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Systems Engineer I-II (Managed Services)

Chicago, IL
  • Expired: over a month ago. Applications are no longer accepted.
Job Description
Wanted: A World-dominating Techno-champion of Pivotal Systems(commonly called a Managed Services: Systems Engineer I-II)EMBARK ON YOUR JOURNEY

We invite you to join Entara and continue your system-centric trajectory with us as a Managed Services 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 Systems Engineers will be tasked with preventing fires through proactive monitoring and management of multiple client infrastructures, but they never shy away from employing creative troubleshooting when the flames are blazing. They are champions of infrastructure (where virtual or physical), 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 user request to strategically reviewing repeated issues and implementing improvement measures. Are you the fire-fighting systems connoisseur we've been looking for?


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

Managed Services Systems Engineers are primarily responsible for providing second-tier support to Entara's clients calling in with systems support issues, as well as addressing issues generated by our monitoring systems. 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 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

On-board & Adjust for Additions

  • Perform managed services assigned tasks in relation to implementing new clients, preparing their environments for support
  • Implement additions and changes to customer environments
  • Follow established procedures to capture required information, update documentation, and monitor/manage device and/or individual user

Manage to Near-Perfection

  • Proactive Maintenance of both physical and virtual systems, including but not limited to:
    • Desktop Systems & Applications
    • Servers
    • Storage
    • Networking
    • 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

  • Improve customer service, perception, and satisfaction as a Primary Engineer for your assigned clients.
  • Work through a daily schedule in ServiceNow that has been established through the dispatch process
  • Assist with the 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 basic networks 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

Mindfully Mentor

  • Mentor junior-level engineers, helping them to advance their technical aptitude and application
  • Lend a helping hand and assist junior engineers when needed

Evolve & Escalate

  • Respond to escalation requests from lower-tier teams, 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 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 administration & management).
  • More specifically, you have at least 1-2 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 Powershell and Python. 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 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 may be required to work weekends on rotation or take part in our on-call rotation, it's dependent on your skills and our organizational needs. You are available for a flexing, 9 hour shift generally performed between the hours of 7am-7pm CDT 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 50MBPS 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 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 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.
  • 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, 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.

Founded in 2001, Entara is an eXtended Service Provider (XSP) focused on providing cutting edge technology and cyber security solutions to companies in regulated industries. With our roots in providing service to the electronic trading market, we are known for growing with the pace of technological change and the developing security needs of our clients. We are redefining ourselves - and our industry - and creating a new class of service providers, XSPs, because we recognize that MSPs and MSSPs are no longer what our clients need. Downward pressure from both regulators and insurance providers convinced us that it was time to integrate our IT and cyber security offerings and deliver strategic, future facing solutions for our clients.

In order to build, maintain, and optimize these types of solutions, we need high-performing, highly-collaborative teammates who are excited to join in this journey with us. There are several reasons why employees love being a part of the Entara team. We've been recognized as one of Chicago's Best and Brightest Companies to Work For since 2017. We are a remote-first workplace. We seek to build a team that's brought together by more than just skills, but who embrace a personal-alignment to the values that precede the work we deliver: Empathy, Excellence, Execution, and Evolution. If this sounds like you, let's connect and discover if we have the foundation to build something great together.


As an employee at Entara, you will have a direct impact on our operations, our clients, and your fellow EntaraCorps members. Because of that impact, you get our respect and gratitude for the role you play in making Entara the best it can be. We consider mentoring and participating in the continual learning of others to be absolutely essential for both you and your co-workers.

To reflect our commitment to our employees, we offer unlimited PTO, remote-first work, 401k matching, paid parental leave, employee outings (virtual and in person), reimbursement for approved seminars, conferences, and certifications, and 100% employee premium coverage for medical, dental, life, and disability insurance….and that's just the tip of the iceberg.



Chicago, IL