Here is an excerpt from this week’s newsletter. To get the full newsletter to your inbox on Tuesdays, click here.

Now that we’ve learned Stewart Butterfield is stepping down as CEO of Slack in January, there’s much debate as to why. I take him at his word that this was a planned exit. He gave us plenty of warning. Early in the pandemic, as some of us were crouched over computers in our living rooms, paranoid that some zombie child would wander by half-dressed during a video call, the cofounder and CEO of the popular messaging app moved to Colorado and got in 76 days of skiing that season.

Not that he was slacking off, mind you. “A lot of those skiing days, just to be clear, were like 73 minutes before meetings started for the day,” he recently told my colleague, Jena McGregor, sounding wistful that an anecdote intended to illustrate the joys of remote work had instead reminded some of us that it’s good to be rich.

At the time, he certainly had reason to celebrate. In December 2020, Salesforce agreed to acquire Slack for $27.7 billion, a deal that Salesforce CEO Marc Benioff dubbed “a match made in heaven.” Butterfield married longtime girlfriend Jen Rubio, cofounder of Away Luggage, where I recently bought this lovely Vaquera carry-on and accidentally gifted it to myself. They moved to a six-bedroom house in Aspen and had a baby.


Fast-forward two years and Butterfield has become a pundit on all matters related to the world of work. (We recently named him to our Future of Work 50 list) Sure, anyone making collaboration tools is motivated to help us connect from all parts of the planet. But, as befits a man with a philosophy masters from Cambridge, Butterfield has also led the charge in reimagining how we work—from fewer meetings to more focus on incentivizing positive behaviors. As he told Jena: “People are making tweets or blog posts or articles that are speculating about what’s going to happen to them, as opposed to them being actors in creating it.”

Some link Butterfield’s departure to the announcement that Salesforce co-CEO Bret Taylor is also stepping down in January. While Butterfield wrote that he was sad to hear of Taylor’s departure, he subsequently wrote that it was simply a coincidence as he’d been planning to step down for months. I believe him. Founders and CEOs often leave within two years of an acquisition; it’s typically laid out as a condition of the deal. (Slack’s new CEO Lidiane Jones already has her new banner up. You go girl!)

But others are leaving, too. Slack veterans Tamar Yehoshua and Jonathan Prince are leavin; Tableau CEO Mark Nelson also quit in recent days. (Adam Selipsky was CEO of the data visualization software company when Salesforce acquired it in 2019, leaving in 2021 to run Amazon Web Services.) Another impending departure: President and chief strategy officer Gavin Patterson.

Is it a shakeup? The economy? A consequence of Starboard Value CEO Jeff Smith recently coming on as an activist investor? (To see Smith’s presentation, start on slide 15.) Salesforce recently reported a 14% year-over-year increase in third-quarter revenues to $7.84 Billion with earnings of $210 million, less than half the total a year earlier. That’s a far cry from the 20-30% growth that investors are used to seeing. It means there’s hard work ahead.

Being an entrepreneur is hard work—but it’s often a different kind of hard work than what’s needed to turn around a large company in a tough economy. Serial entrepreneurs like Butterfield are often itching to start a new gig once there’s a layer above them. Co-CEO Taylor said he wanted to “return to his entrepreneurial roots” when announcing his departure. (Being co-CEO of Salesforce while chairing the Twitter board—until recently—wasn’t enough excitement for him?)

Butterfield, meanwhile, is reportedly fantasizing about gardening. Perhaps Butterfield wants time to think. He did, after all, grow up in a commune in rural British Columbia before pursuing a philosophy degree and founding two successful startups (Flickr and Slack). As a fellow Canadian, I say, let my people garden. Maybe he will meditate on a future of work that’s measured by a different bottom line.


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