Kendra Castelloni is Co-Chief Executive Officer of Wintrust Private Client and has over 25 years of experience in financial services. She is responsible for managing the group’s efforts throughout Wintrust’s footprint, facilitating work with high-net worth individuals, families, and organizations, including closely-held and family-owned businesses. Kendra assists in leveraging the extensive resources and highly skilled professionals at Wintrust to present best-in-class solutions to help clients accumulate, preserve, grow, and transfer their wealth.  

Prior to her current role, Kendra served as President of Northbrook Bank & Trust, a Wintrust Community Bank. Early in her career, Kendra was with American National Bank, LaSalle Bank, and JPMorgan Chase where she served in various private banking and team lead roles. 

As a Chicago area native, Kendra strives to give back in various ways. She currently sits on the Board of Directors of Bear Necessities Pediatric Cancer Foundation, and previously served on the Board of the Northbrook Chamber of Commerce and co-chaired the March of Dime’s Signature Chef’s Auction event. 

Kendra earned a bachelor’s degree in finance from Eastern Illinois University. She attended on a Division I athletic scholarship for soccer where she served as captain of the team her senior year. She holds a Series 7 and Series 63 securities licenses. She enjoys attending her kids’ many sport activities, traveling, and playing golf. Kendra and her husband, Dave, live in Palatine with their two children.