Systems Administrator II

Are you looking to make an impactful difference in your work, yourself, and your community? Why settle for just a job when you can land a career? At ICW Group, we are hiring team members who are ready to use their skills, curiosity, and drive to be part of our journey as we strive to transform the insurance carrier space. We're proud to be in business for over 50 years, and its change agents like yourself that will help us continue to deliver our mission to create the best insurance experience possible.

Headquartered in San Diego with regional offices located throughout the United States, ICW Group has been named for ten consecutive years as a Top 50 performing P&C organization offering the stability of a large, profitable and growing company combined with a focus on all things people. It's our team members who make us an employer of choice and the vibrant company we are today.

We strive to make both our internal and external communities better everyday! Learn more about why you want to be here!

The purpose of the Systems Administrator II is to ensure that ICW Group’s computing environment and infrastructure technologies are properly administered and maintained in support of the company’s computer operations. This role exists to define procedures for monitoring, evaluating, diagnosing and establishing a work plan to resolve system issues.

Administers, maintains and upgrades computing systems.

• Deploys and installs new software releases and system upgrades.
• Evaluates and installs patches and resolves software related problems.
• Implements, and administers Microsoft Power Platform solutions, including Power Automate, Power Apps, and Power BI, to enable workflow automation, application development, and data-driven insights across the organization.
• Designs and implements AI-driven automation and AIOps solutions to improve system reliability, operational efficiency, and service quality.
• Develops and maintains automation workflows and scripts (e.g., Power Shell, Python, Ansible, Power Automate) to support provisioning, configuration, patching, and routine operational tasks.
• Leverages AI and analytics for proactive monitoring, anomaly detection, event correlation, automated incident response and root cause analysis.
• Monitors and reports on automation effectiveness using operational metrics (e.g., incident reduction, MTTR improvement, productivity gains) and evaluates emerging AI technologies for operational value.
• Performs system backups and recovery.
• Maintains and monitors system configuration.
• Provides 2nd and 3rd Tier technical support and problem resolution.
• Implements and maintains current and future ICW Group computing technologies.
• Administers the maintenance of account management processes using Active Directory, LAN based user application systems, enterprise messaging and collaboration technologies, and enterprise data storage environment where applicable.

Defines procedures for monitoring, evaluating, diagnosing, and establishing a work plan to resolve system issues.

• Assists in the research, development, and testing of new computing technologies in support of ICW Group business operations.
• Implements and maintains Configuration Management practices and documentation for all hardware, operating systems, and application software systems.
• Maintains a systems business impact assessment to be used for emergency recovery purposes.

Troubleshoots and supports internal teams.

• Maintains system documentation.
• Applies revisions to host system firmware and software.
• Partners with business and other IT teams to implement a systems business impact assessment.

This role does not have supervisory responsibilities.

• Bachelor's degree preferred in Computer Science, Information Systems, or related field.
• Minimum 5 years of related experience; or equivalent combination of education and experience required.
• Experience in a M365 Sharepoint Online environment required. A365 “Agentic” experience preferred.

Current Microsoft MCSE certification.

• Demonstrates strong problem-solving…