Stephen Crossman

Stephen Crossman serves as President and Chief Revenue Officer of ILS, where he leads global commercial strategy, go-to-market execution, and growth initiatives, with a singular focus on giving plaintiff attorneys the discovery capabilities and technological edge they need to compete on equal footing with the defense.

A licensed attorney and Chicago-Kent College of Law graduate, Stephen brings more than 20 years of executive leadership experience across legal technology and B2B services. He is known for translating strategy into execution — building disciplined, data-driven revenue organizations that are as customer-centric as they are results-oriented. Stephen has served as Chief Revenue Officer and Chief Sales Officer at SurePoint Technologies, CourseKey, and BERA.ai, and has led major legal division sales at Bloomberg BNA and Thomson Reuters.

His track record includes guiding SurePoint Technologies to an 11x revenue exit under private equity ownership and consistently building high-performing commercial teams across companies of all sizes and growth stages.

Stephen joined ILS because the mission resonates with him. As a licensed attorney, he treats every client as a trusted partner who understands their work, their cases, and the stakes — not just their budget. He holds a B.A. from the University of Iowa and a J.D. from Chicago-Kent College of Law.