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This position has closed. Wintrust removed this listing from their careers page on Sep 25, 2026. The interview prep below is still useful, and there are similar open roles at the bottom of this page.

Senior Network Security Engineer

Wintrust · Chicago, IL · $117,000–$158,000 a year · Full time

Posted Sep 18, 2026 · We last checked this listing on Sep 22, 2026

Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

What would you do

Your automation is about to push a change that would cut connectivity. How do you catch that first?

What they are checking: The risk that makes network automation frightening, and testing is the answer.

About the work

Tell me about automating network security configuration.

What they are checking: The posting is explicitly a network security automation role.

What is configuration drift, and how would you detect it?

What they are checking: The posting names automated compliance and configuration-drift monitoring against approved architecture.

How would you find an overly permissive firewall rule at scale?

What they are checking: The posting names access-rule analysis and identifying overly permissive or unauthorized network paths.

Walk me through automating a firewall policy deployment safely.

What they are checking: The posting names firewall-policy deployment automation.

How do you build rollback into a network change pipeline?

What they are checking: The posting names approval gates, version control and rollback capabilities in CI/CD.

Tell me about something you have written in Python or PowerShell for network work.

What they are checking: The posting requires strong development experience in those languages.

How would you validate network segmentation automatically?

What they are checking: The posting names segmentation validation specifically.

How do you integrate with ServiceNow or Splunk in an event-driven way?

What they are checking: The posting names ServiceNow, Jira, Splunk, Sentinel, GitHub and Azure DevOps integration.

How do you handle secrets in automation?

What they are checking: The posting names secrets-management platforms, and hardcoded credentials are the usual failure.

Practice this interview out loud.

Offer builds a real interview for this exact role at Wintrust from your resume and this job description, asks the questions one at a time, and tells you what landed. The first one is free.

Practice this out loud

The full job description

As published by Wintrust.

Wintrust provides community and commercial banking, specialty finance and wealth management services through its 16 bank charters and nine non-bank businesses. Wintrust delivers the sophisticated solutions of a large bank while staying true to the relationship-focused, personalized service of our community banking roots. We serve clients in all 50 states with more than 200 branch banking locations in Illinois, southwestern Florida, northwestern Indiana, west Michigan and southern Wisconsin and commercial banking offices in Chicago, Denver, Milwaukee, Grand Rapids, Mich., and in key branch banking locations throughout Illinois. Our people are the heart of our business and we are proud to rank consistently as a top place to work. Wintrust is a $66 billion financial institution based in Rosemont, Illinois, and listed on the NASDAQ Global Select Market under the symbol “WTFC.” Why join us? • An award-winning culture! We are rated a Top Workplace by the Chicago Tribune (past 12 years) and Employee Recommended award by the Globe & Mail (past 6 years) • Competitive pay and discretionary or incentive bonus eligible • Comprehensive benefit package including medical, dental, vision, life, a 401k plan with a generous company match and tuition reimbursement to name a few • Promote from within culture Why join this team? • This position has the opportunity to interface with and have a positive impact on multiple areas of Wintrust's business • We hold ourselves accountable to high standards, share wins, operate ethically, and have fun Position Overview Wintrust's Network Security is looking to hire a seasoned network security automation engineer to join our team. This role will focus on reducing manual network security configuration activities, configuration drift and ensuring security control effectiveness. The Senior Network Security Automation Engineer is responsible for engineering secure and repeatable automation capabilities across enterprise network and security platforms. What You’ll Do • Build reusable automation modules and engineering patterns for firewalls, routers, switches, load balancers, VPN platforms, DNS, cloud networking, network segmentation, and secure connectivity services. • Automate network security controls, including firewall-policy deployment, segmentation validation, access-rule analysis, configuration compliance, egress filtering, and identification of overly permissive or unauthorized network paths. • Integrate network automation into CI/CD pipelines, incorporating code reviews, automated testing, security scanning, approval gates, version control, and rollback capabilities for network and security configuration changes with incumbent technologies. • Develop automated compliance and configuration-drift monitoring to compare deployed infrastructure against approved architecture, security baselines, policy requirements, and authoritative configuration repositories. • Design and develop network automation solutions using Python, PowerShell, APIs, infrastructure-as-code, and orchestration frameworks to automate network provisioning, configuration, validation, and remediation. Qualifications • 7+ of experience in network engineering, network security, platform engineering, automation, or a related technical discipline • Advanced knowledge of enterprise routing, switching, firewalls, load balancing, VPN, DNS, network segmentation, and hybrid connectivity. • Strong development experience with Python, PowerShell, or comparable automation languages. • Experience integrating network and security platforms through REST APIs, SDKs, webhooks, and event-driven workflows. • Experience integrating with ServiceNow, Jira, Splunk, Microsoft Sentinel, GitHub, Azure DevOps, or secrets-management platforms. Benefits Medical Insurance • Dental • Vision • Life insurance • Accidental death and dismemberment • Short-term and long-term Disability Insurance • Parental Leave • Employee Assistance Program (EAP) • Traditional and Roth 401(k) with company match • Flexible Spending Account (FSA) • Employee Stock Purchase Plan at 5% discount • Critical Illness Insurance • Accident Insurance • Transportation and Commuting Benefits • Banking Benefits • Pet Insurance Compensation The estimated salary range for this role is $117,000.00 - $158,000.00, along with eligibility to earn an annual bonus. Actual salaries may vary based on several factors, such as a candidate’s qualifications, skills and experience. #LI-Hybrid #LI-JB1 From our first day in business, Wintrust has been proud to serve a variety of unique communities and people from all walks of life. To build a company that reflects the communities we serve, we believe that fostering a unique and inclusive workplace where everyone feels valued and empowered to succeed will support our ongoing success. Wintrust Financial Corporation, including community banking and financial services subsidiaries, is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, age, national origin, disability, veteran status, genetic information, and other legally protected categories.