Help Desk Analyst II
Summary
Windward Risk Managers is hiring a Help Desk Analyst II at its Boca Raton, FL office to work the IT support queue, take escalated tickets beyond Level 1 scope, and support end users across Windows and macOS. Day-to-day involves Active Directory/Microsoft 365 account tasks, hardware and printer troubleshooting, onboarding/offboarding, and patching/remote sessions via the NinjaOne RMM.
Position Summary:
Windward Risk Managers is seeking a proficient Help Desk Analyst II to join our IT Help Desk team. The successful candidate will work the IT support queue alongside Level 1 staff, taking on more complex tickets and serving as a point of escalation for issues that go beyond the Level 1 scope. This role is crucial in maintaining the day-to-day reliability and efficiency of our IT operations, and works closely with senior Infrastructure, Systems, and Security staff to keep end users productive and supported.
Work Location
This is a full-time, in-person position based at our Boca Raton, Florida office during regular business hours. Remote and hybrid work arrangements are not available for this role.
Key Responsibilities:
- Work the IT support queue alongside Level 1 staff, responding to user requests via email, phone, and our ticketing system, while also taking on more complex tickets and escalations that require additional experience and troubleshooting depth.
- Provide remote and hands-on support across our Windows and macOS environments, including hardware troubleshooting, software installation, peripheral and printer issues, and basic network connectivity problems.
- Perform user account and access tasks in Active Directory and Microsoft 365, including password resets, account creation, group membership changes, mailbox configuration, and license assignments.
- Support employee onboarding and offboarding, including account provisioning, device preparation, software installation, and account decommissioning.
- Assist with end-user training, providing walkthroughs and guidance on company applications, tools, and IT processes for new hires and during the rollout of new systems.
- Use our RMM platform (NinjaOne) to deploy software, push patches, run remote sessions, and assist with routine endpoint maintenance.
- Monitor system reports and alerts, flagging deviations and escalating to higher-tier staff when appropriate.
- Assist with small IT projects and rollouts, such as hardware refreshes and software deployments, under the direction of senior staff.
- Provide guidance and knowledge sharing to Level 1 analysts, helping them grow into more complex troubleshooting work.
- Maintain accurate documentation of common issues, resolutions, and changes, contributing to the IT knowledge base and asset management records.
Why Windward Risk Managers:
- Windward Risk Managers is proud to be recognized on Fortune's 2026 Best Medium Workplaces list, ranking #28 among the Top 100 companies
- 100% employer paid health insurance for employees
- Up to 6% 401(k) match with immediate vesting
- Long-term and short-term disability insurance
- 3 weeks PTO to start + generous paid holidays
- Tuition reimbursement and continuing education support
- Collaborative and growth focused culture