Job description

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 REQUIRED QUALIFICATIONS: • 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 ID. • Demonstrated ability to independently diagnose complex hardware, software, identity, connectivity and endpoint management issues rather than relying solely on scripted troubleshooting. • Working knowledge of DNS, DHCP, TCP/IP, VPN connectivity 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; ability to work effectively in a fast-paced onsite support environment. PREFERRED QUALIFICATIONS: • CompTIA Network+, Security+, Microsoft MD-102, or comparable relevant certification. • Hands-on experience with NinjaOne, HaloITSM or ManageEngine ServiceDesk Plus. • Experience with PowerShell for troubleshooting and approved endpoint automation. • Experience supporting a multi-site, security-conscious or regulated organization, including documented access controls and change management. • Exposure to endpoint security tools, Microsoft Intune, and cross-functional incident response. ROLE EXPECTATIONS: This is a senior individual-contributor position, not a people-management role. The Analyst III remains actively engaged in the support queue while taking primary ownership of escalated technical issues, mentoring junior analysts, and helping improve Help Desk operations. Due to current business and operational considerations, we currently hire employees residing in the following states at this time: AL, AR, CA, CT, FL, GA, KY, MO, NC, NV, OH, SC, TN, TX, VA , and WI . Candidates must be authorized to work for any employer in the U.S. without requiring visa sponsorship now or in the future. WRM is committed to providing equal employment opportunities to all employees and applicants without regard to race, color, religion, sex, sexual orientation, gender identity or expression, national origin, disability, or veteran status. We take affirmative action to ensure that all employment decisions are based on merit, qualifications, and abilities. 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 these candidates without financial obligation to recruiters or agencies.

Requirements

Must-haves

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
• 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
• 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

Nice-to-haves

• CompTIA Network+, Security+, Microsoft MD-102, or comparable relevant certification.
• Hands-on experience with NinjaOne, HaloITSM or ManageEngine ServiceDesk Plus.
• Experience with PowerShell for troubleshooting and approved endpoint automation.
• Experience supporting a multi-site, security-conscious or regulated organization, including documented
access controls and change management.
• Exposure to endpoint security tools, Microsoft Intune, and cross-functional incident response.

Application prep

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Effort: medium

Benefits

Benefits detected in the listing.

Health Insurance

Vision

401(K)

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