Even before starting at Slack, there was the not-insignificant challenge of relocating to Silicon Valley—which Aguirre, Ornelas, and Anderson all had to do in order to accept their positions. All three had been paroled into other jurisdictions. Not only does transferring one’s parole assignment require a long, bureaucratic process, but simply finding an affordable place to live that accepts people with a criminal record—especially in the Bay Area, with its tight housing market—can be a full-time job in itself. Aguirre said he was pressured to leave the first place he lived by a roommate who grew uncomfortable with the idea of living with someone who had been in prison. After staying with a friend for almost a year, he applied for more than 50 apartments before he was able to find a more permanent home.

“Finding a job is one thing—we all know the stigma associated with incarceration makes it really difficult to find work—but the same exists for housing,” said Kenyatta Leal, who is formerly incarcerated himself and now works for Slack as the “reentry manager” for the Next Chapter program.

Read: How Slack got ahead in diversity

Leal serves as a player-coach, mentoring Aguirre, Ornelas, and Anderson through issues such as housing, financial literacy, workplace norms, and the multitude of other reentry challenges that he has overcome himself. In addition to working with Leal, Aguirre, Ornelas, and Anderson also each have a technical mentor, a work-culture mentor, and a career coach, and Slack’s nonprofit partners help the apprentices navigate housing, parole, and travel, and educate Slack’s employees on criminal-justice issues. All of this helped Aguirre feel more welcome at the office, despite having come from a different background than those of many of his colleagues.

Aguirre grew up in Lynwood, California, a predominantly Latino community in South Los Angeles. When he was 11, his family moved east to Orange County, and a couple of years later Aguirre became involved with members of a local gang. He was cited by the local police for some minor offenses, like tagging a telephone pole in chalk, but no serious charges resulted.

Then, on March 13, 2010, Ramon Magana, a young man with local gang affiliations, was shot with a shotgun carrying bird-shot ammunition. Witnesses at the scene said that Aguirre was not the shooter, but, according to police testimony, he had handed the gun to the person who eventually committed the crime. Aguirre was charged as an adult with attempted murder, assault, and gang affiliation. A few weeks after he turned 18, he was shipped off to prison with a life sentence.

Aguirre’s sentence spurred a public outcry. In 2014, a California Court of Appeal determined that Aguirre had “ineffective” counsel and that his sentencing “raised issues of cruel and unusual punishment.” In a resentencing hearing, his time was reduced to seven years, plus a state-mandated 10-year enhancement for gang-related activity. Then, on Christmas Eve 2017, Aguirre learned that Jerry Brown, then the governor of California, had decided to cancel the 10-year enhancement, citing Aguirre’s exemplary behavior and work ethic in prison. By that time, Aguirre had gotten his GED, completed the coding boot camp, and served nearly eight years behind bars. He was up for immediate release.

The prior year, Slack CEO Stewart Butterfield and a group of co-workers had visited a Last Mile program at San Quentin State Prison, just north of San Francisco. Butterfield was particularly impressed by the program’s rigor and the quality of the software the inmates were producing. Around the time Aguirre was released, Slack started laying the groundwork for what would eventually become Next Chapter.