Over the span of his 20+ year career in financial services, Ryan Bailey has focused on enhancing customer experiences and supporting communities at every turn.

Prior to becoming President and CEO of CSB, Ryan held leadership positions at some of the country’s most respected financial institutions, including TD Bank, Bank of the West, JP Morgan Chase, Fifth Third Bank, and Bank of America. His most recent role was as the Head of Retail Banking at USAA, where he led a team of nearly 2,000 customer-focused employees and spearheaded initiatives to deliver world-class products and services to the military community and their families, setting a benchmark for excellence.

Ryan holds a Master of Business Administration and a Bachelor’s degree in Business Administration with a focus on Finance from Western Michigan University. Additionally, his active engagement in the Consumer Bankers Association, notably as the former Chair of the Board, underscores his significant contributions and commitment to advancing the industry.

Ryan and his wife, Melissa, are proud parents of their three children, Taylor, Duncan, and Griffin. The Baileys also have a passion for sports, with Ryan taking an active role in coaching his children's football teams.

Over the span of his 20+ year career in financial services, Ryan Bailey has focused on enhancing customer experiences and supporting communities at every turn. Prior to becoming President and CEO of CSB, Ryan held leadership positions at some of the country’s most respected financial institutions, including TD Bank, Bank of the West, JP Morgan Chase, Fifth Third Bank, and Bank of America. His most recent role was as the Head of Retail Banking at USAA, where he led a team of nearly 2,000 customer-focused employees and spearheaded initiatives to deliver world-class products and services to the military community and their families, setting a benchmark for excellence. Ryan holds a Master of Business Administration and a Bachelor’s degree in Business Administration with a focus on Finance from Western Michigan University. Additionally, his active engagement in the Consumer Bankers Association, notably as the former Chair of the Board, underscores his significant contributions and commitment to advancing the industry. Ryan and his wife, Melissa, are proud parents of their three children, Taylor, Duncan, and Griffin. The Baileys also have a passion for sports, with Ryan taking an active role in coaching his children's football teams.

CEOs You Should Know is iHeartMedia Boston's showcase of businesses that drive New England's regional economy. Hear from key business leaders who contribute to the vibrant and growing community.

CEOs You Should Know - Boston

Over the span of his 20+ year career in financial services, Ryan Bailey has focused on enhancing customer experiences and supporting communities at every turn.

Prior to becoming President and CEO of CSB, Ryan held leadership positions at some of the...