Employer-funded program helps employees in recovery seek pardons or expungements of long-ago criminal convictions

Nine years into recovery, Cindy Raymond has earned a master’s degree and built a career, leading a team guiding others through some of the most vulnerable moments of their lives.

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Cindy Raymond receives her Second Chance Scholarship, which will support her efforts to clear a decades‑old criminal record.

Yet the mistakes she made at 21 still shape her life at 48. Because those mistakes led to a criminal record, they influence where she can live, where she can work, and whether she can vote, or obtain professional licensure.

“I’ve done everything right,” Raymond said. “I’ve paid my debt to society. I have a career. I pay my taxes. And still, I’m asked to jump through hoops of fire.”

In the fifteen years since she last faced new charges, Raymond has sought to clear her record. She has spent years navigating a process of seeking to have arrest or conviction records sealed or expunged or, ultimately, requesting a pardon. Raymond has navigated a maze of county-by-county rules, legal fees, and administrative hurdles, often forced to repeatedly explain offenses from her early twenties.

Millions forego clearing their records because of barriers.

Raymond now has a partner in this effort, her employer of three years, Wayspring, a Nashville-based company supporting individuals impacted by substance use disorder. Wayspring has launched Second Chance Scholarships, a first-of-its-kind employer-funded initiative designed to help their employees in recovery navigate the legal and financial barriers tied to past criminal records. Raymond is one of three initial recipients of a Second Chance Scholarship.

Raymond is hardly alone in her experience seeking to clear her record. Research shows that 25 to 30 million Americans qualify to have an arrest or conviction record sealed or expunged, according to JPMorgan Chase’s PolicyCenter report on automatic record clearing. Yet only about 6.5 percent of those legally eligible obtain expungement within five years, a study published in the Harvard Law Review found. For many, the process is too confusing, costly, or inaccessible to navigate alone.

‘People are more than their past’

Wayspring has long considered itself a company of second chances. While hiring remains merit-based, the organization does not automatically exclude individuals in recovery or those with criminal justice involvement. Instead, it recognizes that lived experience can build trust and inspire the members it serves.

“We believe people are more than their past,” said Carter Paine, Chief Executive Officer at Wayspring. “That belief extends beyond the members we serve to our own team. When someone has stayed substance-free, built stability, and found ways to give back, we want to celebrate that growth.”

Launched during National Recovery Month in September 2025, the Second Chance Scholarship program provides financial support for expungements and pardons, along with guidance through complex legal processes. Applicants are evaluated by Wayspring’s Criminal Justice Committee and assessed on accountability, personal growth, and commitment to supporting others.

In its first year, three employees applied. All three were awarded scholarships. Raymond was one of them.

“Not everyone starts life with the same opportunities,” said Tanya Deane, Chief Human Resources Officer at Wayspring. “Second chances should be possible for anyone willing to make a change. This program helps remove barriers that can haunt people for decades and gives them a fair shot at moving forward.”

For Raymond, receiving the scholarship marked a turning point.

“I just started crying,” she said. “The feeling was…freedom. Knowing that this final thing from my past wouldn’t weigh me down anymore. That the sky is the limit.”

About Wayspring

Wayspring is advancing the treatment of substance use disorder for health plan members, guiding them toward a better life and lasting recovery. We partner with health plans to manage and care for this population through our whole-person care model, addressing physical, behavioral, and social needs alongside treatment. We also support provider networks with valuable insights and strategies to enhance care quality.

This is recovery made right — with support that shows up.

Learn more at Wayspring.com. Wayspring members can visit MyWayspring.com for resources and support.

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The feeling was…freedom. Knowing that this final thing from my past wouldn’t weigh me down anymore. That the sky is the limit.