Help Desk Analyst II – Escalations & Remote OS Support

Windward Risk Managers; Boca Raton (FL); On-site; USD 52,000 - 68,000; Full time

Job summary

Windward Risk Managers is seeking a proficient Help Desk Analyst II to support Windows and macOS environments, manage user accounts in AD and Microsoft 365, and assist with onboarding and training. You will work closely with senior staff to resolve complex tickets and improve IT operations.

The role emphasizes hands-on troubleshooting, remote sessions, documentation, and escalation to higher-tier teams as needed. On-site Florida location.

Qualifications

• Bachelor's degree or 4 years of IT support experience is required.
• Experience supporting Windows and macOS, AD and Microsoft 365 is essential.
• Strong problem solving and communication skills are required.

Responsibilities

• Handle IT support queue with Level 1 staff and escalate complex tickets.
• Provide remote and on-site support for Windows and macOS devices.
• Perform Active Directory and Microsoft 365 user tasks and provisioning.
• Assist with onboarding/offboarding and device prep.
• Maintain documentation and contribute to the knowledge base.
• Utilize NinjaOne to deploy software and patches, run remote sessions.

Skills

Windows support

macOS support

Active Directory

Microsoft 365

Password resets

Education

Bachelor's degree or 4 years IT support experience

Tools

NinjaOne

RMM tools

Job description

Windward Risk Managers is seeking a proficient Help Desk Analyst II to support Windows and macOS environments, manage user accounts in AD and Microsoft 365, and assist with onboarding and training. You will work closely with senior staff to resolve complex tickets and improve IT operations.

The role emphasizes hands-on troubleshooting, remote sessions, documentation, and escalation to higher-tier teams as needed. On-site Florida location.