Senior IT Service Desk Technician

Old Republic Risk Management (ORRM) is seeking a Senior IT Service Technician to join our team in Brookfield, Wisconsin. In this role, you will serve as a key resource for IT support, helping employees resolve technical issues, maintain critical systems, and ensure a seamless technology experience across the organization., * Providing technical support to employees via phone and email

• Troubleshooting hardware, software, and network issues
• Setting up and deploying new workstations and devices
• Managing user access and account administration
• Supporting Microsoft 365 applications and Exchange environments
• Maintaining system performance and technology standards

Once fully trained, this position offers a hybrid work schedule with the flexibility to work remotely two days per week. Additional responsibilities include:

• Managing systems management tools and appliances
• Analyzing support trends and identifying improvement opportunities
• Maintaining software and hardware inventories
• Supporting employee onboarding and technology setup
• Creating and maintaining technical documentation and procedures

Do you have experience in Windows?, Do you have a Associate’s degree?, * Associate’s or higher degree in IT, Computer Science, or a related field, and a minimum of four years of progressively responsible experience performing similar duties; an equivalent combination of education, training, and experience would also be considered in lieu of a formal degree.

• Experience supporting Windows operating systems, printers, and mobile devices
• Strong troubleshooting and problem-solving skills
• Ability to work effectively in a fast-paced environment
• Excellent communication and customer service skills
• Commitment to delivering high-quality technical support

We’re looking for someone who enjoys solving technical challenges, helping others succeed, and delivering exceptional service across the organization.

Pulled from the full job description

• Referral program
• Pet insurance
• Health insurance
• 401(k) matching
• Paid time off
• Vision insurance

• Health savings account, * Expected Salary Range: $80,000 - $90,000 annually. Actual compensation will be determined based on factors such as experience, skills, education, certifications, internal equity, and market conditions.

• 401(k) with company match and profit-sharing
• Roth and 529 Education Savings Plans
• Employee referral bonus program

Health & Wellness

• Medical, dental, vision, and life insurance
• Health Savings Account (HSA) and Flexible Spending Account (FSA) options
• Long-term disability and critical illness coverage
• Pet insurance

Work-Life Balance

• 37.5-hour standard workweek
• Hybrid work flexibility
• Generous paid time off and company holidays
• Volunteer opportunities
• Casual business attire
• Company-sponsored events and team activities

About Old Republic Risk Management

Old Republic Risk Management serves the casualty insurance and risk management needs of large corporate and group clients across industries that are vital to the North American economy. As a pioneer in alternative market approaches to insurance risk management, ORRM has partnered with Fortune 500 companies and other major enterprises since the 1950s. Our expertise includes innovative risk financing solutions such as:

• Large deductible programs
• Self-insurance structures
• Captive insurance arrangements

Why Join ORRM?

We are committed to attracting and developing talented professionals who share our values and dedication to excellence. ORRM offers a collaborative, open-door environment where teamwork, professional growth, and individual contributions are recognized and valued.