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Creating Opportunities for Second Chance Hiring

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This week, the MIT Sloan School of Management will host business luminaries from Nike, Intel, Kroger, Union Pacific, and other major companies for the “Writing the Code: Second Chance Hiring” conference. And it all came about due to a collaboration between students and staff at the MIT Sloan Office of Diversity, Equity, and Inclusion and the Career Development Office.

“If you look at the companies who are coming to this conference, and the number of employees they represent in the United States alone, then this is one of the biggest conferences of the year at MIT Sloan, and it’s about second chance hiring,” says EMBA candidate Daniel Dart.

The United States Chamber of Commerce defines second chance hiring as “the practice of hiring individuals with a criminal record.” Additionally, the business advocacy group describes it as an altruistic and economically beneficent business practice, noting that it can provide opportunities to millions of Americans whose arrest or conviction records often create significant economic and social barriers.

Daniel Dart | EMBA candidate, General Partner at Rock Yard Ventures
We have an outsized ability to influence so much, as my fellow MIT Sloan students are going to be in leadership positions one day.

“When we think about the future of work, we tend to think about technology and how it changes everything, yet we have over 70 million individuals in the U.S. with a record. It is incredibly important that we consider those who have been pushed out,” says conference organizing committee member Brooke Wages, MBA ’22.

Dart, a formerly incarcerated individual who earned degrees from the London School of Economics and founded the venture capital firm Rock Yard Ventures, has become a fierce advocate for second chance hiring.

“This isn’t an anomaly,” he says. “It’s a big issue that people care about, and I think that businesses and business schools should be thinking about it, too.”

Sustainable, thriving communities

While working at his family’s recycling business, James Repenning, MBA ’02, hired and befriended a man named Angelo. At the time, Angelo was living in a halfway house after being paroled from a life sentence.

“He was a fantastic employee, super loyal, and the first guy in every morning. We’re still friends today,” says Repenning, who was inspired to provide the same opportunity for others but was unsure how to proceed.

Over 20 years later, shortly after serving as president of Floyd’s 99 Barbershops, a national chain, Repenning received a Facebook message from the film producer Scott Budnick of The Hangover fame. Budnick, founder of the Anti-Recidivism Coalition, needed help getting licenses for barbers in the California prison system.

The chance collaboration rekindled Repenning’s desire to help others like Angelo. It also sparked an idea: R&R Head Labs, a new barbershop he founded in Denver, Colorado, that features justice-impacted barbers and stylists.

Brooke Wages | MBA ’22, Associate at McKinsey & Company
It is incredibly important that we consider those who have been pushed out.

“Getting these men and women back on their feet feels good and is itself enough of a reason to do so, but I also saw a huge business opportunity specific to barber shops,” he says. “They are a labor pool with tons of relevant experience, in a country that is short on barbers.”

Repenning, who will be moderating a panel at this week’s conference, is excited for current MIT Sloan students to have the chance to think about how they might incorporate second chance hiring into their strategy much earlier in their careers than he did.

“That’s a huge difference that has the potential to greatly benefit formerly incarcerated people and the communities they are returning to,” says Repenning. “I’m proud to see MIT leading the charge because this is about more than good business—it leads to sustainable and thriving communities.”

Championing second chance hiring

The brainchild of Steven Branch (Senior Associate Director, Diversity, Equity, and Inclusion, Career Development Office), the Writing the Code programming series at MIT Sloan centers diverse perspectives and impacts as they relate to the career journeys of underrepresented minority students and alumni. Past events include panels on everything from entrepreneurship and salary negotiation, to repeat events highlighting the networking potential of golf.

As Dart progressed through the first year of his EMBA curriculum in 2023, Branch separately attended another conference about second chance hiring and realized the educational potential for implementing a similar drive at MIT Sloan.

“What are we doing currently in our space now? Who are the champions we have? Do we have anybody that’s doing research on this?” he recalled asking himself at the time.

After Branch and Dart met and began comparing notes, the MIT Sloan event quickly came together. The pair joined forced with Wages—as well as Ken Oliver, vice president of corporate social responsibility at Checkr, and Jeff Korzenik, chief economist at Fifth Third Bank—to organize the conference and attract big names and companies to sign on.

James Repenning | MBA ’02, CEO of R&R Head Labs
This is about more than good business—it leads to sustainable and thriving communities.

And sign on they did, for Writing the Code’s featured speakers include Larry Miller, chairperson of the Michael Jordan brand at Nike and former president of the Portland Trailblazers; Rodney McMullen, CEO of Kroger; Lori Lightfoot, former mayor of Chicago; and many more.

“I am happy that MIT Sloan is not just thinking about the future of work from a technical standpoint but is also shedding a light on communities that are often ignored,” says Wages.

“We have an outsized ability to influence so much,” adds Dart, “as my fellow MIT Sloan students are going to be in leadership positions one day.”

Visit the “Writing the Code: Second Chance Hiring” conference website to register to attend in person, or watch the livestream here.

For more info Andrew Husband Senior Writer & Editor, OER (617) 715-5933