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Agent guide: [/agents.md](https://www.wearedevelopers.com/agents.md). --- # Help Desk Analyst II - **Company:** Windward Risk Managers - **Location:** Boca Raton, FL, United States - **Experience:** Experienced - **Contract:** Permanent contract - **Skills:** Microsoft Windows, Active Directory, Apple Mac Systems, Issue Tracking Systems, Information Technology Operations, Remote Service Software, Software Deployment, Connectivity Problems, Information Technology, User Administration - **Published:** September 23, 2026 - **Apply:** https://www.indeed.com/viewjob?jk=fb9daa2ee7d7fbc8 ## About the Role * 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., * 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. ## Description 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 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. ## Related Videos - [SwiftUI In Production](https://www.wearedevelopers.com/videos/134-swiftui-in-production) - [Fake or News: Translating Dog Barks, Notepad Gets an Upgrade and Michelin-Star Robots - Paul Tregoing](https://www.wearedevelopers.com/videos/1802-fake-or-news-translating-dog-barks-notepad-gets-an-upgrade-and-michelin-star-robots-paul-tregoing) - [MCP Mashups: How AI Agents are Reviving the Programmable Web](https://www.wearedevelopers.com/videos/1392-mcp-mashups-how-ai-agents-are-reviving-the-programmable-web) - [Checkmate: 5 Real Incidents That Can End a Software Company](https://www.wearedevelopers.com/videos/100126-checkmate-5-real-incidents-that-can-end-a-software-company) - [How Lufthansa Industry Solutions is preparing for the Quantum Age! ](https://www.wearedevelopers.com/videos/1443-how-lufthansa-industry-solutions-is-preparing-for-the-quantum-age) - [What makes Cybersecurity different for critical infrastructure?](https://www.wearedevelopers.com/videos/571-what-makes-cybersecurity-different-for-critical-infrastructure) ## Related Articles - [Fully Remote Software Engineer Jobs](https://www.wearedevelopers.com/magazine/447-fully-remote-software-engineer-jobs) - [The Best Job Search Websites of 2025](https://www.wearedevelopers.com/magazine/368-the-best-job-search-websites-of-2025) - [The Most Popular IT Jobs on the Market](https://www.wearedevelopers.com/magazine/376-the-most-popular-it-jobs-on-the-market) - [Data Analyst Salary in the UK](https://www.wearedevelopers.com/magazine/278-data-analyst-salary-in-the-uk) - [Best Job Boards for Remote Work for Developers](https://www.wearedevelopers.com/magazine/290-best-job-boards-for-remote-work-for-developers) - [Is Software Engineering Over-Saturated?](https://www.wearedevelopers.com/magazine/418-is-software-engineering-over-saturated)