Samuel Poole

Samuel Poole

Chief Retail Officer Chesapeake Bank
Samuel Poole
Samuel G. Poole is a Senior Vice President & Chief Retail Officer at Chesapeake Bank in Virginia. He shares close to 30 years of banking experience with his team, customers and community. He earned his A.S. in Education from Becker College in Worcester, Ma. Sam is a 2004 graduate of the VBA Virginia Bankers School of Bank Management where he served as Class Vice President. He graduated in 2013 from LEAD Historic Triangle, a Greater Williamsburg Chamber & Tourism Alliance sponsored program. He also earned his Gallagher Center for Leadership Certification in 2016. In 2019 he completed The Center for Creative Leadership’s Leadership Development Program and graduated from The Virginia Banker’s Association Executive Leadership Institute. He is also a 2024 graduate of the Stonier Graduate School of Banking and carries a Wharton Leadership Certificate. Sam currently serves on the Board of Directors for LEAD Greater Williamsburg and The United Way of Greater Peninsula Virginia. He is a former Board member of The Relationship Foundation of Virginia, past Board Chair of The Greater Williamsburg United Way and former Treasurer and Executive Committee member of the R. F. Wilkinson YMCA Board of Directors.

Building for Growth - Human Centered and Innovative Branches

2:00 PM Panel: Adding AI to Your Day-to-Day— Use Cases, Governance, and Team Readiness

Artificial intelligence is no longer confined to innovation labs or isolated pilots—it is increasingly being asked to prove enterprise-wide value across retail banking. This panel explores where banks and credit unions are moving beyond experimentation to deployment. Leaders will discuss how they determine which use cases are valuable, how success is measured, and what organizational conditions are required for AI adoption to move from promising to practical. The conversation will also examine what internal resistance still exists, and how institutions build internal expertise and team readiness.

Hear how others are working to:

  • Identify which AI use cases are producing measurable returns today  
  • Evaluate how leading institutions decide what moves beyond pilot stage  
  • Understand what operating models support sustainable AI deployment
  • Apply lessons for aligning AI initiatives with business priorities

Creating Trust and Loyalty Through CX and Connected Culture

3:10 PM Panel: Next-Up Leaders: Growing Talent from Within

Strong leadership pipelines do not happen by accident; they are built through intentional development, early identification of talent, and deliberate opportunities for growth before succession becomes urgent. As banks and credit unions face ongoing change in workforce expectations, retirements, and expanding skill requirements, developing future leaders early has become a strategic priority rather than a long-term aspiration. This session explores how institutions can create meaningful leadership pathways, and foster confidence to step into larger roles with confidence. Speakers will share how they are moving beyond traditional succession planning to build leadership readiness.

Leave with practical ideas for: 

    • Identifying talent earlier and aligning development to future organizational needs  
    • Creating practical leadership pathways that extend beyond formal succession plans  
    • Expanding practice through mentoring, cross-functional work, and more 
    • Strengthening retention by showing employees a visible path to growth 

    Check out the incredible speaker line-up to see who will be joining Samuel.

    Download The Latest Agenda