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Headquarters: 190 S. LaSalle St., Suite 3800 | Chicago, IL 60603-3432

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IT Resident Intern (Remote: Summer 2021)

(View all jobs)

Wanted: A Techno-Padawan seeking Galactic exposure

(Also known as an IT Resident Intern)



We invite you to join Entara and start your journey as an IT Resident Intern. This fast-tracked, internship program is where many EntaraCorps began their career progression into both technical and even some non-technical positions that influence our clients lives on a daily basis.

At Entara, we believe in “always learning” employees—engineers at all levels who value personal advancement and want to escalate up the skills ladder. We do our best to make that happen. You won’t find yourself on the hamster wheel at Entara; we don’t waste time fixing the same issues over and over—we seek to move ourselves and our clients, beyond into the future of technological advances.

There are no “McJobs” at Entara. Our senior engineers are required to teach and mentor residents, not just supervise them. As a resident, you’ll be responsible for solving a wide variety of network and systems issues for Entara’s clients. When you need support, it’s immediately available. You’ll be learning by doing.

We call this internship experience a “residency” because it’s an opportunity to enhance your skills with hands-on experience solving problems for businesses of all shapes and sizes. You’ll be using a variety of IT tools and products. You’ll deal with services for client accounts but also be exposed to customized IT systems and networks.

A residency at Entara isn’t limited to technology. Our success is built on relationships with co-workers, end-users, clients and their clients and employees. Because we’re a small firm, with a philosophy of teamwork and transparency, you’ll also learn how the business operates.

We created this unique residency because we are seeking the best and brightest individuals to join our team. Of course, we hope you find your home at Entara and choose to stay. But even if you don’t, an Entara residency will prepare you for a lifelong, successful IT career in a way that any other internship just simply cannot match.


(Otherwise known as the fine print, the list of job tasks and responsibilities.)

IT Resident Interns are exposed to the entirety of Entara’s services landscape. Interns are responsible for solving a variety of client user issues, everything from providing first-level support for desktop, network, and system issues facing Entara’s clients to assisting Entara Engineers with project tasks ranging from breach remediation to internal improvement measures. Resident Interns are exposed to a variety of environments in the mid-size marketplace and gain hands-on, trial by fire experiences with end-user troubleshooting, monitoring and management tools, and IT operational best practices through working alongside both our Engineer Resident and Sr. Engineer teams during their time as an intern.

Given the unpredictable health landscape, IT Resident Interns are expected to be offered in both a remote and hybrid (remote and onsite) capacity for Summer 2021.

IT Resident Interns are expected to:

  • Gain valuable hands-on experience at a fast-paced IT Managed Service Provider
      • Understand Entara’s Ticketing Systems & Documentation
      • Receive training on troubleshooting best practices and employed, ITIL methodologies
      • Apply and polish the fundamentals of customer service: how to handle client interactions & assess priority
      • Flex into multiple service teams: fighting fires within managed services and conquering mountainous tasks within professional services, resulting in an immersive summer experience
      • Receive training on procedures, processes, and operations in Entara’s combined NOC & Service Desk, otherwise known as the “Command Center”
  • Carry Out Operations
    • Be available and logged into support queues and required tools
    • Accept cases from the support queue
    • Be the first point of contact for all issues and triage appropriately
    • Follow Entara’s internal core processes affecting time entry standards, required follow-ups, and thorough documentation of the issue at hand
    • Assist clients with support, both onsite (as available) and remotely
    • Communicate progress on problems, as well as resolution
    • Exceed SLA guarantees to Entara’s clients
    • Document all tasks in ITSM platform
    • Know when to fold ‘em—understand when and how to escalate an issue
    • Work with network and systems engineers to maintain our internal network and address internal IT support issues
  • Dive into “the checklist” for speedy remediation
    • Flex into the breach remediation project team during seasons of high activity
    • Gain insight into the after-math of a security breach and the tasks that are required to get an organization up and operational.
    • Complete daily assigned tasks in a fast-paced, team setting: i.e. reimaging a server, restoring from backups, to rebuilding a VMWare environment.
  • Apply Learned Skills to Employ Technology
    • Complete new computer setups including full-workstation builds
    • Fix virus/malware issues
    • Configure network printers
    • Resolve computer application and operating system issues
      • Install, configure, and troubleshoot workstation and network hardware
      • Verify network connectivity, both wired and wireless
      • Provide mobile device support, including Apple, Android, and Windows devices
    • Manage end-user email experience
      • Master Exchange and Office365
      • Troubleshoot bounce-backs, SPAM, and transmission issues
      • Configure webmail
    • Manage user profiles
      • Navigate Active Directory and Exchange to perform password resets, move/add/change requests, file permission adjustments, and distribution list creation


  • You are actively working towards completion of your Bachelor’s degree in a technology centric major OR you are an active at-home technical tinker-er seeking to turn pro. Regardless of how you caught the IT bug, you are seeking an opportunity to put your current knowledge into action and gain valuable exposure to a corporate IT environment!
  • You have a dedicated, private space for a home office and already have in place a reliable, private internet connection with at least 25MBPS bandwidth. Public wifi and shared common spaces do not meet these standards. Entara will supply you with a laptop and the other necessary tools and hardware to complete your tasks remotely.
  • You are available for a remote or hybrid (remote & onsite) full-time internship opportunity spanning 10-14 weeks in Summer 2021.
  • You are fascinated by the technical industry and want to continue to gain exposure to (and be a valuable part of) the internal operations of one of Chicago’s Best Managed Service Providers!
  • You have a desire to become the grease monkey of the IT environment and are currently considered your family’s “techie-troubleshooter”. You have a solid understanding of desktop hardware and operating systems, and can use hardware diagnostic tools to address operating systems issues. You have a solid understanding of standard employee productivity suites—Microsoft Office/Outlook, and you have basic understanding of mobile device configurations and support.
  • You have foundational exposure to and more ideally, lab experience working with servers and networking equipment in both a virtual and physical capacity.
  • At the end of a long day, you pride yourself on the influence you had on another person’s day. It’s not just about the technical feat, but about being that go-person that others want to have solve their issue time and time again.


  • Right Brain, Left Brain OS: You’re a little bit of a fanatic when it comes to correctly implementing known solutions, but you’ve got a streak of Potter-ish ingenuity when something weird comes along. You break problems down, using a logical process of elimination to solve them. But you pay attention to intuitive inspiration.
  • Persnickety: You follow complex, detailed instructions for complex, detailed tasks. Again, you avoid even thinking, “That’s good enough.”
  • Bilingual in English and Tech-speak. You understand what the problem is, even when the person calling is 404, technically speaking. While they’re talking, you’re thinking technologically, assessing and solving their issue, then translating the solution into English before communicating it to the end-user. In other words, you speak the mainstream language recognized by Muggles.
  • Resilience of a rubber band: You don’t snap when stretched to your limits by panicked, frustrated and/or irate users who probably tried to solve the problem themselves before and are now operating on their last nerve. You have the temperament of a Zen monk on a Rocky Mountain high.
  • Appetite for learning: You’re always reaching for the next apple on the knowledge tree, as well as the last piece of pizza in the box. Learning is its own reward—but it also helps when you have your eye on a job in the next tier. With 98% of Entara interns receiving full-time offers after their residency, that next step could be closer than you think. You like working in a managed-knowledge organization that promotes from within as you gain experience.
  • Persistent, but not stubborn: You’ll be damned if you’re going to give up on a problem you know you can solve, but you recognize when it’s time to escalate to a higher tier. Next time, you’ll have the solution at hand.
  • You play fair. You live by all those early childhood lessons about treating people with respect, keeping your commitments, listening to the views of others, resolving conflict through negotiation, communicating clearly, and contributing to a positive team effort. You place team success above your individual interests.

We’re serious about these qualities. If they don’t apply to you, you won’t be happy at Entara and we won’t be happy with you. We’ll part ways sooner rather than later.  Let’s avoid all that discomfort by agreeing you won’t contort yourself to meet requirements that just don’t fit. You are who you are, and that’s okay.


Entara is a new kind of IT Managed Services Company. We’re built from the ground up to provide the strategic vision, platforms, processes and people to travel with our clients on the path to their best IT future. We partner with mid-sized Chicago organizations to make technology work brilliantly for our clients.

We launched in 2001, as the niche firm YJT Solutions (You Just Trade) helping to solve some of the IT challenges of Chicago’s most intense trading environments. Because of our success working in the financial industry, we branched out to serve other industries over a decade ago.

In 2018, we rebranded to Entara because our company has grown and evolved far beyond its original roots. We are doubling down on making investments in our future to better serve our clients. We are evaluating new toolsets, selecting and integrating the best ones for our future-facing IT Service Management platform, EntaraWorks. We are hiring tomorrow’s leaders, giving them the opportunity to grow beyond what they ever imagined.

We’ve been formally recognized as one of Chicago’s Best and Brightest Companies to Work For in both 2017, 2018 and 2019. We’ve made the INC 5000 Top Growing Companies list for the last 3 years! Although we’re ranked among MSPmentor’s Top 200 global IT managed services providers, our customers are generally local to the Chicagoland area. Our sole focus is excellence. If you are fond of the phrase “close enough,” please don’t apply for this job. Our success is built on developing exceptional relationships with fellow co-workers and clients alike, as we collaboratively chart our best paths forward to the future.


You’ll have a direct impact on our operations, our clients, and our fellow EntaraCorps members. Because of that impact, you’ll get our respect and gratitude for the role you play in making Entara the best it can be.

We’ll provide you with skills, training, responsibility and opportunities to grow, both at Entara and wherever your career takes you in the future. (However, we hope you’ll be successful here for a good, long time.)

We know that’s not enough.

Here are some of the perks we currently offer our interns:

  • Competitive, hourly pay
  • Stipends to for discounting housing or commuter costs (when applicable)
  • Inclusion in Company-wide training events, including “Interrogation Sessions”: Entara’s bi-weekly, open forum training session
  • Admittance to our Company-wide outings, be them virtual or in-person. Recent examples of past outings include Ravinia concerts, rooftop barbecues, floating the Chicago River, and vintage gaming, among other things!
  • Social hour with our Leadership Team and discuss career advice & growth
  • Dedicated Career Mentor and Entara Ambassador to follow your journey as an intern with Entara!
  • Schedule time to showcase your work to fellow EntaraCorps, as an end-cap to your summer!

And there’s more…

Our spirit is what makes us different. We work hard. We play hard. We care about each other because we respect where each of us comes from and who we are. We have a more evolved notion of teamwork--solving client problems together and scouring the horizon for new ideas together. We recognize the journey we’re all on, from our clients to ourselves. We’re all at different places on that journey, and each stop requires support, knowledge and courage to move on. It’s why we bring the best tools and support to our clients. And why we treat and reward our EntaraCorps the way we do.