Help Desk Analyst III
Windward Risk Managers · Corporate Office - Boca Raton, FL 33487 · hybrid
POSITION SUMMARY:
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.
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:
• 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, OneDrive, shared
mailboxes, permissions, licensing, authentication, and user productivity.
• Perform advanced Active Directory and Microsoft Entra ID account, 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 NinjaOne 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 workstreams 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.
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