Francisco with criminal histories will be considered for employment in accordance with the San Francisco Fair Chance Ordinance.

Qualified applicants with arrest or conviction records will be considered for employment in accordance with the Los Angeles County Fair Chance Ordinance for Employers and the California Fair Chance Act.

We will consider for employment all qualified Applicants, including those with criminal histories, in a manner consistent with the requirements of applicable state and local laws, including the City of Los Angeles’ Fair Chance Initiative for Hiring Ordinance.