Jesse Aguirre’s workday at Slack starts with a standard engineering meeting—programmers call them “standups”—where he and his coworkers plan the day’s agenda. Around the circle stand graduates from Silicon Valley’s top companies and the nation’s top universities. Aguirre, who is 26, did not finish high school and has so far spent most of his adulthood in prison; Slack is his first full-time employer. But in the few years he has been writing code, he has cultivated what is perhaps the most useful skill in any software engineer’s arsenal: the ability to figure things out on his own.
Aguirre, along with Lino Ornelas and Charles Anderson, make up the inaugural cohort of Next Chapter, an initiative launched by Slack, in partnership with the Last Mile, the W.K. Kellogg Foundation, and Free America, to help formerly incarcerated individuals land jobs in tech. Last year, when Next Chapter launched as an apprenticeship program at Slack—but didn’t guarantee full-time employment—Alexis C. Madrigal wrote in this publication, “Offering an apprenticeship rather than a permanent job may not seem like a huge distinction, but multiple advocates for formerly incarcerated people called attention to this part of the program design.”
It was a fair point. Silicon Valley has often taken symbolic steps toward making the industry more equitable but has under-delivered on lasting change. In June, however, just days before Slack’s IPO, Aguirre, Ornelas, and Anderson were all offered full-time positions, complete with stock options. For Aguirre and his friends, this raised a new question: Could they make it? Access to an elite organization does not necessarily translate, of course, to success. “It’s true that nothing stops a bullet like a job,” Katherine Katcher, the executive director of Root & Rebound, a California-based reentry program, told me. “But reentry is complicated—a job alone without support is usually not enough.”
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