Help Desk Analyst II

Position Summary:

Windward Risk Managers is seeking a proficient Help Desk Analyst II to join our IT Help Desk team. The successful candidate will work the IT support queue alongside Level 1 staff, taking on more complex tickets and serving as a point of escalation for issues that go beyond the Level 1 scope. This role is crucial in maintaining the day-to-day reliability and efficiency of our IT operations, and works closely with senior Infrastructure, Systems, and Security staff to keep end users productive and supported.

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:

• Work the IT support queue alongside Level 1 staff, responding to user requests via email, phone, and our ticketing system, while also taking on more complex tickets and escalations that require additional experience and troubleshooting depth.
• Provide remote and hands-on support across our Windows and macOS environments, including hardware troubleshooting, software installation, peripheral and printer issues, and basic network connectivity problems.
• Perform 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 employee onboarding and offboarding, including account provisioning, device preparation, software installation, and account decommissioning.
• Assist with end-user training, providing walkthroughs and guidance on company applications, tools, and IT processes for new hires and during the rollout of new systems.
• Use our RMM platform (NinjaOne) to deploy software, push patches, run remote sessions, and assist with routine endpoint maintenance.
• Monitor system reports and alerts, flagging deviations and escalating to higher-tier staff when appropriate.
• Assist with 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, helping them grow into more complex troubleshooting work.
• Maintain accurate documentation of common issues, resolutions, and changes, contributing to the IT knowledge base and asset management records.

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:

• 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 through complex tickets independently and recognize when to escalate.
• Excellent written and verbal communication skills, with the ability to explain technical issues clearly to non-technical users.
• Ability to multitask and prioritize in a fast-paced environment.
• Commitment to continuous professional development.

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.
   

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.