Help Desk Analyst III (Contract)

Windward Risk Managers; Boca Raton (FL); On-site; USD 75,000 - 95,000; Full time

Benefits offered by this job

401(k) matching

Dental insurance

Employee assistance program

Health insurance

Life insurance

Paid time off

Parental leave

Referral program

Tuition reimbursement

Vision insurance

Job summary

Windward Risk Managers seeks an experienced Help Desk Analyst III to act as a senior technical resource in IT Help Desk onsite at Boca Raton. This hands-on role handles complex incidents escalations beyond Level1, mentors junior staff, and partners with Infrastructure, Systems, Network, and Security teams.

You will own onboarding/offboarding, device lifecycles, and contribute to endpoint management and technology rollouts while maintaining responsive end-user support.

Qualifications

• 5+ years of progressive hands-on IT support experience with Level 2/3 escalations.
• Strong knowledge of Windows endpoint support and Microsoft 365.
• Experience with Active Directory and Microsoft Entra ID management.
• Proficient in DNS/DHCP/TCP/IP and VPN troubleshooting.
• Experience with ITSM ticketing and endpoint lifecycle management.

Responsibilities

• Own and resolve advanced Level 2 escalations and complex Level 3 incidents; coordinate with specialist teams when infrastructure changes are required.
• Provide expert remote and onsite support for Windows 11 and macOS endpoints; address OS failures, conflicts, performance and encryption issues.
• Troubleshoot Microsoft 365 and Exchange Online issues including Outlook, Teams, OneDrive, permissions and licensing.
• Perform advanced Active Directory and Microsoft Entra ID account and access troubleshooting; follow change procedures.
• Diagnose network and remote access issues using DNS, DHCP, TCP/IP, VPN; collaborate with Network/Security teams.
• Lead onboarding/offboarding, device replacement, reimaging and lifecycle tasks; ensure accurate asset records.
• Mentor Level 1/2 analysts; maintain SOPs, tickets, knowledge articles; support system migrations and deployments.
• Communicate clearly with end users and cross-functional teams during high-priority incidents.

Skills

Windows endpoint support

Microsoft 365

Exchange Online

Active Directory

Microsoft Entra ID

DNS

DHCP

TCP/IP

VPN

RMM platforms

Remote support

ITSM ticketing

PowerShell

Endpoint automation

NinjaOne

HaloITSM

ManageEngine ServiceDesk Plus

Education

CompTIA Network+

Security+

Microsoft MD-102

Tools

NinjaOne

HaloITSM

ManageEngine ServiceDesk Plus

PowerShell

Job description

POSITION SUMMARY:Windward Risk Managers is seeking an experienced Help Desk Analyst III to serve as a senior technicalresource within the IT Help Desk. This hands-on position handles complex incidents and escalations thatexceed Level 1 and Level 2 capabilities, independently drives issues through resolution, and partners withInfrastructure, Systems, Network, and Security teams on advanced troubleshooting. The successful candidatewill also mentor junior technicians, strengthen documentation and operational standards, and contribute toendpoint 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-causeanalysis, document findings, and coordinate with specialist teams when infrastructure-level changes arerequired.• Provide expert remote and onsite support for Windows 11 and macOS endpoints, including recurringoperating system failures, application conflicts, device performance, encryption, driver and peripheralissues.• Troubleshoot Microsoft 365 and Exchange Online issues involving Outlook, Teams, OneDrive, sharedmailboxes, permissions, licensing, authentication, and user productivity.• Perform advanced Active Directory and Microsoft Entra ID account, group, access and identitytroubleshooting; follow approved access controls and change procedures.• Diagnose client-side network and remote access issues using DNS, DHCP, TCP/IP, Wi-Fi and VPNtroubleshooting; collaborate with Network and Security teams on upstream causes.• Use NinjaOne and other approved remote management tools to investigate endpoint health, deploysoftware, execute vetted scripts, support patch remediation, and improve endpoint consistency.• Lead technically complex onboarding, offboarding, device replacement, reimaging and hardware lifecycletasks, 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 knowledgetransfer; 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 duringhigh-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 companies100% employer paid health insurance for employeesUp to 6% 401(k) match with immediate vestingLong-term and short-term disability insurance3 weeks PTO to start + generous paid holidaysTuition reimbursement and continuing education supportCollaborative and growth focused cultureREQUIRED QUALIFICATIONS:• At least 5 years of progressive hands-on IT support experience, including substantial Level 2troubleshooting and demonstrated ownership of senior-level escalations; equivalent relevant experiencewill be considered.• Strong practical knowledge of Windows endpoint support, Microsoft 365, Exchange Online, ActiveDirectory and Microsoft Entra ID.• Demonstrated ability to independently diagnose complex hardware, software, identity, connectivity andendpoint 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 lifecyclemanagement.• Experience using an ITSM ticketing platform and maintaining thorough, audit-ready ticket documentation.• Strong judgment, prioritization, customer service, communication and mentoring skills; ability to workeffectively 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 documentedaccess 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 remainsactively 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.Benefits:* 401(k) matching* Dental insurance* Employee assistance program* Health insurance* Life insurance* Paid time off* Parental leave* Referral program* Tuition reimbursement* Vision insurance