Help Desk Analyst III

Windward Risk Managers is seeking an experienced Help Desk Analyst III to serve as a senior technical resource within the IT Help Desk. This hands-on position handles complex incidents and escalations that exceed Level 1 and Level 2 capabilities, independently drives issues through resolution, and partners with Infrastructure, Systems, Network, and Security teams on advanced troubleshooting. The successful candidate will also mentor junior technicians, strengthen documentation and operational standards, and contribute to endpoint management and technology rollouts while maintaining responsive end-user support.

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.

• Own and resolve advanced Level 2 escalations and complex Level 3 incidents; conduct root-cause analysis, document findings, and coordinate with specialist teams when infrastructure-level changes are required.
• Provide expert remote and onsite support for Windows 11 and macOS endpoints, including recurring operating system failures, application conflicts, device performance, encryption, driver and peripheral issues.
• Troubleshoot Microsoft 365 and Exchange Online issues involving Outlook, Teams, One Drive, shared mailboxes, permissions, licensing, authentication, and user productivity.
• Perform advanced Active Directory and Microsoft Entra , group, access and identity troubleshooting; follow approved access controls and change procedures.
• Diagnose client-side network and remote access issues using DNS, DHCP, TCP/IP, Wi-Fi and VPN troubleshooting; collaborate with Network and Security teams on upstream causes.
• Use Ninja One and other approved remote management tools to investigate endpoint health, deploy software, execute vetted scripts, support patch remediation, and improve endpoint consistency.
• Lead technically complex onboarding, offboarding, device replacement, reimaging and hardware lifecycle tasks, ensuring accurate provisioning and asset records.
• Provide technical ownership for Help Desk work streams in system migrations, operating system upgrades, software deployments, service catalog improvements, and ticketing platform initiatives.
• Mentor Level 1 and Level 2 analysts through ticket reviews, troubleshooting guidance and knowledge transfer; help establish clear escalation standards and reduce repeat incidents.
• Maintain accurate tickets, troubleshooting notes, knowledge articles and SOPs; adhere to security, audit, change management and documentation requirements.
• Identify recurring incidents, propose automation and preventive fixes, and contribute to service quality, response-time and resolution improvements.
• Communicate clearly with end users, management and cross-functional technical teams during high-priority incidents and outages.

• 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

• At least 5 years of progressive hands-on IT support experience, including substantial Level 2 troubleshooting and demonstrated ownership of senior-level escalations; equivalent relevant experience will be considered.
• Strong practical knowledge of Windows endpoint support, Microsoft 365, Exchange Online, Active Directory and Microsoft Entra .
• Demonstrated ability…