Kelly Drouillard has over 25 years' experience in finance, operations, and strategic development. She has led a career marked by continued growth, holding senior level positions. Kelly has been intricately involved in the insurance industry and commercial M&A for many years. She develops strategic acquisition and capital practices, provides sell-side representation, and consulting consulting to small to mid-sized businesses.

Kelly’s background is primarily in insurance and also in early-stage companies in a variety of industries. She is a CPA and CPCU. Transaction experience includes various M&A deals, debt financing structures and private equity investments. With a passion for entrepreneurs and economic development, Kelly was an early member of Womens Capital Connection (WCC) and Mid America Angels. Kelly has participated in several angel capital investing programs including valuations, exits, and due diligence. Kelly was a panelist for an Equity Matters event sponsored by Springboard. She is a former executive committee member of WCC.

A graduate of Kansas State University, Kelly’s career began in 1987 with KPMG in the Kansas City office. She has held various positions in financial services, consulting and the insurance industry including owning her own firm for 4 years. She joined Oak Street Funding in 2012 under private equity ownership, and then founded specialty lending vertical Live Oak Bank 2015-2022. Kelly is now an independent consultant providing sell-side and buy-side representation and niche consulting services.

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