Help Desk Analyst II

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.

• 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.

• 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