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Systems Engineer II (Project Delivery)

(View all jobs)

Wanted: A World-dominating Techno-champion of Pivotal Systems

(commonly called a Project Delivery: Systems Engineer II)



We invite you to join Entara and continue your system-centric trajectory with us as a Project Delivery Systems Engineer! Entara’s Project Delivery team is regularly leveraged as the special forces when it comes to technical alignment and optimization for our clients. They are a team that identifies technical issues and respond with future-minded solutions. They don’t stop after the proof of concept—this same team takes the lead on all significant implementations, changes, and deployments that affect Entara’s client-base. They are the pre-sales technical voice, the project leaders, the change makers, and a point of escalation on the call-tree for raging fires.  The work they deliver evolves our client’s technical landscapes- making them more efficient, effective, and secure than they were previously.

Our Systems Engineers are skilled in the art of leveraging and implementing the latest technical advancements into a variety of environments, often with multiple stakeholders and coinciding deliverables. They are champions of infrastructure (whether virtual or physical), employing and deploying tools and tasks with precision to make the necessary changes that lead to tip-top operations post-project. Our Systems Engineers bring the term “renaissance man (or woman)” to life—they tackle systems and toolsets ranging from a mastery of everything Windows to employing Powershell to get the job done in less time. They are slightly obsessed with the idea of a “perfect” go-live and bring with them a disciplined disposition towards execution even when they have multiple projects in tow. In other words, our Systems Engineers are a powerhouse of through-put and strategic impact. Are you the type of systems champion we’ve been looking for?


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

Project Delivery Systems Engineers are primarily responsible for implementing system solutions for Entara’s clients, and for ensuring the stability and performance of client systems. Systems Engineers also act as additional sticky situation guides and as an escalated resource when the Managed Services Team needs backup. They are focused on elements of project development and design, whilst being focused on delivery. While they primarily work on improvement measures for current clients, they flex into on-boarding tasks, establishing that initial technical rapport with Entara’s newest clientele. Being part of a team that is primarily project based, our Systems Engineers are required to maintain billable utilization thresholds and optimize their time towards client-facing deliverables.

  • Design Solutions
    • Review escalated project suggestions from client account managers to determine most effective solution for proposal based on Entara standards
    • Proactively identify and remedy risks in customer environments
    • Assist in developing strategic & timely solutions in response to client needs and requests
    • Leverage and maintain Entara standards in solution design 
  • Deliver Projects
    • Follow Entara’s project process to execute project deliverables: configure, test, implement, refine, document, monitor, and transition to managed services for ongoing maintenance and support 
    • Work closely with Managed Services engineers on troubleshooting issues or addressing changes that may be needed to ensure systems and tools are operational and functioning as intended
    • Follow Entara’s Change Management Process to perform approved changes in client environments
    • When necessary, participate in Change Advisory Board (CAB) meetings
    • Maintain Billable Utilization
    • Maintain high project CSAT metrics per scorecard
  • Illuminate Relationships
    • Take ownership for client experience:
      • Guarantee project deliverables are met; ensure customers are satisfied
      • Look for ways to improve project experience (internally & externally)
    • Ensure client documentation is complete, accurate, and up-to-date upon transition to Managed Services
    • Interpret technology concepts to clients in a way that is meaningful and valuable to their business
    • Research and recommend new systems, technologies, tools, and platforms
    • Identify process improvements which will increase efficiency or reduce risk
  • Resolve Issues
    • Own the issue through completion: troubleshoot advanced escalated systems issues, determine root cause, and implement solutions
    • Act as an additional point of escalation for Entara systems engineers for hard-to-solve operational issues
    • Participate in systems on-call rotation for Entara clients
    • Update ServiceNow time & project entries, work notes, and expenses in real-time
  • Mentor Mindfully
    • Delegate tasks when appropriate to improve efficiency and offer growth opportunities for other team members
    • Cross-train with other engineers
    • Mentor junior-level engineers, helping them to advance their technical aptitude and application
  • Flex into Operations
    • Remain flexible to changing needs within Entara service delivery teams, employ knowledge and prior experience in operations to provide additional support to Managed Services team in seasons of high or unexpected increases in volume.
    • Sample tasks may include the following:
    • Proactive Maintenance and support of both physical and virtual systems:
      • Desktop Systems & Applications
      • Servers
      • Storage
      • Networking
      • Cloud Applications
    • Create and complete approved change requests
    • 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.
    • Leverage diagnostic tools, reviewing Event Logs, Syslogs, monitoring data, and memory dumps to troubleshoot issues.
    • Perform basic networks troubleshooting
    • Communicate with customers as required: keep them informed of Incident and Request progress, notify them of impending changes or agreed outages
    • Respond to escalation requests from lower-tier teams, taking ownership of assigned issues
    • Update ServiceNow time entries, work notes, and expenses in real-time


  • You are completely familiar with client-server networking and the alphabet soup of IT—DNS, WINS, DHCP, VPN, Microsoft MCSA, VMWare VCP1, Cisco CCNA—because you have at least three years’ of experience working as a consummate support professional (ideally with a heavy focus on systems management and project deployment).
  • More specifically, you have at least 5 years of experience administering Windows Operating Systems (including Windows 10 and Windows Server) and managing DNS, CIFS, Active Directory, Exchange/Office 365, SQL Server. 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.
  • Desktop applications such as Microsoft Office Suite, Remote Desktop, Quickbooks, Adobe Acrobat. Internet Browsers, and VPN clients—you know them like the back of your hand.
  • You are gaining expertise in managing cloud-based infrastructure, specifically leveraging Azure and/or AWS.
  • You additionally have comprehensive knowledge of standard employee productivity suites mobile device configurations, switching, wireless security and client configuration. You have foundational understanding of network route, switch, firewall and security technology (including NAT policies). You’ve been exposed to (and ideally have leveraged) Powershell and Python. Your knowledge of Active Directory, Windows/Linux, and Storage Area Networks is solid.
  • 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 and threat protection software experience, 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 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 (1 week out of every 4-6 weeks) and as a project resource, you will complete tasks that may occur afterhours or on a weekend.
  • 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.
  • While you are primarily a remote worker, you are open to the occasional “on-site” project requirement and are willing and able to jump on a plane if required for implementation.


  • 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 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 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 are operating on their last nerve and seeking a solution to make their lives easier. 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.
  • 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.
  • Ambidexterity: You extend your hand down to support Engineering Residents and fellow Engineers, 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.


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 also been named in the INC 5000 Top Growing Companies for the past three years! We’re also 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 Wellness coaching sessions. 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.