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IT Systems Administrator Intern

Vailsys

Greater Chicago Area Hybrid internship

Posted: February 5, 2026

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Quick Summary

An IT Systems Administrator Intern will be responsible for deploying modern software and hardware solutions, supporting staff in-person and remotely, and troubleshooting issues in Vail's used technologies.

Job Description

Who You Are
Interested in being part of a Helpdesk team that deploys modern software and hardware solutions, supports and assists the staff at Vail Systems in-person and in remote locations, while working in a historic yet modern office environment located right across the river from the Chicago Lyric Opera House.

As an IT Systems Administrator Intern, you would perform security remediations and troubleshoot issues that arise in Vail used technologies. You will have the opportunity to learn and work with JAMF Pro, Jira, Office 365, exposure to Active Directory, Windows, MacOS, Linux, and other technologies.


What You’ll Do:
• Review and respond to ticket submissions in Jira
• Create and edit how-to & informational wiki articles in Confluence to help reduce the time IT System Admins spend on common, easy-to-fix issues
• Continually research up-to-date IT best practices
• Participate in knowledge-sharing exercises
• Ship, receive, recycle, and document assets using our asset inventory system
• Assist with the management of end-user systems utilizing enterprise management solutions
• Troubleshoot hardware and software errors by running diagnostics, documenting problems and resolutions, prioritizing problems, and assessing the impact of issues (Windows, MacOS, & Linux)


To be considered for this position, you must::
• Junior or Senior level student currently pursuing a Bachelor's degree in Information Systems, IT, or another related field
• Knowledge of Linux, Windows, and MacOS operating systems
• Experience with troubleshooting technical issues
• Excellent verbal and written communication skills
• Knowledge of computer hardware components


The ideal candidate will have::
• Proficiency with Office 365
• Ability to communicate with end users on a daily basis in a professional, service-oriented IT environment
• Computer-related certifications


Who We Are
At Vail, we believe in the unique power of voice interactions to create more expressive, more intimate, and more efficient interpersonal interactions. Using Vail technology, we make millions of voice interactions better every day. We process around 10% of all toll-free call traffic in the U.S.; 1 in 10 times when someone calls a customer support hotline, Vail is routing or interacting with that call.

We are rapidly growing across multiple dimensions, including our customer base, the scope of products we offer, and the size of our team. Now is the right time for a strong candidate to join and grow with us. We have a supportive culture where employees are encouraged to achieve both personal and team goals because we believe growth leads to both business impact and personal fulfillment.

We are striving to implement and sustain an inclusive and equitable work environment for all employees by sourcing underrepresented groups and continually empowering those individuals within our organization to further enrich Vail’s communication solutions. We recognize that equitable and unique individuals benefit our teams’ problem-solving, innovation, and development efforts.

Our offices are located in Deerfield and Chicago, IL. Interviews and onboarding are conducted in our offices when possible. We observe a hybrid work format that provides employees flexibility to collaborate with team members based on business needs.

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