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.”

• 7+ years of experience in cybersecurity, insider risk, investigations, threat intelligence, digital forensics, incident response, security operations, corporate investigations, or related disciplines.

• 5+ years of experience conducting investigations involving data loss, insider threats, employee misconduct, fraud, abuse of access, policy violations, or other human-centric security risks.

• Experience managing complex investigations from initial intake through evidence collection, analysis, stakeholder engagement, reporting, and remediation.

• Experience working with Data Loss Prevention (DLP), Insider Risk Management, SIEM, UEBA, eDiscovery, digital forensics, or related investigative technologies.

• Demonstrated experience analyzing and correlating technical, behavioral, and business-context data to assess risk and support investigative findings.

• Experience investigating activity across endpoint, cloud, collaboration, email, identity, and data protection platforms.

• Experience preparing executive-ready investigative reports, risk assessments, and case summaries for technical and non-technical audiences.

• Strong understanding of insider threat methodologies, data protection principles, and human-centric security risks.

• Experience conducting threat hunting activities and identifying emerging patterns, trends, and risks through proactive analysis.

• Demonstrated ability to mentor, coach, or provide investigative guidance to peers, analysts, or investigators.

• Experience operating within highly regulated industries and managing sensitive or confidential employee-related information

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 Insider Risk Investigator serves as the lead investigator for the Insider Risk Program, responsible for leading complex investigations involving data loss, insider threats, policy violations, misuse of company assets, and emerging AI-related risks. This role partners closely with Legal, Human Resources, Privacy, Cybersecurity, and business stakeholders to assess risk, drive appropriate response actions, mentor fellow investigators, and support the continuous maturation of the Insider Risk Program.

What You’ll Do

Lead complex insider risk and data loss investigations across email, endpoint, cloud, collaboration, and AI-enabled technologies
Analyze technical, behavioral, and business context to assess risk, intent, and potential impact
Coordinate investigation activities and remediation actions with Legal, Human Resources, Compliance, Privacy, and Cybersecurity teams
Conduct proactive threat hunting activities to identify high-risk behaviors, emerging insider threats, and unauthorized data exposure
Research emerging insider threat, data protection, and AI-related risks to enhance investigative effectiveness and partner with Insider Risk Engineering team to identify monitoring gaps, provide investigative feedback, and improve alert fidelity
Identify opportunities to improve visibility into human-centric risks and strengthen investigative capabilities
Serve as the lead investigator for the Insider Risk Program, providing guidance and mentorship to other investigators sharing investigative knowledge, lessons learned, and emerging threat insights with the team

Qualifications

7+ years of experience in cybersecurity, insider risk, investigations, threat intelligence, digital forensics, incident response, security operations, corporate investigations, or related disciplines
5+ years of experience conducting investigations involving data loss, insider threats, employee misconduct, fraud, abuse of access, policy violations, or other human-centric security risks
Experience managing complex investigations from initial intake through evidence collection, analysis, stakeholder engagement, reporting, and remediation
Experience working with Data Loss Prevention (DLP), Insider Risk Management, SIEM, UEBA, eDiscovery, digital forensics, or related investigative technologies
Experience investigating activity across endpoints, cloud, collaboration, email, identity, and data protection 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 $150,000.00 - $165,000.00, 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.