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

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Open Positions

  • Overnight Dispatch (Remote)
    • Entara’s Overnight Dispatchers are tasked with raising the alarm and executing on key escalation processes to ensure we address the highest priority of issues affecting our client’s infrastructures.

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  • IT Systems Engineer (NYC)
    • Wanted: A World-dominating Techno-champion.

      entara's NYC IT Systems Engineer is primarily responsible for providing first- and second-tier on-site support exclusively to one of entara’s key clients.

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  • Sr. Systems Engineer
    • Wanted: A Techno-master of Galactic Abilities.

      Senior Systems Engineers are responsible for specifying and implementing systems and virtualization solutions, ensuring the stability and performance of client computing environments, and providing a third-tier level of support.

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  • Sr. Network Engineer
    • Wanted: A Techno-master of Interstellar Connectivity.

      Senior Network Engineers are responsible for network solution identification & implementation, ensuring the stability and performance of client networks, and they provide a third-tier level of support for escalated incidents and issues.

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  • Business Development Executive
    • Wanted: A Trail-blazing Ambassador for Sales Expeditions.

      Our Business Development Executives are responsible for building & closing new business relationships with key decision makers at mid-sized organizations in Chicago.

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  • Overnight Infrastructure Engineer
    • Wanted: A Midnight Manipulator of Cosmic Conundrums.

      Overnight Infrastructure Engineers are responsible for providing support to clients calling in with IT infrastructure support issues after hours, and addressing issues generated by our monitoring systems.

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  • IT Network Engineer I
    • Wanted: A World-dominating Techno-champion.

      entara's IT Network Engineers are responsible for providing first- and second-tier support to clients with network and systems support issues, as well as addressing issues raised by our monitoring systems.

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  • IT Engineer Resident
    • Wanted: A Techno-ninja with Cosmic Aspirations.

      IT Engineer Residents are responsible for providing first-level support to entara's clients with network and systems support issues, often serving as the first point of contact.

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  • 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.

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Entara LIFE
Growing Today, Tomorrow and Beyond

The Four e's of Entara


It’s the mindset helping us to truly understand a client’s needs, not just today, but for the future; it’s also the driver of our high-performance team collaboration as new ideas lead us into uncharted territory.



Striving to attain the highest standard of service, vision, and delivery, we value excellence among our teams, and we reward it when we see it in action.



A great idea or solution isn’t great until it’s activated, and we don’t let obstacles win. It’s why we place execution over intention.


We are fascinated by the future. While the world around us disrupts and evolves, we must be on the leading edge to keep learning and growing.


Entara’s 4 e’s drive our teamwork, our client relationships, our rewards, and our promotions.  The result is a culture that is drawing top recruits to our door. They recognize something that all of the EntaraCorps knows; when you consistently model the 4 e’s, you earn that special 5th e over time…
you become an elite member of EntaraCorps.



Few companies offer a portfolio of quality benefits and extras like Entara. We value our EntaraCorps, and our benefits back it up. At a time when employer-sponsored medical insurance is diminishing, Entara pays the full premium for each employee’s Blue Cross Blue Shield (BCBS) Gold-Level PPO medical insurance. We also offer a very generous and flexible paid time off policy where anyone at Entara can take the time off they need and deserve. We believe in and foster life-long learning, so we also reimburse employees for certification tests, and we pay for approved training, conferences, seminars, and more, as we focus on helping each employee reach his or her personal best.

Add Dental, Vision, Life, and Disability insurance, combined with an increasingly rare 401k corporate matching program, and you’ve got the gold standard of employee benefits.

Plus, there are always free snacks and drinks, Monday lunches, and “Fridays at Four.” Combine that with the chance to work at 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 managed services company that’s hard to beat to grow your career today, tomorrow, and beyond.

Benefits at a glance:

  • BCBS Gold-Level PPO Medical Insurance
  • Unlimited PTO
  • 401k Matching Program
  • Reimbursement for approved certification tests & training
  • Life Insurance
  • Dental Insurance
  • Disability Insurance
  • Healthcare Savings Account (HSA)
  • Dependent Care FSA
  • Commuter Benefit Plans

And more…

Free Lunch Mondays, free snacks and drinks, events, awards, team building, and best of all… great colleagues who will likely become great friends!