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IT Executive Systems Engineer (Onsite)

| Greater NYC Area
Apply with a resume and cover letter to the IT Systems Engineer (Onsite) position at: https://grnh.se/7c6a0fc91.
Apply now

Wanted: A World-dominating Techno-champion

(commonly called an IT Executive Systems Engineer)


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

Our NYC IT Executive Systems Engineer is primarily responsible for providing first- and second-tier on-site support exclusively to one of Entara’s key clients. Issues range from desktop support issues for executives to network and systems support issues, as well as working alongside the client team as an integral project resource. Being a role that is relied upon by both our client’s end users and IT staff, this role is integral to the success of one of our key client relationships and is tasked with being the proactive, gap-filler guru versus a master at just “keeping things afloat”. Our NYC Engineer will be the acting face for our company, building our brand in the Big Apple and must be up to the challenge! 

Juggle Operations

  • Acknowledge, prioritize, and troubleshoot tickets assigned to you from the Entara Service Desk and directly from your dedicated client end-users.
  • Assist users at desk-side as required
  • Field onsite inquiries from client IT personnel, determine next steps and scope/priority of issue to ensure successful and timely completion
  • Communicate progress on problems, as well as resolution
  • Exceed SLA guarantees
  • Document all tasks in ITSM platform
  • Become “one” with the client team- you’re their go-to resource and someone they can rely on at the drop of a hat


  • 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 
  • Scout for opportunities to be of more assistance and leverage your skills to identify trending issues to improve existing problems


  • Assist Chicago-based engineers when needed to fulfill on-site client requirements for NYC cliental


  • Respond to escalation requests from lower-tier teams
  • Understand when you need to escalate an issue to the next level
  • Identify and document patterns of escalation 

Employ Technology

  • Complete new computer setups
  • Fix virus/malware issues
  • Configure network printers
  • Resolve computer application and operating system issues
  • Install, configure, and troubleshoot
  • Verify and troubleshoot network connectivity, both wired and wireless
  • Provide mobile device support, including Apple, Android, and Windows devices
  • Manage end-user email experience
    • Master Exchange and Office365
    • Troubleshoot bounce-backs, SPAM, and transmission issues
    • Configure webmail
  • Manage user profiles
  • Navigate Active Directory and Exchange to perform password resets, move/add/change requests, file permission adjustments, and distribution list creation.
  • Troubleshoot and configure basic backups; perform simple file restores
  • Maintain network and systems devices
    • Manage configuration & patching
    • Identify potential configuration improvements
    • Basic Management and Maintenance of Server Applications
      • Active Directory
      • Exchange / Office 365
      • Backup Software
      • SQL Server
      • Antivirus Software


  • You have a minimum of three years’ experience as an outside support resource, or four years working as internal support. You do not have one year of experience repeated 20 times. You have a Bachelor’s degree and a stellar GPA to boot! Your continued focus on growth has lead you to beef up your tool-belt with vendor-level certifications- CCNA and MCSA certifications are a plus!
  • 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 aren’t above doing the “dirty work” of hands on and desk-side troubleshooting. You enjoy putting yourself in the user’s shoes: piecing together an issue- identifying creative solutions-and managing intricate relationships is what you were born to do.
  • You are familiar with client-server networking and the alphabet soup of IT—DNS, WINS, DHCP, VPN, Microsoft MCSE, VMWare VCP1, Cisco CCNA.
  • You’re capable of monitoring and trouble-shooting backup software, reviewing hardware monitoring tools, and trouble-shooting the fundamentals.
  • 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’ve got a specialty, or you want to develop one, within systems and networking support. The key to excellence—not to mention a fulfilling life—is continual learning. Entara supports and rewards professional growth.
  • You are open and available to a schedule that will occasionally fall beyond the constraints of the 8am-5pm Monday-Friday workday. You can make yourself available for after-hours and weekend work as is needed to address the needs of the client, their scheduled changes, and key projects. 

If your skill set 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, please look at our other job openings. One of them may be more suitable, while positioning you to move into a more senior engineer role.


  • Right Brain, Left Brain OS:You’re a little obsessive-compulsive 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 follow 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.
  • Bilingual in English and Tech-speak.You understand what the problem is, even when the person calling is not making sense, 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.
  • 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 or ask for help. Next time, you’ll have the solution at hand.
  • Ambidexterity:You extend your hand to support Engineering Residents, as well as reach up 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.

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.

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
  • 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
  • Travel Reimbursement to join in on Entara outings every quarter and annual trainings!

And there’s 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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Apply with a resume and cover letter to the IT Systems Engineer (Onsite) position at: https://grnh.se/7c6a0fc91.
Apply now
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Apply with a resume and cover letter to the IT Systems Engineer (Onsite) position at: https://grnh.se/7c6a0fc91.
Apply now
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