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Rick Pleczko serves as the CEO of the Operating Executive Group at The CapStreet Group since June 2021, focusing on enhancing value across portfolio companies. Pleczko holds multiple executive chair positions at hh2 Cloud Services, Informativ, SmartSights, and TradePending, and is a board member and executive chair at symplr, where notable leadership as President and CEO has shaped the company's direction in healthcare operations. Additionally, Pleczko functions as Vice Chair at FinThrive and remains actively engaged as a board member and trustee at Grissom Air Museum, overseeing entrepreneurial initiatives as a judge in the Ernst & Young Entrepreneur of the Year Program since January 2018. Educational backgrounds include attendance at WR Tuson and Fulwood High between 1975 and 1977.