2025 Speakers

Paul H. Richardson, Jr. is the Founder and CEO of Tumbleweed Vida, Inc., an InsurTech platform helping families navigate caregiving, legacy planning, and policyholder engagement with clarity and compassion. With over two decades of experience in healthcare, education, and technology, Paul has held leadership roles across national health systems and Fortune 10 companies, managing large-scale operations, strategic planning initiatives, and organizational change efforts.

Prior to launching Tumbleweed, Paul served as an executive facilitator and coach, guiding C-suite teams through enterprise transformation, employee experience strategy, and innovation planning. He has designed and led national learning events, facilitated annual strategy sessions, and advised on distribution models in highly regulated industries.

As a founder, Paul brings lived experience as a caregiver and a bold vision for reimagining how insurance carriers engage with today’s aging population. He has led Tumbleweed through top accelerators including the Global Insurance Accelerator and NMotion powered by gener8tor, and recently launched a carrier partnership with Wellabe, integrating Tumbleweed into their member rewards platform.

Paul’s work sits at the intersection of innovation, empathy, and impact—transforming legacy systems by putting people first.