Chicago - IT Operations Engineer

Winston Taylor; Chicago (IL); On-site; USD 115,000 - 130,000; Full time

Benefits offered by this job

Comprehensive healthcare benefits

Yearly retirement contribution

Annual discretionary merit bonus

Job summary

Winston Taylor is seeking an IT Operations Specialist to support a complex enterprise IT environment in Chicago, IL. The candidate will leverage PowerShell for automation, manage network/application monitoring, and provide tier three incident support.

This role requires 3+ years in IT operations, technical expertise in Microsoft and Cisco technologies, and the ability to document procedures in an ITSM platform. A strong benefits package is offered with a competitive salary range of $115,000-$130,000.

Qualifications

• 3+ years in IT operations with ITSM platforms experience.
• Knowledge of LAN and WAN terminologies, technologies, and topologies.
• Experience in documenting all work in an ITSM platform.

Responsibilities

• Run automation of operational activities utilizing PowerShell and ActiveRoles Server.
• Provide tier three incident service request and problem management support.
• Administer and maintain Operations platforms including identity and SaaS.

Skills

IT operations

Troubleshooting

Network monitoring

Automation with PowerShell

Scripting languages

Education

Associate's degree

Bachelor's degree

Tools

Microsoft technologies

Cisco

VMWare

Job description

About Us

At Winston Taylor, we set the standard, together. Winston Taylor is a transatlantic law firm built for the businesses, people, and markets driving capital and innovation. Here, you’re in the room. In the action. Sleeves rolled up. You’ll work with leading clients, disruptors, and fast‑growth companies, helping them stay one step ahead of the moment and make critical decisions that shape their future. We’re present in the U.S., U.K., Europe, Latin America, and the Middle East, combining the scale and speed that clients demand. You’ll be trusted with real responsibility from the outset and build experience through hands‑on work. We take your progression personally. We provide the platform. You shape the work around your goals and aspirations. Step into the moments that matter. Join Winston Taylor.

Position Summary

Responsible for automation, administration, and operational support of a complex enterprise IT environment, including identity and access management, network and application monitoring, email and spam filtering, SaaS platforms, file and print services, and secure file transfer systems. Leverages PowerShell and Active Roles to automate operational workflows, provides tier three incident, service request and problem management support, and partners cross‑functionally to improve monitoring, reliability, and compliance with security and operational standards.

Position Responsibilities

• Network / Application Monitoring and Triage.
• Run automation of operational activities utilizing PowerShell, ActiveRoles Server, etc.
• Assist in developing integrations of new IT projects into Operational Support Processes.
• Act as liaison with Identity, Collaboration, Infrastructure and Application teams to enhance monitoring, identify recurring issues, propose process enhancements while maintaining ownership through the process.
• Provide tier three incident service request and problem management support to Technical Support teams. Work with appropriate engineers, support personnel, and vendors to resolve issues accurately and within reasonable time limits.
• Administer, maintain, and support Operations platforms including but not limited to monitoring, two‑factor authentication, printing, identity, SaaS, automation, collaboration, networking and Infrastructure.
• Perform system administration procedures, adhering to Winston and IS network and security policies, procedures and standards.
• Provide weekend and after‑hours support as required by the position.
• Responsible for basic email administration and troubleshooting including but not limited to spam, virus filtering, and message tracking.
• Provision network and application user accounts including network login, email, document management, fax, file transfer, etc.

Experience, Skills, and Qualifications

• Associate’s degree required. Bachelor’s degree preferred.
• 3+ years in IT operations with experience working with ITSM platforms required.
• Experience with a variety of technical systems, including Microsoft technologies, Cisco, Meraki, VMWare required.
• Must live within a commutable distance to a firm office with the ability to come into the office 3-4 days per week.
• Network / Application monitoring and troubleshooting experience in an Enterprise IT environment.
• Experience in documenting all work in an ITSM platform.
• Experience implementing best practices in the “run” phase of IT systems.
• Knowledge of LAN and WAN terminologies, technologies and topologies.
• Knowledge of Internet Service Providers with troubleshooting.
• Microsoft and/or Cisco certifications preferred.
• Azure, AD, Entra and M365 administration experience.
• Prior experience with scripting languages and APIs.
• Ability to manage large workloads, while producing quality work in a fast‑paced environment with interruptions, deadlines and context switching.
• Top‑notch analytical skills; methodical and detail‑oriented, planner and problem‑solver; ability to eliminate variables, prioritize requirements, identify root causes and present objective, organized information to customers, internal and external partners.
• Accessibility outside normal business hours when required.

Benefits

Winston offers comprehensive benefits that provide a full spectrum of coverage and support for our full‑time employees and their families. Additional information about benefits and rewards can be found here.

SALARY

Illinois applicants only: The target annual salary range for this role is currently $115,000-$130,000 based on a regular, full‑time schedule. The amount of compensation offered will be determined by several factors, including but not limited to experience, qualifications, market data and internal equity. Total compensation includes a comprehensive healthcare benefits package, yearly retirement contribution, and may include an annual discretionary merit bonus.

We are an equal opportunity employer and welcome applicants from all backgrounds and experiences.