IT Operations Specialist

The IT Operations Specialist keeps We Insure’s cloud systems and applications running reliably while giving employees fast, dependable technical support. This role splits its time evenly between cloud operations and front-line user support, with the remainder spent on documentation, process improvement, and department initiatives. Network hardware work is limited to on-site “smart hands” tasks (physical installs, cabling, and swaps) performed under the direction of the network/security team, not network design or administration. It’s a strong fit for someone who enjoys variety and takes ownership of problems until they’re actually resolved., Cloud Systems & Operations

• Support, monitor, and maintain cloud-hosted applications and platforms (e.g., Microsoft 365, Entra ID, Intune, Azure/SaaS environments), keeping updates, patching, backups, and scheduled tasks running as expected and proactively optimized.
• Configure and administer cloud-based systems, identity/authorization platforms, and SaaS applications according to established standards.
• Support Entra ID and other cloud identity and authorization systems.
• Monitor and analyze cloud system performance and availability, using management and logging tools to catch issues before they become outages.
• Troubleshoot hardware and software malfunctions to minimize downtime and service disruption.
• Maintain accurate records in the change management system for all systems changes.
• Support the deployment, tracking, and retirement of IT hardware assets (endpoints, peripherals, and office equipment).
• Serve as on-site “smart hands” for network equipment, physically installing, cabling, swapping, or power-cycling switches, access points, and firewalls under the direction of the network/security team.
• Identify opportunities to improve the cloud IT environment and flag security risks or potential service disruptions to the team.

User Support & Service Delivery

• Serve as first- and second-level contact for IT support requests, resolving issues promptly and professionally.
• Diagnose and repair hardware, software, and peripheral issues for end users.
• Manage user access rights and accounts within the identity management system, following corporate security and data-integrity standards.
• Install, test, and upgrade software to keep it current, compatible, and efficiently deployed.
• Support the rollout of corporate IT projects, including planned phase-outs and transitions.
• Provide user training and practical guidance on equipment and software to help employees work more effectively.
• Log hardware/software issues, actions, and resolutions in the ticketing system to build a reliable reference for recurring problems.
• Partner with application vendors and internal stakeholders to resolve issues and improve the overall user experience.

Documentation, Process & Special Projects

• Create and maintain systems documentation, including technical manuals, network/security diagrams, project requirements, and project plans.
• Provide timely status updates to management on assigned special projects.
• Help develop and refine IT support standards, procedures, and best practices.
• Review systems periodically to confirm they’re implemented and maintained per policy.
• Deliver individual and group training sessions as needed.
• Support disaster recovery and business continuity planning to reduce operational risk.
• Assist management with technology evaluations and vendor comparisons.
• Cross-cover for other IT team members and support contracted operations partners as needed.

• 3-5 years of relevant experience in IT operations, cloud administration, or help desk support.
• Working knowledge of IT security principles, best practices, and tools used to protect end-user devices and cloud data.
• Hands-on experience administering and supporting cloud platforms and SaaS applications (e.g., Microsoft 365, Entra ID, Intune, or similar).
• Comfort performing basic physical (“smart hands”) tasks on network hardware, racking, cabling, swapping, or rebooting equipment without requiring network engineering or configuration expertise.
• Experience applying IT security best practices in a cloud environment.
• Experience gathering and analyzing client/user requirements and recommending practical options.
• Comfort working with centralized cloud IT system management tools.
• Strong interpersonal and communication skills, with the analytical and troubleshooting instincts to see problems through to resolution.
• Careful attention to detail, particularly around documentation, access management, and change control.

Preferred

• Experience supporting a multi-location or franchise organization.
• Familiarity with Microsoft 365, Entra ID, Intune, and other cloud/SaaS endpoint management tools.
• Exposure to ITSM/ticketing platforms (e.g., Jira Service Management) and change management workflows.
• Relevant certifications such as CompTIA A+/Cloud+/Security+, Microsoft (MS-900, AZ-900), or similar.

At We Insure Group, we are passionate, driven, and purposeful in our mission to personalize protection at the right value. We believe in delivering tailored insurance solutions that meet each client’s unique needs, ensuring they feel confident and supported in every decision.

As both a franchise platform and direct insurance provider, We Insure empowers like-minded entrepreneurs with the opportunity to own and operate successful agencies. With over 200 locations across 35 states, we support our agency owners, customers, and carrier partners by enabling faster service, greater efficiency, better choices, and improved results.

What sets us apart? We’re data-driven for better value and people led for better service. Our purpose is rooted in clarity, guidance, and long-term trust helping individuals and business owners make informed choices about their insurance coverage. We’re building something meaningful and looking for purpose-driven individuals to help lead the way.