Fellows Directory

Bailey Moore

Wintrust Ventures

Bailey Moore is Managing Director at Wintrust Ventures, a division of Wintrust Financial Corporation. Wintrust Ventures is an early-stage investment fund focused on emerging growth businesses in Illinois, Wisconsin, and Northwest Indiana. While the fund is industry agnostic, Bailey’s focus is primarily digital marketplaces, digitally native brands, and enterprise software. Since founding Wintrust Ventures, Bailey has been responsible for 55 investments in 34 companies. Wintrust Ventures portfolio companies represent a combined $500M raised to date and $350M in total revenue last year.

Previously, Bailey was able to acquire insights into the formation and rapid growth of Chicago’s middle market as part of the original team of Wintrust Commercial, which grew from $0 to over $3B in assets under management during her tenure.

Bailey started her career at Alaris as a liquidation and bankruptcy consultant, working on restructurings for Comerica and GE Finance during the 2008 recession.

Education, Personal, and Fellowship

Bailey holds a BS in business management and finance from Purdue University. In 2015, she was voted as one of Crain’s Chicago Business 20 top professionals in their 20s and has been featured in various print and online publications.

Bailey is serving her fellowship at Wintrust Ventures as a member of Class 24. Her mentor is Bret Maxwell, General Partner of MK Capital.