Senior Insider Risk Investigator

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