President & CEO

Over the span of his 20+ year career in financial services, Ryan Bailey has built a standout reputation for enhancing customer experiences at every turn. His strong retail background, combined with a forward-looking approach to digital strategy, makes him the ideal choice to lead Cambridge Savings Bank as our new President & CEO.

Ryan’s leadership promises to uphold our esteemed legacy and reputation, while forging new paths to ensure we remain at the forefront of customer satisfaction, continue to drive digital innovation, and deepen our engagement with the communities we serve, all while preserving the fabric of our culture.

Before joining our team at 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 employees. Under his leadership, Ryan 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, his wife Melissa, and their three children, Taylor, Duncan, and Griffin, have recently moved from San Antonio to Boston. This transition feels like a return to roots, given their extended family's presence in New England. The Baileys also have a passion for sports, with Ryan taking an active role in coaching his children's football teams. Although he currently favors the Detroit Lions, it seems inevitable that his loyalty will soon shift towards the New England Patriots, embracing his new home's local spirit.