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 more than 25 years of workers’ compensation experience, she began 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 founded ReEmployAbility in 2003, she did not anticipate the far‑reaching impact the organization would have. Today, ReEmployAbility is a national leader in transitional employment, partnering with more than 52,000 nonprofit organizations through its Transition2Work® program, which has helped thousands of injured workers who are often concerned and uncertain about life following an injury.

Through ReEmployAbility, Debra works closely with clients to advocate for injured employees and encourage a more empathetic, supportive return‑to‑work process that provides structure and purpose during recovery. By joining business and community, the Transition2Work program has generated more than 23 million volunteer hours, reduced employer indemnity costs, and created millions in community economic value nationwide.

Debra is widely recognized as a thought leader and advocate for improving the return‑to‑work experience. She is a contributing faculty member at WorkCompCollege.com, an active member of the WCI Return‑to‑Work Breakout Committee, and a frequent speaker at industry conferences, panels, and webinars. She also shares leadership insights through her LinkedIn newsletter, Direct From Deb.

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 Women Who Win (2025), 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.