About Debra Livingston

ReEmployAbility CEO & Founder

Debra Livingston has served in various executive capacities throughout her career, with a concentrated focus on return-to-work programs. With over 25 years of workers’ compensation experience, she started her career as a claims adjuster and moved into various facets of the industry including, account executive for Aetna Property Casualty, broker consultant for Wells Fargo Insurance Services, and director of claims for a large Florida professional employer organization.

When Debra started ReEmployAbility more than 20 years ago, she didn’t realize she would have the opportunity to impact so many lives. Today, the Transition2Work program has helped thousands of injured workers, individuals who are typically concerned and uncertain about their lives after having experienced an injury.

Through ReEmployAbility, she works with clients to advocate for their employees and to encourage a more empathetic and supportive approach during the return-to-work process. By joining business and community, ReEmployAbility has provided volunteers to thousands of nonprofit organizations across the US who have contributed over 21 million hours of community service!

Debra is a contributing faculty member at Work Comp College and an active member of the RTW Breakout Committee for WCI. She is the immediate past chair of the Board of Directors for The Spring of Tampa Bay, a nonprofit dedicated to preventing domestic violence, supporting victims, and fostering transformative change in families and communities.

Debra has been recognized as one of the Top 25 Entrepreneurs of Tampa Bay (2024) and a Top Women Leaders – Women We Admire (2024). Her accolades include the Tampa Bay Business & Wealth Magazine – Women Who Win (2025), BLOOM Magazine Excellence Award for Leadership (2024), Tampa Bay Times Top Workplaces Leadership Award (2024), Tampa Bay Business Journal Business Woman of the Year (2019), and Business Insurance Woman to Watch (2017). She is also a recipient of the Comp Laude Magna Comp Laude Award (2023) and the People’s Choice Award (2021), further solidifying her reputation as an influential leader and advocate in her field.