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

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Sr. Systems Engineer (Managed Services)

(View all jobs)

Wanted: A Systems-centric Techno-master of Galactic Abilities

(Also known as a Managed Services: Sr. Systems Engineer)


We invite you to join Entara and wield your mastery of “everything systems” as a Managed Services Sr. Systems Engineer! Entara’s Managed Services 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 changes they implement, the tools they leverage, and the systems they fine-tune enable us to deliver superb results at lightning speed.

Our Sr. Systems Engineers have already fought their fair share of fires and yet—they never shy away from an opportunity to flex their technical muscles and assist the team when the flames are blazing. They come to Entara as subject matter experts in the areas of physical and virtualized infrastructures, the “cloud”, storage, and EVERYTHING Windows. They have regularly employed custom scripts to automate and systematize the environments they manage. Their systems mastery helps them to remediate the day-to-day fires and has lead them to review client environments with an eye for continuous improvement. They are the jedi-masters of their environments, from solving the most complex server issues to walking clients through their technical options for accomplishing X, Y, & Z – our Sr. Systems Engineers are a powerhouse of creative thinking and disciplined execution. Are you the type of systems guru we’ve been looking for?


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

Managed Services Sr. Systems Engineers are primarily responsible for providing escalated support to ensure the stability and performance of client computing environments 24x7x365. Sr. Systems Engineers act as a Senior technical resource and provide a third-tier level of support for incidents and issues escalated from the Service Desk. While Sr. Systems Engineers primarily work on the “respond, manage, and maintain” aspect of client support, their technical expertise is also leveraged to identify problems for resolution and guide and develop their team’s engineers.   

Master the Landscape

  • Understand current client SLAs, parameters and delivery, keeping your eyes open for continuous delivery opportunities
  • Stay abreast of changes performed by vendors and other Entara teams that may affect delivery. Work closely with these teams on remediation should issues arise.
  • Think Ahead: Research and work with platform and technical alignment team members to recommend new systems, technologies, tools, and platforms for Entara or client usage

Champion Operational Support & Escalations

  • Work through a daily ticket queue of escalations in ServiceNow that has been established through the dispatch process
  • Answer escalation questions from other engineers on your team to enable them to solve more complex tickets
  • Provide the other engineers on your team guidance on the escalation process and when to escalate tickets
  • Review technical work completed, KBs written, solutions implemented by other engineers on your team
  • Be familiar with and able to employ foundations of ITIL framework, including identification of problem tickets and parent incidents
  • Assist in identifying out-of-scope tasks
  • Troubleshoot complex systems and application issues, determine and document root cause, and implement solutions
  • Document solutions and draft KB articles for complex incident remediation, assisting engineers to implement solutions you’ve identified.
  • Manage hosted and cloud solutions for customers using technologies that meet their requirements. Develop and deploy solutions to customer systems requests.
  • Proactively identify and remedy risks in customer environments.
  • Follow Major Incident Management process to action P1 incidents and eliminate widespread reactive incidents in client environments as quickly as possible

Strengthen Customer Relationships

  • Improve customer service, perception, and satisfaction as a Senior Engineer for your assigned clients.
  • Take ownership for client experience:
    • Guarantee SLA’s are met; ensure customers are satisfied
  • Look for ways to improve continuous service delivery. Ensure client documentation is complete, accurate, and up-to-date
  • Become a trusted technical advisor for clients by identifying out-of-alignment configurations and systems. Interpret metrics and explain technology concepts to customers in a way that is specific and valuable to their business.

Mindfully Mentor

  • Delegate tasks when appropriate to improve efficiency and offer growth opportunities for other team members
  • Cross-train with other engineers and provide cross-training opportunities
  • Mentor junior engineers, helping them to advance their technical aptitude and application


  • You are completely familiar with the extended alphabet soup of IT—TCP, UDP, DNS, WINS, DHCP, VPN, GPO, VLAN, 10GbE/1GbE—because you have at least four years of experience working with systems and virtualization. You do not have one year of experience repeated 20 times. You have at least a four-year degree in a relevant field, and you’ve earned vendor-level certifications such as Microsoft MCSE, VMWare, and VCP. Network-related certifications such as Cisco CCNA/CCNP are a big plus.
  • You’re the ultimate gladiator of the IT environment. Not only do you have a stellar foundation in hardware and operating systems and their diagnostic tools, but you can dive deep into the intricate maneuvers within core systems and virtualization technologies and the platforms they’re found on. You are the IT version of Chuck Norris, restoring order to occasionally chaotic systems and ensuring that environments are positioned to run as they should—quietly and problem-free.
  • You have highly developed knowledge of standard employee productivity suites, mobile device configurations and support, switching, network firewalls, and wireless security technologies. You have outstanding operational understanding of Windows OS/servers, failover clustering, VMware concepts, and server hardware. Your knowledge of Active Directory, Windows/Linux, and Storage Area Networks is superb. Microsoft applications such as Exchange, O365, and SQL server are your old friends.
  • You have at least 1 year of experience administering and/or implementing systems in cloud infrastructure, primarily in Azure or AWS. You understand the importance of security as it relates to all applications and systems in an environment.
  • You have a knack for wielding PowerShell or Python scripting to tackle complex systems issues.
  • You’ve got a specialty (or several) within systems support but are forever anxious to add new competencies. As a systems pro who refuses to be boxed-in, you’re just as likely to valiantly conquer storage networking and other technologies such as NetApp, Dynamic VPN & IPsec tunnels, and the Cisco device ecosystem.
  • 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.
  • As a Systems Engineer, you will be a dedicated member of our on-call rotation, covering 1 week out of every 6 weeks. You are available for a flexing, 9 hour shift generally performed between the hours of 7am-7pm CST Monday-Friday.
  • 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 knowledge of documented issues and 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 develop complex, detailed instructions for complex, detailed tasks. Again, you avoid even thinking, “That’s good enough.” As someone who respects others’ time and manages expectations, you consider being “on-time” a virtue and see following through on commitments as the Holy Grail of your personal work ethic. You continually look to fill gaps in process, and find ways to improve those that already exist.
  • Bilingual in English and Tech-speak. You understand what the problem is, even when the person calling is in-decipherable, 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. You enjoy sharing knowledge, working towards a solution, and do so in a way that’s respectful and understanding.
  • 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.
  • Authoritative, but not autocratic: When tricky issues present themselves, you quickly know which resources to tap to develop solutions—and you understand the nuances of different approaches. You’ll be damned if you’re going to be stumped by a problem you know you can tackle; you consider yourself the consummate troubleshooter. Yet, you lead and delegate to others with clarity, and recognize when it’s time to consult a co-worker for help.
  • Ambidexterity: You extend your hand down to support more junior engineers, as well as reach across the company for help when you need it. You’re adept at balancing your own workload with the responsibilities of the team. You’re intentional about sharing constructive feedback and ideas with colleagues while welcoming the same in return.


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 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. 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, 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 security services, and help to lead our clients and ourselves deep into the future, and Entara becomes one 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 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.