Help Desk Analyst II

Windward Risk Managers is seeking a Help Desk Analyst II to strengthen its IT support operations from the help desk queue through escalation and hands-on troubleshooting. In this role, you’ll partner with Level 1 analysts while owning more complex issues, providing support across both Windows and macOS environments, and helping maintain accurate service documentation. The position is based on-site in Boca Raton, FL.

Role overview

As a second-level analyst, you will respond to user requests through the ticketing system and other support channels, acting as an escalation point for problems that require deeper troubleshooting. You’ll also manage endpoint maintenance and deployments using NinjaOne, support account and access tasks in Active Directory and Microsoft 365, and assist with onboarding, offboarding, and small IT rollouts under the direction of senior staff.

Responsibilities

• Work the IT support queue alongside Level 1 staff, handling requests by email, phone, and ticketing system, and taking on complex tickets and escalations when additional experience is required.
• Deliver remote and hands-on support for Windows and macOS, including hardware troubleshooting, software installation, peripheral and printer issues, and basic network connectivity problems.
• Manage user account and access tasks in Active Directory and Microsoft 365, including password resets, account creation, group membership changes, mailbox configuration, and license assignments.
• Support onboarding and offboarding activities, including account provisioning, device preparation, software installation, and account decommissioning.
• Assist with end-user training by providing walkthroughs and guidance on company applications, tools, and IT processes for new hires and during system rollouts.
• Use NinjaOne to deploy software, push patches, run remote sessions, and support routine endpoint maintenance.
• Monitor system reports and alerts, flag deviations, and escalate to higher-tier staff when appropriate.
• Support small IT projects and rollouts, such as hardware refreshes and software deployments, under the direction of senior staff.
• Provide guidance and knowledge sharing to Level 1 analysts to support growth into more complex troubleshooting.
• Maintain accurate documentation of common issues, resolutions, and changes for the IT knowledge base and asset management records.

Requirements

• Bachelor’s degree or 4 years of directly related IT support experience.
• Working knowledge of Windows and macOS support, Active Directory, and Microsoft 365.
• Experience troubleshooting hardware, software, and network connectivity issues across desktop and laptop environments.
• Comfort using RMM and remote support tools for endpoint troubleshooting and software deployment.
• Strong problem-solving skills, with the ability to work independently on complex tickets and recognize when to escalate.
• Excellent written and verbal communication skills, including the ability to explain technical issues to non-technical users.
• Ability to multitask and prioritize in a fast-paced environment.
• Commitment to continuous professional development.

Technologies

• Windows
• macOS
• Active Directory
• Microsoft 365
• NinjaOne

Benefits

• 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
• Dental insurance
• Employee assistance program
• Health insurance
• Life insurance
• Paid time off
• Parental leave
• Referral program
• Vision insurance

Preferred qualifications

• CompTIA A+, Network+, or equivalent IT support certification
• Microsoft 365 Certified: Modern Desktop Administrator Associate (MD-102) or Microsoft 365 Fundamentals (MS-900)
• Hands-on experience with NinjaOne or a comparable RMM platform
• Experience supporting users in a multi-site environment and prior experience mentoring Level 1 analysts

Notice to third party agencies: WRM does not accept unsolicited resumes from third party recruiting firms.