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Breach Remediation: Contract Network Engineer

(View all jobs)

Wanted: Flexible, Voyaging Techno-Masters Ready to Remediate!

(also known as a Breach Remediation: Contract Network 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 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 VPN configurations to installing firewalls to re-designing and deploying a network.  The work 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?  



Given our aggressive growth and varying project sprints, we are seeking immediately available network engineers who are interested in exploring their fit with Entara and who would be open to a contract position as a primary point of entry into our organization.

We are seeking contractors who are comfortable committing to being a member of our active, contractor bench. Being on the bench does not mean that you are guaranteed full-time work or consistent hours. Rather, bench contractors are considered flexible resources that are vetted and assigned as project sprints arise for completion.

Project sprints could last as little as a few days up to full-time hours for a month (sometimes more). The assigned project hours are based both on the contractor’s flexibility and the needs of Entara at the time of outreach. It is the assumption that contractors will seek to maintain somewhat consistent availability in hours and the openness to travel in order to be prioritized for future outreach and assignment of hours.

In essence, we are seeking to establish relationships that allow flexibility for both the contractor and for Entara.

If you’re open to this type of arrangement, keep on reading!



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

Our Contracted Network Engineers are primarily tasked with providing escalated remote and onsite support to Entara’s Breach clients. Issues center around network design, configuration, and implementation to re-establish connections with a focus on enhanced security measures.

  • Assigned project work could encompass any of the following tasks & requirements:
    • Work through a daily schedule in ServiceNow that has been established through the project management process. Be available to acknowledge your assigned tasks.
    • Provide insight on project planning, project design, preparation of deliverables, timelining, and contingency planning.
    • Perform intermediate-advanced network configuration, management, and maintenance in areas including the following (a sample, but not an exhaustive listing):
      • Firewall installation, design, & configuration: Palo Alto, Cisco Firepower, Meraki
      • Fine-tune next gen firewall features: content filtering, geo blocking, IDS/IPS, SSL Decrypt
      • Perform site to site VPN configuration and troubleshooting
      • Perform client VPN configuration and troubleshooting
      • Design and troubleshoot static and dynamic routing (WAN/LAN)
      • Virtualization networking design, configuration, and troubleshooting:
        • VMware | Hyper V
        • Cloud: Azure | AWS
      • Out of band network design and configuration
    • Communicate with Project Managers as required: actively keep them informed of restoration progress and escalation requirements, notify them of impending changes or agreed outages.
    • Update ServiceNow time entries, change details, work notes, and expenses in real-time.
    • Receive escalated networking issues from more junior engineering resources, or overflow from other engineering groups and work to resolution.



  • You are completely familiar with client-server networking and the alphabet soup of IT—DNS, WINS, DHCP, VPN, Cisco CCNP—because you have at least 3-5 years’ experience working as a consummate network guru: managing and fine-tuning environments from design to deployment.
  • You have an understanding of concepts like trunking, multi- and single-mode fiber circuits and cross-connects, VLAN tagging, and link aggregation. You’re very familiar with Cisco device ecosystem and can navigate Cisco IOS with ease. You are equally competent working with Juniper, Palo Alto, and Meraki devices.
  • You are familiar with and interested in technologies such as Azure networking, Citrix NetScaler appliances, security appliances such as Palo Alto or other Deep Packet Inspection and SSL decrypt devices. You are also familiar with protocol concepts such as WAN optimization, CoS/QoS, and multicast. You have experience utilizing Microsegmentation in network design.
  • You’re the grease monkey of the IT environment. You have highly developed knowledge and experience with standard employee productivity suites, mobile devices, switching, network firewalls, and wireless security technologies. You 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.
  • Having exposure to the following areas are a definite plus: Virtualization background (VMware, HyperV), server and VM builds and configuration, basic familiarity with application architecture, and Active Directory.
  • You’re open to a flexible schedule, assigned upon project sprints. Hours requested could be as little as a handful of hours worked at night to working 8-10 hours days onsite at a client location. Yes, there will be requests for weekends and late-night hours. You will have the flexibility to say no to any project requests. *Please note that consistent unavailability may mean you aren’t the first in line for placement on our next project sprint.*
  • 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.
  • You are a voyager at heart: prepared and open to travel domestically at short or no notice. Required travel is arranged by the contractor, but costs related to flights, lodging, etc. are invoiced to Entara and reimbursed. Given the Covid-19 pandemic and onsite requirements, trips that extend beyond a single day engagement are afforded an allowance for obtaining PPE (personal protective equipment): masks & sanitizer.  



We seek to align our business with contractors who display the following attributes:

  • A Commitment to Solve: Our most successful contractors have balanced the art of breaking problems down to their core. While using logical processes to find a solution is repeatable, the shining stars are those who can spot a variance a mile off and use their Potter-ish ingenuity when something weird comes along and needs a creative solution.
  • An Eye for Detailed Execution: We value relationships that we don’t have to micro-manage. You take pride in what you sign your name to and are known for your reliability, follow-through, and spot-on deliverables.
  • The Resilience to Flex: The nature of this relationship is one that requires flexibility and the willingness to dive into the deep end at a moment’s notice and “pick up the pieces”. Half of the battle we face is finding those with the resilience to step into a new challenge and environment without batting an eye.
  • A Partner in Success: With any relationship we establish, we desire true partnerships that are mutually beneficial. 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.



Selected individuals will be hired as 1099 contractors and trained on the applicable tools and systems utilized for their assigned projects.

This contract relationships allows streamlined onboarding into our organization and opens the door for interaction within our team that may garner eligibility for subsequent employment opportunities and diverse roles within our various service delivery teams. Contract engineers would be fast-tracked for consideration regarding our full-time, perm positions within Entara, allowing both the engineer and Entara to assess the right role alignment within our organization.

Tasks will be performed in either a remote or hands-on capacity (assigned based on project requirements).



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 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.



You’ll have a direct impact on our clients and the rest of EntaraCorps, helping us to rebuild technical foundations all the while establishing a budding client relationship that in turn grows Entara. Because of that impact, you’ll get our respect and gratitude for the role you play in making Entara the best it can be.

Here are some of the relationship highlights to consider:

  • Competitive, hourly pay based on level and skill alignment.
  • Flexible hours based on your availability: Monday-Sunday work available, day into late night!
  • Opportunities to convert to perm positions with Entara in the areas of Managed Services, Professional Services: Project Delivery, or as a Breach Remediation Project Engineer!
  • Contribute to a team culture that fosters & lives by our core values:
    • Empathy: I put team and client before self.
    • Excellence: I find inner joy in producing excellence.
    • Execution: I value execution over intention in myself & others.
    • Evolution: I am future-fascinated. Improvement is a lifelong quest.



Apply Today! Questions can be directed to Tiffany at