Help Desk Analyst II (On-site) - Contract

Windward Risk Managers•Boca Raton, FL

7d•Onsite

About The Position

At Windward Risk Managers, we pride ourselves on a dynamic, supportive IT environment. Our mission is to leverage technology to enhance the efficiency and security of our operations, ensuring we continue to provide exceptional service to our policyholders and partners. We are seeking a proficient Help Desk Analyst Level 2 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. Your role is crucial in maintaining the day-to-day reliability and efficiency of our IT operations.

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 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.
Permanent U.S. work authorization.

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.