The Atlantic

Big Tech's Newest Experiment in Criminal-Justice Reform

The unicorn start-up Slack is launching an apprenticeship program for formerly incarcerated people. But will the industry ever hire from the inside en masse?
Source: Robert Galbraith / Reuters

On the fifth floor of Slack’s new building, overlooking the fancy Salesforce Park, a standing-room-only crowd of employees had gathered. Almost universally young and San Francisco casual, but not universally white and male, they were there to see John Legend, and to celebrate Next Chapter, a new partnership the chat start-up has entered into with The Last Mile, a technology-training program for incarcerated people, and $800,000 from the W. K. Kellogg Foundation.

Next Chapter will train and place three “returning citizens” inside Slack as quality-engineering apprentices—and build a process to help them acculturate to one of the most successful start-ups of the past decade, with help from a small support team led by a formerly incarcerated man named Kenyatta Leal. The apprenticeship is split into three parts over a year: Roughly four months at the start-up bootcamp Hack Reactor, four months of training, and then four months on the job, after which Slack may hire an apprentice, or help them get a job at another tech company. Everyone involved with the program seems to believe that if they can make the proof of concept work at Slack, other companies in technology and far beyond might also begin to hire more men and women who’ve paid their debts to society.

The Slack staff knew about this effort, and whether it was the program, the celebrities, or it being a Thursday afternoon—the slot in the week when Slack hosts “gather hour,” its more inclusive, less drunk spin on happy hour—the room felt like a high-school auditorium before a pep rally. The celebrities appeared and a raucous wave of applause overtook the crowd as Legend, Leal, the comedian Robin Thede, and Slack’s CEO, Stewart Butterfield, took the stage.

Butterfield is small. If you’re used to Elon Musk’s bombast, Mark Zuckerberg’s cheery will to power, or even garden-variety start-up boosterism, Butterfield is refreshing and strange, having retained some of that ’90s internet funk. He is the kombucha of tech CEOs.

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