IT Operations Support Supervisor

IT Operations Support Supervisor

Location:

Brookfield, WI (Onsite; hybrid schedule with two remote days per week after training. This position is primarily onsite and not fully remote.)

About the Company

Old Republic Risk Management (ORRM) serves the casualty needs of large corporate and group clients across industries that power the North American economy. As a pioneer of the alternative market approach to insurance risk management, ORRM has partnered with Fortune 500 companies and major public and private enterprises since the early 1950s. Through our unbundled claims and risk control model, we deliver innovative, flexible solutions including large deductibles, self-insurance, and captive mechanisms. Known for best-in-class service, responsiveness, and product stability, Old Republic Risk Management continues to drive profitable growth by building on the strength of our core expertise and long-standing client relationships.

Duties

The IT Operations Support Supervisor leads and develops IT service desk staff while overseeing day-to-day support operations. This role supervises team members through training, coaching, performance management, and participation in recruitment, hiring, and onboarding. The IT Operations Support Supervisor prioritizes and distributes workload to ensure timely resolution of incidents and service requests, while serving as the primary escalation point for complex technical issues. With strong hands-on expertise, including M365 Administration, this leader provides direct support and guidance to ensure effective problem resolution.

This position analyzes trends and recurring incidents to identify root causes and implement corrective actions that improve service delivery and reduce repeat issues. The IT Operations Support Supervisor develops and enhances standard operating procedures and process documentation to drive consistency and continuous improvement. By establishing clear performance goals and monitoring service desk metrics, this role promotes accountability, removes operational obstacles, and elevates the user experience. The IT Operations Support Supervisor also oversees conference room and collaboration technology support, ensuring reliable and seamless technology performance throughout the organization. This position also requires availability for on-call support, including evenings and weekends, to address system emergencies and ensure business continuity.

Experience & Education

An Associate's or Bachelor's degree is required with a minimum of two years of related experience, including proficiency in M365 Administration. In lieu of a degree, five years of related experience, including M365 Administration, is required. Prior supervisory experience is preferred. Candidates should demonstrate strong leadership capabilities, technical problem-solving skills, and the ability to drive operational excellence in a fast-paced environment.

Benefits

Financial & Retirement:

• Competitive Salary

• 401(k) Savings & Profit-Sharing Plan with company match

• Roth investment options

• 529 Education Savings Plan

• Employee Referral Bonus Program

Health & Insurance:

• Health Insurance

• Dental Insurance

• Vision Insurance

• Flexible Spending Account (FSA) & Health Savings Account (HSA) options

• Life Insurance & Supplemental Life Insurance

• Long-Term Disability Insurance

• Accident & Critical Illness Insurance

• Pet Insurance

• Paid Leave of Absence Benefits

Work-Life Balance & Culture:

• 37.5-hour standard work week

• Hybrid work opportunities available upon completion of training

• Casual business attire

• Generous paid time-off (PTO)

• Paid holidays

• Volunteer opportunities

• Company-sponsored events and outings

If you are a driven IT leader ready to elevate service excellence and make a meaningful impact within a respected, industry-leading organization, we encourage you to apply today. Join Old Republic Risk Management and take the next step in advancing your leadership career as our IT Operations Support Supervisor.

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Old Republic Risk Management is an Equal Opportunity Employer and is committed to maintaining a diverse workplace.