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Headquarters: 190 S. LaSalle St., Suite 3800 | Chicago, IL 60603-3432

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Sr. Security Engineer (Remote)

(View all jobs)

Wanted: An Anchor of Security Engineering

(also known as a Sr. Security Engineer)


We invite you to join Entara and further your career journey with us as our Sr. Security Engineer. As one of the technical leads for our security practice, this role is not for the faint of heart. We are looking for that rare breed of individual who can both build new ways to deliver services and help us continue to cultivate and mature those approaches going forward. This is not the typical security position where you’re sitting at a desk and tuning SIEMs all day while overflow alerts are coming into the SOC. Our Sr. Security Engineer has a history they can boast about—think DevOps extraordinaire married with a specialization in cybersecurity—you know just how to create and integrate tools to find, prevent, and possibility eliminate malicious activity. You’re known for employing your scripted genius to design solutions for the ever-changing security challenges of today, and you are itching for an opportunity to make another splash in the landscape of security solutions.

Working directly with our Chief Information Security Officer, our Sr. Security Engineer will utilize Entara’s invested security tool-stack to collaborate on a powerful engine of change in the security marketplace. They will be on the forefront of refining the processes and capabilities leveraged by our security practice areas 

While the rest of the world is focused on selling (and reselling) security products, we are focused on bringing meaningful change to organizations’ security. We obsess about a comprehensive approach to cybersecurity that can produce a cycle of resilience for the client. Driving that level of attention and excellence requires a pioneering Sr. Security Engineer to foster continuous development—does that happen to be you?


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

Entara’s Sr. Security Engineer is responsible for developing and integrating Entara’s security stack to meet the needs of our solution-driven services for clients. Our Sr. Security Engineer will act as an SME for all things cybersecurity, covering a wide range of issues from infrastructure design and application development, to researching emerging security challenges and proactively proposing solutions to specific technical problems.

This multi-hat position will report to and primarily interact with our Chief Information Security Officer. The Sr. Security Engineer will spend time building foundational components of our security offerings, and then maintaining and enhancing those components over time. In addition, our Sr. Security Engineer will be relied upon to guide, mentor, and train incoming team-members as a central contributor to this practice, with opportunities to grow into team leadership.

Own Technical Delivery of Security Architecture

  • In alignment with the CISO, weave interactions between disparate security systems into one cohesive unit to support our security services and to improve existing processes.
    • i.e. Update new Python integration to take advantage of a new API feature published by a security vendor.
    • i.e. Use Postman to define complex requests to REST APIs
    • i.e. Work with AWS STS to dynamically provision credentials and resources within S3
  • Work within weekly sprints to deliver requested and required integrations
  • Propose new features or capabilities for inclusion and integration in our product delivery
  • Develop new detection techniques for malicious attackers
  • Keep a finger on the pulse for new security threats, and possibly, solutions within our security services stack.
  • Build new custom playbooks for newly onboarded security service customers
  • Consult and provide guidance on major security incidents
  • Maintain existing security toolsets by continuously iterating and improving

Collaborate & Cultivate Team Relations

  • Establish trust and rapport with team members, creating an atmosphere of shared responsibility and enthusiastic vision-casting
  • Support the Security Analyst team by improving their detection and remediation capabilities
  • Guide, mentor, and train new recruits
  • Delegate and elevate your own position by raising up security professionals to take on routine tasks, keeping yourself as the forefront of key developmental work required to advance our service positioning in the marketplace


  • You have least 3-5 years’ experience gained within a cybersecurity company. Having cut your teeth in a true blue/red team space, penetration testing and application security roles are baked into your work history. You are ready to employ that knowledge into a service-provider setting and put your own stamp on the security marketplace.
  • You consider yourself deeply analytical and your super-power is your programming mastery. You boast extensive development experience within Python and you’ve previously developed integrations with Security Orchestration, Automation, and Response solutions. You also have experience working with APIs (REST APIs and Python).
  • Your experience with scripting languages like Powershell, Perl, Go, etc. runs strong.
  • You have hands on experience with AWS services such as S3, IAM, STS, and Lambda.
  • Our ideal candidate also has knowledge of software engineering releases and experience with CI/CD processes.
  • You are open to a 45-55 hour work week—for you, it’s about your personal follow through, regardless of the time or steps it takes to get there. Quality work takes quality time and it’s not about putting in your hours. You’ll make yourself available to respond to a business-critical fire—you’re committed to the team and committed to building something.
  • 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 Wi-Fi and shared common spaces do not meet these standards. Entara will supply you with other necessary tools and hardware to complete your tasks remotely.


  • Creatively disciplined: You are religious in your approach towards a solution and start on the road well-travelled as a foundation. You’ve also got a streak of Potter’ish ingenuity when something unexpected comes along. You’re not phased when new obstacles block your path and you’re well versed in juggling multiple accountabilities. You break problems down into programmable actions and pay attention to intuitive inspiration—leading to an inventive, yet grounded solution—all without missing a beat.
  • Driven to win: Your sights are set on Olympic gold…all day, every 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. You continually look to fill gaps in security solutions and find ways to improve those that already exist.
  • A Trendsetter: You aren’t phased by being the lone ranger—you’ve been longing for a chance to take the knowledge you’ve gained and reinvent it for a new space. When asked to build something, you run at the end-goal headfirst, paving the way for others to support the foundations you’ve laid. You consider yourself to be an entrepreneur of security solutions and are ready to take a leap into un-charter territory.
  • 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. Your sights are continuously set on “leveling up”, so you enjoy working in an organization that promotes from within. You take a proactive approach towards keeping a pulse on security trends and potential threats that lurk on the horizon, so that you can always be counted on to bring futuristic practices to life.
  • Ambidexterity: You extend your hand down to support security analysts and junior security engineers, as well as reach across the company 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 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 technology 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’re now expanding our security practice to marry products and proactive services. This is a different and cohesive approach to delivering meaningful cybersecurity solutions to companies; we are going beyond the incident, to improve our clients’ security posture using informed offensive tactics.

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 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
  • 100% Remote Working Options
  • 401k Corporate Matching Program
  • Reimbursement for approved certification tests and training, seminars, summits, 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 bi-weekly 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.