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Systems Engineer I-II (Night Shift)

(View all jobs)

Wanted: A Midnight Manipulator of Cosmic Conundrums

 (Also known as Managed Services: Systems Engineer I-II: Night Shift)


We invite you to join Entara and continue your technical trajectory with us as a Managed Services System 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 infrastructures they fine-tune enable us to deliver superb results at lightning speed.

Our Night-shift Engineers will be tasked with being the primary resolution resource for after-hours support, changes, and maintenance. Whilst preventing fires through proactive monitoring and management of multiple client infrastructures, they never shy away from employing creative troubleshooting when the flames are blazing. They are champions of infrastructure, wrangling client environments into tip-top shape, and juggling service requests and high-priority problems with a professional flair. Our ideal candidate takes immense pride and ownership in everything from the smallest change to strategically reviewing repeated issues and implementing improvement measures. Being a primarily solo role, they have a specific rhythm that keeps them on task and in charge of all the processes simultaneously executing in the wee hours of the morning. Simply put, this role is vital to our success and not just any night owl will do.

Are you the fire-fighting technical connoisseur we’ve been looking for?


(Otherwise known as your “accountabilities”—the most important aspects of your role at Entara.)

  • Primarily focused on client and infrastructure hardware and software such as desktops, laptops, servers, storage, Windows & Linux OS, Active Directory, Group Policy, Exchange, Office 365, Hyper-V, and VMWare.
  • Develop as an SME for specific areas of systems infrastructure and/or specific vendor hardware/software.
  • Address and resolve/close assigned Incidents and Requests.
  • Identify trends and recurring issues, perform root cause analysis, and propose adjustments for increased system stability.
  • Perform after-hours maintenance tasks (i.e. patching, firmware upgrades, application maintenance, audits) and approved, change requests on client environments.
  • Consistently create and update IT Glue documentation, KB documents, and checklists.
  • Adhere to SLA requirements and ensure commitments are followed through on as promised.
  • Serve as Lead Engineer resource for Critical P1 incident process.


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

Night Shift Managed Services Engineers are primarily responsible for providing support to Entara’s clients calling in with systems & network support issues, as well as addressing issues generated by our monitoring systems.  A typical evening will revolve around maintenance tasks and after-hours management of incoming issues and alerts, whether they are generated by our monitoring tools or via a user calling into the service desk. Routine tasks involve leveraging diagnostic tools and employing a mastery of desktops & hardware to address client requests, troubleshoot issues through to resolution, deploy approved changes to infrastructures, and maintain necessary documentation standards—ensuring key systems are secure and operating at their peak 24x7x365. While MS Engineers primarily work on the “manage and maintain” aspect of client support, they will also be responsible for uncovering & executing proactive tasks to ensure all IT Systems & Networks are operational and secure.

Understand the Landscape 

  • Understand current client SLAs, parameters and delivery, keeping your eyes open for continuous delivery opportunities
  • Review & reference logical diagrams, familiarize yourself with client specific requirements and processes – be acutely aware of the environments you manage.
  • 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.
  • Follow Entara configuration 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
  • Employ Business awareness: leverage specific knowledge of the customer and how IT relates to their business strategy and goals

Manage to Near-Perfection 

  • Proactive Maintenance of both physical and virtual systems, including but not limited to:
    • Desktop Systems & Applications
    • Servers
    • Storage
    • Networking:
      • Firewalls
      • Switches
      • Network Security hardware & software
    • Cloud Applications
  • Create and complete approved change requests
  • Perform remote systems and software upgrades
  • Create reporting and metric tracking as it relates to client infrastructure and the services we provide.
  • Ensure complete up-to-date and comprehensive documentation of all systems, leveraged applications, and hardware in client environments is available for all engineers to access
  • Perform Root Cause Analysis on repetitive or major systems-related issues, working with our Sr. Problem Manager to employ solutions

Support Technology

  • Work through a daily schedule in ServiceNow that has been established through the dispatch process
  • Answer after-hours phone calls received through the Entara Service Desk line.
  • Provide support and management of desktop systems & applications, servers, storage, networking, and/or cloud applications based on your areas of expertise.
  • Investigate issues and perform advanced systems troubleshooting in the following areas:
    • Microsoft related technologies: Windows Server, Exchange, SQL, SharePoint, etc.
    • Virtualization technologies: VMware and Microsoft Hyper V
    • Disaster recovery solutions for both desktops and servers
    • Remote access solutions: VPN, Remote Desktop and Citrix.
  • Administer hosted and cloud solutions for customers using technologies that meet their requirements
  • Leverage diagnostic tools, reviewing Event Logs, Syslogs, monitoring data, and memory dumps to troubleshoot issues. Perform intermediate network troubleshooting
  • Communicate with customers as required: keep them informed of Incident and Request progress, notify them of impending changes or agreed outages
  • Develop process documentation for Level 1 Support
  • Update ServiceNow time entries, work notes, and expenses in real-time

Evolve & Escalate

  • Respond to transitioned requests, taking ownership of assigned issues
  • Understand when you need to escalate an issue to the next level
  • Call attention to opportunities for improvement
  • Identify and document patterns of escalation


  • You are completely familiar with client-server networking and the alphabet soup of IT—DNS, WINS, DHCP, VPN, Microsoft MCSE, VMWare VCP1, Cisco CCNA/CCNP—because you have at least five years’ of experience working as an outside support person or at least three years as internal support. You do not have one year of experience repeated 20 times. You either have a four-year degree in a relevant field, or you are working toward one. You’ve earned vendor-level certifications.
  • You’re the grease monkey of the IT environment. You know the ins-and-outs of servers, desktop hardware, and operating systems, are familiar with the diagnostic tools for each, and can put those tools to good use. You are the IT version of the Tappit Brothers on NPR’s Car Talk—throw any problem at them and they have the answer, or they’ll find it. You have comprehensive knowledge of standard employee productivity suites (Microsoft office included), mobile device configurations and support, switching, wireless security and client configuration, and network firewall and security technology. Your knowledge of Active Directory, Windows/Linux, and Storage Area Networks is solid.
  • You understand that maintenance tasks are key to smooth operations and you carry them out consistently. You have an advanced handle on hardware and backup software monitoring and consider yourself the consummate trouble-shooter.
  • 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’re also prepared for trouble by being fluent in disaster recovery prevention, recovery procedures, and backup solutions.
  • You’ve got a specialty within systems and networking support, but constantly keep striving for ways to apply that knowledge further. The key to excellence—not to mention a fulfilling life—is continual learning. You consistently seek out opportunities to learn and pack a bigger punch the next time a similar issue rounds the corner.
  • You’re available to work nights and yes, these regularly include weekends—Entara provides live coverage 24x7 just like a hospital does. We are looking for that rare breed that thrives more at midnight than at midday. You’re open to working 12 hour shifts from 7pm- 7am CDT (with an hour for break) in a rotating schedule. You enjoy the ability to focus on your work, while relishing the increased responsibility you hold while maintaining and managing the full breadth of services offered to our clients.
  • 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 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.
  • Self-Directed and Self-Driven: You’d label yourself as a hard charging, self-motivated individual. You don’t need a drill sergeant barking you orders to spur yourself to action. You are constantly on the lookout for issues requiring your attention and aren’t afraid to call in the troops to combat an issue that is bigger than you can handle solo.
  • 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’re more focused on our clients’ success than being the genius who solves each issue. 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 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. 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.

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 the 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:

  • Ability to perform work 100% remotely
  • BCBS Gold-level PPO Medical Insurance, premiums paid 100% by us
  • Generous and flexible Paid Time Off policy
  • 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.