Senior Help Desk Analyst: Endpoint Expert & Mentor

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

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.