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
The Senior Data Loss Prevention Engineer is responsible for the design, implementation, and continuous improvement of Wintrust’s enterprise DLP control framework across on-premises, cloud, endpoint, email, and web environments. This role serves as the technical authority for DLP engineering, leveraging platforms such as Proofpoint, CrowdStrike, and ServiceNow to drive high-fidelity detections, automation, and scalable policy design. The Senior DLP engineer is accountable for measurably improving the maturity, effectiveness, and business alignment of Wintrust’s data protection program, including data classification and AI policy usage.
What You’ll Do
Design, deploy, and maintain DLP controls across multiple platforms, such as: Microsoft Purview, Proofpoint DLP, and CrowdStrike.
Engineer custom DLP detections using regex, EDMs, IDMs, classifiers, and contextual telemetry across email, endpoint, and cloud channels.
Own DLP policy lifecycle management, including creating, normalization, versioning, tuning, testing, and structured change management.
Continuously improve detection fidelity to reduce false positives and increase high-confidence alerts.
Tune and correlate detection across multiple platforms to improve signal quality.
Build and optimize automation pipelines to centralize DLP telemetry for investigation teams.
Configure alerts, workflows, and dashboards to enhance visibility into user behavior, endpoint activity, and data movement.
Qualifications
Bachelor’s degree required
7+ years in information security with 5+ years focused on DLP, data protection, or insider risk engineering
Hands-on experience with Proofpoint DLP and CrowdStrike in an enterprise environment
Experience operating DLP programs within financial services or regulated industries strongly preferred
Experience supporting M&A integrations, multi-tenant environments, or complex organizations 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 $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.
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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.