Waypoint Group Leadership
Ryan Caldwell
Ryan Caldwell
Ryan Caldwell
Ryan is a senior leader and Partner known for building resilient, future-ready organizations. With 10+ years of experience across the fintech and enterprise risk sectors, Ryan helps executive stakeholders navigate volatility through disciplined operational strategy and crisis management.
Ryan’s approach is defined by "Value-Driven Resilien
Ryan is a senior leader and Partner known for building resilient, future-ready organizations. With 10+ years of experience across the fintech and enterprise risk sectors, Ryan helps executive stakeholders navigate volatility through disciplined operational strategy and crisis management.
Ryan’s approach is defined by "Value-Driven Resilience"—ensuring that risk management isn't just a defensive measure, but a competitive advantage. He is a veteran of global crisis response, having successfully scaled continuity programs in some of the most demanding environments in the industry.
A graduate of Boston University (MA) and Virginia Commonwealth University (BA), Ryan resides in Jupiter, FL. Outside of the boardroom, he is an active member of his community, coaching youth sports and enjoying the Florida outdoors with his family.
Ray Cooney
Ryan Caldwell
Ryan Caldwell
Ray is a results-driven procurement and operations leader with a 15-year track record of strengthening performance for large-scale enterprises. As a Partner, Ray bridges the gap between high-level business acumen and the tactical rigor required to execute multimillion-dollar strategies.
Ray’s expertise was forged in the U.S. Army and refin
Ray is a results-driven procurement and operations leader with a 15-year track record of strengthening performance for large-scale enterprises. As a Partner, Ray bridges the gap between high-level business acumen and the tactical rigor required to execute multimillion-dollar strategies.
Ray’s expertise was forged in the U.S. Army and refined in the C-suite. He is recognized for his ability to consolidate enterprise purchasing and negotiate large-scale contracts that drive significant fiscal impact. Whether leading a crisis response or driving a global sourcing strategy, Ray leads with integrity and a focus on building systems that improve compliance and efficiency.
Ray holds a deep passion for building motivated teams, a trait reinforced during his years in uniform and as an entrepreneur. He resides in Jacksonville, FL, where he enjoys coaching his children’s football and baseball teams and exploring the local coast.