Bailey Moore is the Co-founder and Managing Director of Wintrust Ventures, a division of Wintrust Financial Corporation. See sector focus and contact routes.
Bailey Moore is the Co-founder and Managing Director of Wintrust Ventures, a division of Wintrust Financial Corporation, where she oversees an early-stage fund focused on emerging growth businesses in Illinois, Wisconsin, and Northwest Indiana. Her personal investment thesis targets digital marketplaces, digitally native brands, and enterprise software within these Midwest geographies, while the broader fund remains industry agnostic. Wintrust Ventures typically invests in late-stage Seed and Series A rounds and acts as a preferred lender for venture-backed companies in the region. Since founding the venture arm, Moore has been responsible for 82 investments across 35 companies. Notable portfolio companies include Rippleshot, a network management software firm where Moore also invested personally as an angel investor in August 2018. While the fund supports Chicago’s innovation community including start-ups and incubators, Moore’s specific focus distinguishes her from the broader industry-agnostic strategy. She holds a BS in business management and finance from Purdue University and was recognized in 2015 as one of Crain’s Chicago Business 20 top professio
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