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Breach Remediation: Sr. Systems Engineer

(View all jobs)

Wanted: Resilient Techno-Masters Ready to Remediate!

(also known as a Breach Remediation: Sr. Systems Engineer))


We invite you to collaborate with Entara and further your professional journey with us as a member of our Breach Remediation Project Team. As a top-tier provider of technical service delivery, Entara maintains partnerships that require our team to flex into immediate, high-priority security remediation projects. Project work ranges from remote delivery across varying time zones “dusk to dawn” to jumping on a plane, travelling the continental US to provide onsite support.  These projects are essentially a rescue operation: taking environments in the aftermath of a security breach and restoring them to full operations.

The security remediation work we perform requires extreme care and precision to make sure that we truly cross every t and dot every i, resulting in our client’s ability to get back to work. Engineers will be tasked with an outline of project deliverables, running through a checklist of requirements, and working collectively on issues that arise mid-completion.  This could range from reimaging a server, to restoring backups, to rebuilding or redesigning a VMWare environment.  This team accommodates for more variables than just “getting the lights on”—we also are tasked with improving an environment’s resiliency to attacks and execute projects related to deploying leading security toolsets to our Breach clients. We are a leading Guardicore partner and are actively increasing projects and partnerships to do expand our reach. The work this team performs is dynamic, fast-paced, and requires the self-discipline to “execute the plan” within an aggressive timeline.  Are you ready to roll up your sleeves and jump into the fire with us?  


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

  • Maintain personal Billable Utilization Target as a dedicated BR Sr. Engineer.
  • Plan Recovery Effort.
  • Create Recovery Process.
  • Evolve Technically.
  • Follow Core Process and client communication procedures.
  • Enter Time DAILY before 7PM CST.
  • Mentor Others.
  • Identify Sales Opportunities and follow BR process for specific client, ensure details are captured for sales process.


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

Our BR Sr. Systems Engineers are primarily tasked with providing escalated remote support and project delivery to Entara’s Breach clients. Issues range from backups, workstation, active directory, network, and hypervisor restoration. Project tasks could involve a mix of restoration, re-design, and even security toolset deployment to get Breach clients back to an operational state, whilst shoring up known security vulnerabilities. Our BR Sr. Systems Engineers work as part of a dynamic, flexing team – ready to respond at a moment’s notice. This position reports directly to our Director of Professional Services.

Perform Project Tasks

  • Collaborate on project planning, project design, preparation of deliverables, timelining, and contingency planning.
  • Perform advanced systems configuration, management, and maintenance in areas including the following (as a sample but not an exhaustive listing):
    • Microsoft-related technologies: Windows Server, Exchange, SQL Server, SharePoint, Active Directory, GPO, LAPS, SCCM, MDT, etc.
    • Virtualization technologies: VMware and Microsoft Hyper V
    • Backup and disaster recovery solutions for both desktops and servers
    • Remote access solutions: VPN, Remote Desktop, Citrix, etc.
  • Leverage diagnostic tools; review event logs, Syslogs, monitoring data, and memory dumps to troubleshoot issues.
  • Restore and reimage virtual servers from images and various backup solutions
  • Restore and rebuild ESX and Hyper-V hosts, domain controller, etc.
  • Employ a solid understanding of networking concepts and troubleshooting
  • Deploy and configure security-enhancing solutions for systems and applications (including MFA and endpoint protection).

Meet Measurables

  • Maintain billable utilization targets
  • Record complete change details, time worked entries, and work notes in ServiceNow platform on a real-time basis
  • Contribute to the team’s attainment of high customer satisfaction scores on project delivery

Follow Process:

  • Follow Entara’s project process to execute project deliverables: configure, test, implement, refine, document, monitor, and transition to appropriate stakeholders.
  • Follow Entara’s Change Management Process to perform approved changes in client environments
  • Communicate internally and (as directed) externally to provide timely information regarding project status, promised follow-ups, and requested feedback on a detailed and professional basis. 

Escalation & Troubleshooting

  • Receive escalated systems issues from more junior engineering resources work to resolution
  • Own the issue through completion; determine root cause, locate a clear path to resolution


  • You have at least 5 years of experience delivering IT projects or support working with systems and virtualization, ideally with exposure to enterprise infrastructures. You have at least a four-year degree in a relevant field, and you’ve earned vendor-level certifications such as Microsoft MCSE, VMWare, and VCP. Network-related certifications such as Cisco CCNA/CCNP are a big plus.


  • You’re the ultimate gladiator of the IT environment. Not only do you have a stellar foundation in hardware and operating systems and their diagnostic tools, you can dive deep into the intricate maneuvers within core systems and virtualization technologies and the platforms they’re found on. You are the IT version of Chuck Norris, restoring order to occasionally chaotic systems and ensuring that environments are positioned to run as they should—quietly and problem-free.


  • You have highly developed knowledge of standard employee productivity suites, mobile device configurations and support, switching, network firewalls, and wireless security technologies. You have outstanding operational understanding and previous management of Windows OS (including Window 10 and Window Servers), failover clustering, VMware or Hyper-V, and server hardware. Your knowledge of Active Directory, Windows/Linux, and Storage Area Networks is superb. Microsoft applications such as Exchange, O365, SSCM, MDT, and SQL server are your old friends.


  • You have at least 1 year of experience administering and/or implementing systems in cloud infrastructure such as Azure or AWS. You understand the importance of security as it relates to all applications and systems in an environment. You’ve got a specialty (or several) within systems management but are forever anxious to add new competencies. As a systems pro who refuses to be boxed-in, you’re just as likely to valiantly conquer storage networking and other technologies such as NetApp, Dynamic VPN & IPsec tunnels, and the Cisco device ecosystem. The key to excellence—not to mention a fulfilling life—is continual learning. Entara supports and rewards professional growth.


  • You have an approach to working hours that is more adaptable than the traditional "9-to-5". As this team responds to immediate, business critical remediation projects, we are looking for an individual who is career driven and doesn’t shrink back when work requirements can regularly extend into evenings, weekends, and holidays (50-60 hour weeks are normal). On the flip side, you are motivated to work hard because you are rewarded with a generous comp plan that grows with the efforts you contribute, a flexible PTO policy, and an equally inspiring team who climbs that mountain together.


  • You are ready to be an effective remote worker and have a dedicated, private space for a home office with a capable personal computer and private internet connection with at least 25MBPS bandwidth. Public WiFi and shared common spaces do not meet these standards.


  • 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. 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.


  • The Resilience to Flex: You have seasoned previous storms and developed the flexibility to dive into the deep end at a moment’s notice and “pick up the pieces”. You live for a new opportunity to shine and approach each new challenge without batting an eye.


  • 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.


  • Authoritative, but not autocratic: When tricky issues present themselves, you quickly know which resources to tap to develop solutions—and you understand the nuances of different approaches. You’ll be damned if you’re going to be stumped by a problem you know you can tackle; you consider yourself the consummate troubleshooter. Yet, you lead and delegate to others with clarity, and recognize when it’s time to consult a co-worker for help.


  • Ambidexterity: You extend your hand down to support 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 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 advancing as a leader in the integration between IT and security operations and provide front-line support to businesses recovering from a security breach.  We are hiring tomorrow’s leaders, giving them the opportunity to grow beyond what they ever imagined and to help us re-envision the provider of the future

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. 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.


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
  • Remote working options
  • 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 EntaraNews 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 services, and help to lead our clients and ourselves deep into the future, and Entara becomes 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.