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

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Technical Field Engineer

(View all jobs)

Wanted: A Techno-ninja with Face-to-Face Dexterity

(Also known as a Managed Services: Technical Field Engineer)


We invite you to join Entara and start your journey with us as our Technical Field Engineer.

Our Technical Field Engineer plugs 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.

Our Technical Field Engineer provides a unique “boots on the ground” presence for our Chicago-land based clientele. We’re looking for an IT professional who is ready to rock on-site, providing top-tier, desk-side assistance for clients who require a hands-on touch. On days when you’re not scheduled onsite with a client, you’ll report to our Chicago loop headquarters and take the lead on workstation and build tasks, inventory, shipping, and managing, refining, and building images for ease of duplication and scalability.

We are looking for an IT professional who has built up the self-discipline, communication, and problem-solving strengths to be successful in this mixed desktop and client-facing position. Are you the type of people-facing, techo-ninja we’ve been searching for?


(Otherwise known as your "accountabilities" --the most important aspects of your role at Entara.) 

  • Provide exemplary onsite support: attend to client onsite needs as scheduled.
  • Perform Workstation Builds.
  • Manage Image Resources: Image computers, maintain, manage, and build images.
  • Ship equipment out of Chicago headquarters.
  • Follow through Incidents and Requests to resolution.
  • Make and keep client follow up promises.
  • Enter all ticket details in SN for ease of review by all.
  • Communicate clearly with clients and Entara internal teams.
  • Follow KBs, checklists, standards and Incident and Request management processes.
  • Proactively develop technical skills.



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

Our Technical Field Engineer is primarily responsible for providing onsite first- and second-tier support to fulfill pre-scheduled and ad-hoc, onsite requirements with Chicago-land based clientele. Onsite work will range from desktop & mobile support issues for executives to network and systems support issues, as well as working alongside the client team as an integral project resource. This position will additionally work from our Chicago-loop headquarters and will take the lead on workstation builds, related equipment shipping, and ownership of Entara’s and client’s imaging resources. This position will directly report to our Service Delivery Manager.

  • 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 Builds & Imaging Resources
    • Execute workstation and build tasks for Entara and Entara’s clients following established standards.
    • Ship completed builds, coordinate with recipient parties and Entara procurement when needed.
    • Own imaging resources and complete imaging tasks: image computers, manage available images, build new images.
    • Perform 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, as required for user onboardings and workstation builds
  • Support Technology & Users
    • Improve customer service, perception, and satisfaction as an onsite Engineer for recurring weekly onsite assignments.
    • Become a trusted resource to onsite users, assisting desk-side.
    • Work through a daily schedule in ServiceNow that has been established through the dispatch process.
    • Field onsite inquiries from client personnel, determine next steps and scope/priority of issue to ensure successful and timely completion. Create and document all tickets in ServiceNow.
    • Maintain/update server room/environment pictures when onsite.
    • Perform basic Wi-Fi surveys to spot potential issues with coverage or performance.
    • 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.
      • Complete new computer setups: image and deploy
      • Configure and troubleshoot network printers
      • Use and troubleshoot video-conferencing solutions
      • 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
    • Follow established procedures to capture required information and update documentation
    • 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:
    • Entry-level knowledge of Active Directory, with the ability to perform basic user-account administration tasks.
    • A basic understanding of setting up equipment in a server rack, including cable management best practices.
    • Entry-level understanding of office network setups (wired / wireless) and equipment required for best practices network performance
  • You have not only imaged computers, but you’ve mastered the ability to create and build new images to help you scale your individual efforts.
  • You are physically capable of lifting up to 40 pounds of equipment in the course of a standard workday, carrying hardware and workstations up or down flights of stairs to their designated locations.
  • You know that maintenance tasks, consistently carried out, are essential to smooth server operations.
  • 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.

  • On a regular day, you’re available to work out of our Chicago-loop office and are additionally available to travel onsite to client locations based in the Chicago loop or the surrounding Chicagoland area (on average up to a 30-mile radius, not to exceed a 50-mile radius), primarily between the hours of 8:00am – 5:00pm CST in a Monday-Friday work week. You have reliable transportation (a personal car is preferable) or access to public transportation in order to travel to and from client locations and Entara’s headquarters.


  • 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 been 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. 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, premiums paid 100% by us
  • Disability Insurance, premiums paid 100% by us
  • Life Insurance, premiums paid 100% by us with option for buy-up for additional coverage
  • Healthcare Savings Account (HSA)
  • Dependent Care FSA
  • Granted it’s safe to do so, Company-wide outings every six months and virtual events sprinkled in-between! Historic examples include outdoor 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 a weekly internal News show. 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.