Help Desk Analyst II

Windward Risk; Boca Raton, Northern (FL, KY); Hybrid; USD 52,000 - 76,000; Full time

Job summary

Windward Risk Managers is seeking a proficient Help Desk Analyst II to join our IT Help Desk team in Boca Raton, FL. This in-person role supports Windows and macOS users, handles complex tickets, and escalates when needed.

You will work with Active Directory and Microsoft 365, manage onboarding/offboarding, and assist with endpoint deployments using NinjaOne. Excellent communication and troubleshooting skills are essential.

Qualifications

• Bachelor's degree or 4 years of directly related IT support experience.
• Experience with Windows and macOS, Active Directory, and Microsoft 365.
• Experience troubleshooting hardware, software, and network connectivity issues.
• Experience using RMM and remote support tools for endpoint troubleshooting and software deployment.
• Strong problem-solving and communication skills.

Responsibilities

• Work the IT support queue alongside Level 1 staff, handling basic requests and escalations as needed.
• Provide remote and hands-on support across Windows and macOS, including hardware and software issues.
• Perform AD tasks and Microsoft 365 administration such as password resets and license assignments.
• Assist with onboarding/offboarding and device provisioning.
• Document resolutions and contribute to IT knowledge base.

Skills

Windows support

macOS support

Active Directory

Microsoft 365

Hardware troubleshooting

Network connectivity

Communication skills

Multitasking

Education

Bachelor's degree or 4 years IT support experience

Tools

NinjaOne

Job description

# Help Desk Analyst IIHot JobCorporate Office - Boca Raton, FL 33487## OverviewPosition TypeFull TimeJob ShiftDayCategoryInformation Technology## Description**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## Qualifications**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.**