Jobs › Wintrust

Cybersecurity Senior Architect

Wintrust · Rosemont, IL · $140,000–$180,000 a year · Full time

Posted Jul 8, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

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

About your past

Tell me about a time you convinced leadership to invest in a security improvement.

What they are checking: Whether they can explain risk in business terms to win funding and support.

How do you work with engineering teams so security is built in from the start?

What they are checking: Whether they partner with builders early instead of acting as a final gate.

What would you do

A business team wants to launch a new cloud app next month, but it hasn't had a security review. What do you do?

What they are checking: Whether they can enable the business with a fast, risk-based review instead of just blocking it.

How do you decide which security risks to fix first?

What they are checking: Whether they prioritize by impact and likelihood rather than chasing every alert.

About the work

Walk me through how you'd design a security architecture for a bank with more than 200 branch locations.

What they are checking: Whether they can think at enterprise scale about segmentation, identity and monitoring across many sites.

How would you apply zero trust principles in a bank with many legacy systems?

What they are checking: Whether they can move toward zero trust in practical steps instead of a rip-and-replace plan.

How do you design identity and access management for employees, contractors and service accounts?

What they are checking: Whether they understand that identity is a key control and handle privileged access carefully.

How do you align security architecture with regulations like FFIEC guidance and GLBA?

What they are checking: Whether they know the rules banks must follow and build them into designs.

How would you protect the bank against ransomware?

What they are checking: Whether they think in layers, from prevention to detection to recovery, including tested backups.

How do you manage third-party risk for vendors that connect to the bank's network?

What they are checking: Whether they understand vendor access is a major attack path and design controls for it.

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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 10 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 • Family-friendly work hours • With 175+ community bank locations, we offer opportunities to grow and develop in your career • Promote from within culture Why join this team? • We have a culture that encourages an entrepreneurial spirit • We offer multiple opportunities for development and upward mobility Job Description Summary Cybersecurity Cloud Architect at Wintrust is a technical leadership role to develop strategic and technical solutions to drive maturity of Wintrust’s Cloud environments. As a Cybersecurity Cloud Architect, you will be responsible for reviewing, validating and guiding implementation of cloud native or 3rd party security controls across all business units at Wintrust. You will work with business leaders, infrastructure and development organizations, and risk and governance to infuse information security controls into business and technology processes. In addition, you will lead development of threat modeling for SaaS and PaaS based products and services to identify risk and participate in architectural reviews of products in internal development and 3rd party providers. What You’ll Do • Lead cloud-centric Information Security strategy to meet Wintrust strategic growth goals • Research and lead design of cloud-based security solutions with the Wintrust product and services offerings across all business units, drive cloud security and support a security strategy tailored to enterprise needs • Advise Wintrust business units on how to implement identity and access for SaaS and PaaS Wintrust users and 3rd party partners, including registration, authentication, authorization, administration, audit, and reporting. • Guide i ntegration of modern authentication and authorization security controls into Wintrust IaaS and PaaS platforms, 3rd party SaaS, and integrated multi-vendor environments. • Serve as a subject matter expert on SaaS, PaaS and IaaS technologies and security with responsibilities to ensure enablement of robust security controls • Lead development of cloud security assessment program to identify cloud-based vulnerabilities and threat; develop mitigation plans to address identified security gaps. Adapt hands-on approach with the Wintrust products and services implementation to define and deliver information security requirements and architectural solutions Qualifications • 5+ years of relevant architect experience • Bachelor’s degree or equivalent experience • Cloud experience (Azure preferred, AWS) • Certifications: Azure, Microsoft, AWS, Data Science • Banking experience strongly preferred 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 $140,000.00 - $180,000.00, 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 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.

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