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

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IT Engineer Resident

(View all jobs)

Wanted: A Techno-ninja with Cosmic Aspirations

(Also known as a Managed Services: IT Engineer Resident)


We invite you to join Entara and start your journey with us as an IT Engineer Resident. This fast-tracked, multi-faceted position is where many EntaraCorps begin their career progression into further technical (and even some non-technical) positions that influence our clients lives on a daily basis.

Our Engineer Residents plug into our Managed Services team. This team is the lifeblood of our organization and plays an integral role in the daily IT operations for a variety of different business landscapes 24x7x365. They are a team that remediates fires, jumps through technical hoops, and identifies opportunities for advancement. The issues our engineers solve day in and day out, enable our clients to work and operate in tip-top shape, knowing that we have their back when it all goes up in flames.

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 position 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.

This particular residency is based in the Chicagoland area, where the majority of Entara’s clients are headquartered. While you call the Chicago area home, your work life will more regularly consist of working from home than showing up to an office each day (at least until the health climate calms down). We are looking for an IT professional who is ready to hit the phones, work that ticket, and who has built up the self-discipline, communication, and problem-solving strengths to be successful in this mixed work from home and client-facing position.

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.


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

Our IT Engineer Residents are primarily responsible for providing first and second-tier remote and onsite support to Entara’s clients in their assigned region. Issues range from desktop support issues for all levels of end-users to network and systems support issues. IT Engineer Residents tend to be the first point of contact for our client-base and regularly employ the ability to translate technical issues into actionable next steps and gap-filling solutions. IT Engineer Residents work as a part of engineer “pods” that act as a support family for their assigned clients. Within this pod, IT Engineer Residents can escalate and tackle issues—gaining additional exposure and support in a team-centric atmosphere

  • Understand the Landscape
    • Understand current client SLAs, parameters and delivery, keeping your eyes open for opportunities to make an end-user’s life easier.
    • Familiarize yourself with client specific requirements, tools, and processes – be acutely aware of the environments you’re working within.
    • Stay aware of open vendor and client issues. Research historical performance (by user and by client), to ensure the solution we’re applying isn’t just a band-aid solution. Identify and escalate problem tickets to our Sr. Problem Manager to employ solutions.
    • Follow Entara standards to ensure client systems are following best practices.
    • Review IT publications and online materials to remain up-to-date with current and future technologies emerging in the industry.
  • Manage & Adjust
    • Perform managed services assigned tasks in relation to managing user profiles: Navigate Active Directory and Exchange to perform password resets, move/add/change requests, file permission adjustments, and distribution list creation.
    • Follow established procedures to capture required information and update documentation
  • Support Technology & Users
    • Improve customer service, perception, and satisfaction as a dedicated Engineer for your assigned clients.
    • Become a trusted resource to users, assisting desk-side as required.
    • Work through a daily schedule in ServiceNow that has been established through the dispatch process. Be available to “answer the phones” when scheduled.
    • Assist with the support of desktop systems & applications, occasionally diving into servers, databases, networks, and/or cloud-based systems depending on where you’d like to specialize.
    • Investigate issues and perform end-user and systems troubleshooting in the following areas:
      • Microsoft related technologies: Exchange, O365, SharePoint, etc.
      • Managed email experience: troubleshoot bounce-backs, SPAM, and transmission issues. Configure webmail.
      • Remote access solutions: VPN, Remote Desktop and Citrix.
      • Computer new computer setups
      • Configure network printers
      • Fix virus/malware issues, respond to phishing alerts/flags
      • Configure basic backups and perform file restores
      • Perform basic network connectivity troubleshooting, wired and wireless
      • Provide mobile device support, including Apple, Android, and Windows devices
    • Communicate with customers as required: keep them informed of Incident and Request progress, notify them of impending changes or agreed outages
    • Provide input on current processes and documentation for Level 1 Support
    • Update ServiceNow time entries, work notes, and expenses in real-time
  • Evolve & Escalate
    • Take ownership of assigned issues and work as a team
    • Understand when you need to escalate an issue to the next level
    • Call attention to opportunities for improvement
    • Identify patterns of escalation
    • Seek to advance your knowledge and apply learned insight to repeated tasks


  • You have a minimum of two years experience as an outside support resource, or three years working as internal support. You either have a Bachelor’s degree or you’re actively working toward completion of one. CompTIA and Cisco certifications are a definite plus.
  • You’re getting to be the grease monkey of the IT environment. You have a firm 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 fully understand mobile device configurations and support.
  • You have a basic understanding of networking principles, including:
    • Client-server networking, switching, and the Alphabet Soup of TCP/IP—DNS, WINS, DHCP, routing and internet.
    • CAT5/CAT6 wiring, including wireless security and client configuration, and network firewall and security technology.
    • Entry-level knowledge of Active Directory, with the ability to perform basic user-account administration tasks.
  • You know that maintenance tasks, consistently carried out, are essential to smooth server operations.
  • You’re capable of monitoring and trouble-shooting backup software, reviewing hardware monitoring tools, and trouble-shooting the fundamentals.
  • When the baby gets sick, you know what to do. You have corporate anti-virus software experience (preferably Symantec Endpoint Protection), as well as experience removing viruses and spyware.
  • You have an approach to working hours that is more adaptable than the traditional "9-to-5". You're career driven and motivated to put in the time and effort to get the job done right, and you take immense pride in your personal follow-through. At the same time, you can grasp what to prioritize, when to call it a day, and how best to build in some breaks for personal wellness. Balancing work and life well is an art you value in yourself and one that Entara fully supports. You need to be at your best in order to do your best, and that starts with building healthy work habits--something we are continuously pursuing together.

  • You’re available to work later shifts (ending around 7pm CST) and weekends in a rotation, while getting days off. Yes, there will be weekends and changing shifts— Entara provides local, live coverage 24/7 just like a hospital does.  We believe we’ve found the best compromise between delivering round-the-clock service and still creating a learning atmosphere where residents get a taste of everything—day and night—and aren’t “stuck” in a single, static shift. These hours might initially seem like an adjustment, but our residents tell us that they learn a lot during these times that they would never learn in another “regular” job. As any doctor will tell you, the shift work doesn’t last forever.  Once you’ve proven your knowledge, you’ll be promoted to Engineer and be the person training the next class of residents. 
  • You are ready to be an effective remote worker and 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 the other necessary tools and hardware to complete your tasks remotely.


  • 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 calling the Service Desk and are therefore 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. 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.  


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 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 since 2017. We’ve also been named in the INC 5000 Top Growing Companies for the past three years! We’re also ranked among MSPmentor’s Top 200 global IT managed services providers, and our influence has expanded beyond the Chicago arena. 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.

Yes, we’re techies, geeks and nerds. But Entara’s excellence is all about relationships, not technology. We build—and build on—trust with co-workers, end-users, clients and their clients and employees. Entara’s mission is to make those people’s lives easier and their businesses more successful by resolving their IT issues and managing their systems. Bonded to your computer screens? Don’t apply for this position. Interested in building more than internet connections? Come on board.

Frodo couldn’t do it alone. He needed a team. Entara values teamwork and collegiality, especially on those days that feel like a march to Mordor.  At Entara, everyone has a role to play, everyone leads in one situation or another, and everyone has the opportunity to grow into positions of increasing responsibility. If your goal is to be Lord of the Ring, please don’t apply for this job. If you want to join the Fellowship of the Ring, please do apply!


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 consider mentoring and participating in the continual learning of others to be absolutely essential for both you and your co-workers. You’ll benefit by developing your leadership skills—and by having a replacement ready when you’re ready to move up to another position.

We know that’s not enough.

Here are some of the employee benefits we currently offer:

  • BCBS Gold-level PPO Medical Insurance, premiums paid 100% by us
  • Generous and flexible Paid Time Off policy
  • Remote Working Options
  • 401k Corporate Matching Program
  • Reimbursement for approved certification tests and training, seminars, conferences and more
  • Dental Insurance
  • Disability Insurance
  • Life Insurance
  • Healthcare Savings Account (HSA)
  • Dependent Care FSA
  • Tax-advantaged Commuter Benefit Plans
  • Company-wide outings every three months. Recent examples include Ravinia concerts, rooftop barbecues, floating the Chicago River, bowling & bocce, laser tag, and vintage gaming at a local Beercade, among other things!

And there’s more…

Virtual “Fridays at Four” and bi-weekly Wellness coaching sessions. Combine that with the chance to work with a variety of clients in some of the most interesting industries around, solve big problems, create new pathways in managed services, and help to lead our clients and ourselves deep into the future, and Entara becomes the one IT company that’s hard to beat.

And there’s even 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.