Help Desk Analyst III

Windward Risk Managers is seeking a Help Desk Analyst III to provide senior-level support for complex Level 2 and Level 3 escalations, while partnering with Infrastructure, Systems, Network, and Security teams to drive advanced troubleshooting. This is a full-time, in-person role in Boca Raton, FL during regular business hours, focused on hands-on problem solving, strong customer support, and continuous improvement to Help Desk operations.

What you’ll get

• 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 plus generous paid holidays
• Tuition reimbursement and continuing education support

Key responsibilities

• Independently own and resolve advanced Level 2 escalations and complex Level 3 incidents, performing root-cause analysis, documenting findings, and coordinating with specialist teams when infrastructure-level changes are required.
• Deliver expert remote and onsite support for Windows 11 and macOS endpoints, including recurring OS failures, application conflicts, device performance, encryption, and driver and peripheral issues.
• Troubleshoot Microsoft 365 and Exchange Online problems involving Outlook, Teams, OneDrive, shared mailboxes, permissions, licensing, authentication, and end-user productivity.
• Handle advanced Active Directory and Microsoft Entra ID account, group, access, and identity troubleshooting while following approved access controls and change procedures.
• Diagnose client-side network and remote access issues using DNS, DHCP, TCP/IP, Wi-Fi, and VPN troubleshooting, coordinating 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, and support patch remediation to 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, helping establish clear escalation standards to reduce repeat incidents.
• Maintain accurate tickets, troubleshooting notes, knowledge articles, and SOPs, and comply with security, audit, change management, and documentation requirements.
• Identify recurring incidents and propose automation or preventive fixes to improve service quality, response time, and resolution outcomes.
• Communicate clearly with end users, management, and cross-functional technical teams during high-priority incidents and outages.

What you bring

• 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 considered).
• Strong working knowledge of Windows endpoint support, Microsoft 365, Exchange Online, Active Directory, and Microsoft Entra ID.
• Proven ability to independently diagnose complex issues across hardware, software, identity, connectivity, and endpoint management, not relying only on scripted troubleshooting.
• Working knowledge of DNS, DHCP, TCP/IP, VPN, and common network troubleshooting tools.
• Experience with RMM platforms, remote support, patching, software deployment, and endpoint lifecycle management.
• Experience using an ITSM ticketing platform and maintaining thorough, audit-ready ticket documentation.
• Strong judgment, prioritization, customer service, communication, and mentoring skills, with the ability to work effectively in a fast-paced onsite environment.
• Authorization to work in the U.S. for any employer without requiring visa sponsorship now or in the future.

Technologies you’ll work with

Windows 11, macOS, Microsoft 365, Exchange Online, Outlook, Teams, OneDrive, Active Directory, Microsoft Entra ID, DNS, DHCP, TCP/IP, Wi-Fi, VPN, NinjaOne, RMM, ITSM ticketing platform, PowerShell, Microsoft Intune, Microsoft MD-102, CompTIA Network+, CompTIA Security+, HaloITSM, ManageEngine ServiceDesk Plus.

Role expectations

• This is a senior individual-contributor position, not a people-management role.
• The Analyst III stays actively engaged in the support queue, maintains primary ownership of escalated technical issues, mentors junior analysts, and helps improve Help Desk operations.

Location and work model

• Full-time, in-person at the Boca Raton, Florida office
• Remote and hybrid work arrangements are not available for this role

States currently hired

AL, AR, CA, CT, FL, GA, KY, MO, NC, NV, OH, SC, TN, TX, VA, WI

Notice to third-party agencies

WRM does not accept unsolicited resumes from third-party recruiting firms. Absent a signed Service Agreement by WRM’s Human Resources Department, WRM reserves the right to pursue and hire candidates without financial obligation to recruiters or agencies.