Senior Insider Risk Investigator

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 $66billion financial institution based in Rosemont, Illinois, and listed on the NASDAQ Global Select Market under the symbol "WTFC".

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.

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.

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.

• 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.

• 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 endpoints, cloud, collaboration, email, identity, and data protection platforms.
• Experience preparing executive‑ready…