Inside Slack’s bold bet on training formerly incarcerated people to be tech workers
When Jess Bonanno went to her office for the first time last October, at Salesforce’s 41-story high-rise in Midtown Manhattan, the experience was surreal. A year earlier, she had been a housepainter. Before that, in her early twenties, she had been in prison. Now, she’s a software engineer at Slack, the workplace messaging app that was acquired by Salesforce in 2021 in a $27.7 billion deal.
Bonanno was drawn to technology all her life. As a child, growing up in the 1980s, she used a computer to escape. “Just getting on it, I would lose myself,” she says. “I had a lot of reasons to escape then, even as a young child.” Her mother, who was addicted to heroin, died when Bonanno was eight. She didn’t know her father. She started getting into trouble, and eventually was incarcerated. When she was released, after having spent more than a year in prison in total, she took a job as a housepainter, which she kept for years, even though her boss routinely mistreated his workers. “I thought I couldn’t get a real career,” she says.
[Photo: courtesy Slack]
In 2019, while listening to the freeCodeCamp tech podcast, she heard a software engineer talking about the fact that he had also been incarcerated. A few months later, “I decided I was going to teach myself to code,” she says. She started going to a bootcamp at night after work. She joined Underdog Devs, a group of software engineers who volunteer to mentor aspiring developers who either had been incarcerated in the past or came from an economically disadvantaged background. Then she discovered Next Chapter, a nonprofit incubated at Slack that trains formerly incarcerated people, helping them get tech careers.
The program has trained 30 apprentices so far, including Bonanno, who has been promoted twice since she started at Slack less than a year ago. After their apprenticeships, all have been offered full-time jobs at tech companies—not only Slack but also Dropbox, Square, and Zoom.
“Learn to code” has become a horrible cliché, as if the act alone could magically elevate someone’s station in life. But it’s not about the power of technology so much as it’s about seeing the potential in every human being, no matter their prior circumstances. “When you think about reentry programs, they’re not normally high-level jobs or high-paying jobs,” says Deepti Rohatgi, a seven-year veteran of Slack and founder and executive director of Slack for Good, the company’s philanthropic arm. “They’re usually fairly junior—there’s janitorial, there’s gardening, there’s working in a restaurant. So what we do is very different than what we’ve seen other folks do.”
Rohatgi and her peers believe that after 4 years and its 30 successful placements, its program works. (Of course, 30 employees is still a tiny fraction of the workforce at Slack and its tech company partners; Slack alone has more than 2,500 employees.) Now, Slack wants to help more companies join the effort. Slack has partnered with 14 other businesses; Paypal, Asana, and Stash announced today that they are the latest to join. In a new joint initiative with the Aspen Institute, Slack is launching Rework Reentry, a project that aims to help the work scale by making it easier for other companies to do the same thing. The team will be producing a “tactical playbook,” which shares challenges that companies might face and strategies to overcome them. It also will organize events between tech leaders and justice-reform advocates, and will soon launch a series of short documentary films about what life is like after incarcerated people leave prison.
“There’s so many things we can and should be doing in the philanthropic space,” Rohatgi says. “But sometimes focusing on doing everything dilutes everything. So we’ve been laser-focused on our mission, and I think that laser focus has made it possible for us to move the needle because we have hundreds, now thousands, of employees focused on it. They understand what we’re trying to accomplish. And everybody is all in, right? Like, this is what we do.”
Starting late in President Obama’s second term, criminal justice reform seemed to be one of those rare issues that could win broad support. The powerful conservative Koch family and outspoken activists like artist John Legend found agreement that the United States shouldn’t be incarcerating as many citizens as it is—and it shouldn’t throw those people away after their prison terms. The “heart and mind change” necessary to propel this movement is facing new headwinds from a recent rise in violent crime, seen most acutely in Slack’s hometown of San Francisco, where reactionary forces—and self-inflicted political wounds—led to the ouster in June of the city’s reform-minded district attorney, elected just two years earlier. In this climate, Slack’s efforts appear even more bold, though the company’s leaders would never put it that way themselves. “It’s a wonderful way for our company and our employees to come together on a specific issue,” Rohatgi says, “and really see you can make systemic change.”
Chapter One
Next Chapter started in 2018, a few years after Slack CEO Stewart Butterfield had seen a talk by Bryan Stevenson, the public interest lawyer and author of Just Mercy, about his experience defending a man on death row who had been wrongfully accused. Butterfield was deeply moved. “At the time, at the end of 2015, Slack was on top of the world, the fastest company to [reach] $100 million in revenue,” he says. “We were worth a lot of money, and we had all this positive press, and we were growing really quickly. And people were really excited. I think, given the kind of extraordinary good fortune that we found ourselves in, it was especially important to remember the people who aren’t on top and the people who are suffering the most.”
The challenge of returning citizens had been on his mind for a while, since an earlier night when a man had approached him on the street in San Francisco saying that he had just gotten out of jail, had nowhere to go, no money, and nowhere to sleep. “That experience kind of stuck in my head—trying to imagine what that would be like, and how impossible it would be,” he says. Later, when he heard Stevenson’s story, he thought back to that experience and the practical challenges of reentry.
He handed out copies of Just Mercy to everyone at Slack with a note:
“It’s not really a happy book. In fact, it is the only book I’ve ever read that’s made me cry. But when you’re on top—especially when you’re on top—you should make sure to never lose sight of what it’s like to be on the bottom. I hope you find it as I did: moving, inspiring, bleak, anger-provoking, and ultimately hopeful.”
Later, executives at Slack visited San Quentin, where a program called The Last Mile was teaching a group of prisoners the basics of coding. “They were trying to learn without access to the internet,” Butterfield says. “That’s obviously very difficult and complicated. But they were also trying to learn how to develop software in an environment where many of them had been incarcerated since before the iPhone, before Facebook, before technology had made such a big impact in reshaping people’s lives. It’s hard even to comprehend the role that the technology plays.” Still, the Slack team was struck by the students they met. “Frankly, we were just blown away by the talent we saw,” says Rohatgi.
The Slack for Good team, which was formed in 2015 to focus on the mission of increasing the number of underrepresented people in the tech sector—and now is focused almost entirely on Next Chapter—started thinking about how it might be able to help address one of the many challenges of the justice system in the U.S.: When someone leaves prison, it’s incredibly difficult to find a job. At any given point, around 40% may be unemployed, and without work, they’re more likely to end up imprisoned again. The problem is huge because approximately 2 million Americans are incarcerated now, and almost all of them will eventually be released. “We thought about where we could move the needle and areas that we didn’t think anybody else would really want to engage,” Rohatgi says. They realized that there was a need not just for jobs, but for well-paying jobs.
In the first year after leaving prison, one 2018 analysis found that only 55% of employment-age men had any reported earnings; of those who did, the median earnings were around $10,000. “The primary driver of mass incarceration and recidivism is poverty,” says Ken Oliver, executive director of Checkr.org, the nonprofit arm of Checkr, a background-check company. “When people can’t access economic mobility jobs at $60,000, $70,000, $80,000 a year, then what happens is that they’re living in functional poverty in places like East Oakland, or the Tenderloin District in San Francisco, or South Central LA. They get locked out of the middle-class economy, so it’s very difficult for them to reskill or upskill.” More companies, he argues, should follow Slack’s example of training talent within their companies.
“Oftentimes, the people that we work with are part of a generational cycle of poverty, or an intergenerational cycle of incarceration,” says Kenyatta Leal, executive director of Next Chapter. A job through Next Chapter “helps break those cycles, but even more importantly, begin a cycle of potentially creating generational wealth. We’re already seeing apprentices from our first cohort . . . buying homes, starting families. They’re already teaching other family members how to get into software engineering as a career path.”
Next Chapter connects with potential apprentices through programs that teach programming in prisons or on reentry, including The Last Mile, Underdog Dev, and Emergent Works, although it’s also possible to join without prior training. When someone is accepted as an apprentice, they start with an intensive three-month bootcamp at Hack Reactor, considered one of the best bootcamps for developers. If they complete that successfully, then they’re placed with one of the program’s hiring partners, like Dropbox or Square, and embedded on an engineering team to work on real projects. Throughout the eight-month initiative, they’re paid—first a living stipend by Slack during the bootcamp, then a wage by the company in which they’re apprenticing—so they don’t have to worry about working a job on the side.
Apprentices also get support from a team as they proceed. A technical manager and director work with engineering teams at the host company so there’s a feedback loop if someone needs technical support. Staff from Next Chapter also help the apprentices adjust to office culture. “It is a big leap to go from prison to Slack or any of our other partners,” Rohatgi says. “There’s a lot of stuff that we all assume everybody knows—but they don’t.” (That includes, for example, what a 401(k) is, or stock options.) Apprentices also help each other figure out more quotidian challenges, like how to rent an apartment. An executive tech coach helps each apprentice set goals for their careers.
Companies hosting apprentices also have to prepare, beginning with an all-hands meeting at which Next Chapter and its partners—and sometimes guests like Bryan Stevenson or John Legend—talk about the issues that surround mass incarceration and why it’s important to give people second chances. Each manager who works with an apprentice has to go through additional training. “We don’t want to send an apprentice into a place that isn’t welcoming and not a place where they will thrive,” says Rohatgi.
Even within Slack, there was a little initial hesitance to be overcome. Shortly after some of the first visits to San Quentin, the company had invited someone who had recently been released from the prison to speak at the company. “It was really an interesting experience because I think it illustrated some of the depth and complexity of the issue,” Butterfield says. “Because we’re in San Francisco, obviously a pretty liberal, progressive place to begin with. And Slack is pretty liberal and progressive within that. There’s a lot of genuine interest in creating opportunities for people and stuff like that. But at the same time, people were like, ‘Okay, what did this guy do, if he’s gonna sit next to me? I want to know—I want to make sure that I personally feel safe.’ Which is a totally normal, and I think human, reaction.”
When Next Chapter first launched, Rohatgi says she heard from skeptics who said that it wouldn’t work: Other companies had previously tried to hire formerly incarcerated people into similar roles. But other apprenticeship programs often didn’t lead to full-time jobs for the participants. “Based on my conversations with people managing and participating in these other programs, this is because they did not build in cultural support systems, for either the individuals or their managers,” she says. “Our apprentices are very talented, but making the transition to corporate work in a tech company after years of incarceration is not always smooth. For programs like this to result in full-time offers and upward mobility, you have to go beyond getting individuals in the door and also invest in the technical and professional mentorship, and the peer and community support, that people need to thrive.”
It took a few years to set up the program, as the team had to work through some challenges—like the very real fact that some Slack customers have policies saying that workers with a criminal record can’t access their data. That meant that apprentices couldn’t work on some projects and had to start on a team that tests the quality of other engineers’ code work. Other companies that host apprentices are learning as they gain experience. Lynne Oldham, who first worked with apprentices as chief people officer at Zoom—and who is now bringing the program to her new role at the digital financial services company Stash—says that she thinks it would be helpful to host more apprentices at the same time, “so they have the ability to have a little more camaraderie and can look left and right and see someone like themselves,” she says. In the second year of the program at Zoom, the company timed it to begin with its college internship program so that everyone could attend some of the same introductory events. (Because of the pandemic, all of this was virtual.) But despite some minor challenges, Rohatgi says that Next Chapter has been a success. Of the three cohorts so far, only one person dropped out.
When De’Markus Matthews, now a developer at Slack, started as an apprentice, his first day was “nerve wracking,” he says. “But I felt a very warm welcome. I felt like I belonged there.” He says that he has felt a sense of imposter syndrome at times, but it helped to hear from mentors that others often feel the same way, regardless of whether they came from San Quentin or MIT. (In software, perhaps more than many other jobs, everyone has to continually learn new skills.) Bonanno, too, says that she’s always felt that she belonged. “I’ve always just been treated as another engineer,” she says. “That’s been the most helpful thing in helping me acclimate to this new life.”
The Next Mile
These jobs are not a fit for everyone leaving prison, says Checkr.org’s Oliver, who was previously incarcerated himself. “[Some] people exit prison after 15 or 20 years, and they’ve never seen a smartphone, they don’t know how to pay bills online on their phone, they have no idea about what Google Suite is, or Zoom, or any things that we take for granted every day. . . . I think it’s tough when you recognize that most people exiting prison in California’s average reading level is eighth grade,” he says. “But there are dozens of other tracks—project management, UX design, sales roles, human resources—that people can be trained in.” His organization is working on another program that will help train people for some of these other roles.
There are also likely tens of thousands of formerly incarcerated people who could be talented developers if given the chance. Part of the challenge is making people aware of what’s possible, says Matthews, who didn’t know anyone working in tech jobs when he grew up. He read an article about app developers in 2016 while in prison, and started thinking of apps he could develop himself; later, he had the chance to attend classes from The Last Mile before his release. When he went home, he didn’t have a computer, but kept training himself with books and on paper until he could attend a bootcamp. Now, “all my friends that I know that are formerly incarcerated, I try to talk them into it,” he says.
More training programs both in and out of prison, like The Last Mile and Emergent Works, can obviously help. More companies could also commit to helping train people who were incarcerated in the past. Fair-chance hiring has grown significantly over the last decade. Several companies, from Starbucks to Google, have voluntarily “banned the box”—removing checkboxes on job applications asking whether someone has a criminal record—and more joined in 2016 after a push from the Obama administration. Thirty-seven states, and the federal government, now ban the box for government job applications; 15 states also ban the box for private employers. After George Floyd’s death in 2020 led more companies to embrace diversity, equity, and inclusion programs, fair-chance hiring spread more widely. Over the past two years, the number of job postings on Indeed that include fair-chance employment has grown 31%. But programs like Next Chapter obviously go much further; and for a career in tech, that extra support may be necessary to get a job.
When someone just learns the basics of coding, “the missing component can be the social expectations and how to collaborate with people and what kind of communication is expected and how you work as part of a larger team,” says Butterfield. “If you don’t know how to speak to people, if you don’t know kind of what’s expected, if that’s all like a black box in the industry, that’s definitely something that people need to be trained in and supported in learning,” he says. An apprenticeship also helps teach someone how to code within an incredibly complex system, where any change in the code also impacts other parts of the system.
He acknowledges that an apprenticeship program takes resources. “You do need people who are there to support the program because there’s quite an investment in apprenticeship,” he says. “You also have to have the employees inside the organization who are really interested in this and willing to take on people as mentees and support them.”
Everyone involved in Next Chapter says making that investment is worth it. “The people coming home from these incarcerated settings—they’re people, you know, they’re not inmates, they’re not convicts, they’re not all of this pejorative language that we use to describe people who are leaving incarcerated settings,” says Leal. “They are people.” In a corporate context, they’re more than that, too. “We’re good engineers,” says Bonanno. “We’re good problem-solvers. I think of all the untapped talent out there; that’s a gift that the world is missing out on. We’re not bad people. We’ve made bad mistakes. Just imagine if every time you went to an interview, you had to talk about your most embarrassing moments—it would deter you from going on an interview in the first place.”
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