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Overnight Infrastructure Engineer (Remote)

| Chicago

Wanted: A Midnight Manipulator of Cosmic Conundrums

 (Also known as a Remote Overnight Infrastructure Engineer)


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

Overnight Infrastructure Engineers are primarily responsible for taking the lead on providing support to Entara’s clients calling in with IT infrastructure support issues, as well as addressing issues generated by our monitoring systems. Engineers also have the opportunity to assist with client projects via the professional services delivery team. 

  • Employ Technology
    • Perform advanced systems troubleshooting
    • Perform advanced network troubleshooting
    • Maintain network and systems devices
      • Manage configuration & patching
      • Identify potential configuration improvements
      • Manage and maintain server applications:
        • Active Directory
        • Exchange / Office 365
        • Backup Software
        • SQL Server
        • Antivirus Software
      • Administer monitoring and management tools
  • Review
    • Look over current client SLAs, parameters and delivery, keeping your eyes open for continuous delivery opportunities
    • Ensure documentation and current client information is consistently updated
  • Analyze
    • Complete reporting and metric tracking
    • Assess overall health of the infrastructure, making recommendations before issues become service impacting
  • Collaborate and Escalate
    • Drive issues to resolution through effective communication with teammates on day shift: providing thorough details, notes, and context for a smooth transition and effective team troubleshooting
    • Respond to escalation requests
    • Proactively escalate issues to drive results and ensure client uptime

Our clients sleep soundly knowing that Entara is at the helm day and night, 24x7x365. The Overnight Engineers at Entara are on a playing field all their own. They own the night, keeping tabs on every issue or alert that could negatively impact our clients’ workdays and driving them to resolution. They know their own limits, and aren’t afraid to engage the rest of the team in order to ensure uptime. They have an impeccable knack for effectively communicating what needs to be done and looping in the right taskforce to accomplish the seemingly impossible—it’s just all in a night’s work. 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.


  • 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 three years’ of experience working as an outside support person or at least two 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 local, 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 (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.

If your skillset doesn’t meet these requirements, you won’t be a fit for this job. Please don’t apply. If you’re working toward this skill level, we’d love to hear from you down the road as you continue to develop.


  • Right Brain, Left Brain OS: You’re a little obsessive-compulsive 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.

We’re serious about these qualities. If they don’t apply to you, you won’t be happy at Entara and we won’t be happy with you. We’ll part ways sooner rather than later.  Let’s avoid all that discomfort by agreeing you won’t contort yourself to meet requirements that just don’t fit. You are who you are, and that’s okay.


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 in both 2017 and 2018. Although we’re ranked among MSPmentor’s Top 200 global IT managed services providers, our customers are generally local to the Chicagoland area. 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.

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:

  • Ability to perform work 100% remotely: limited to IL and NY residents with a private, home office 
  • 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
  • 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 Headquarters, among other things!

And there’s more…

Free snacks and drinks, weekly lunches, and “Fridays at Four.” 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.

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