Stewart Butterfield got one hour with Marc Benioff before Salesforce's $27.7B Slack deal, early Slack builder writes
What's the story? Stewart ButterfieldDealroom has a profile for this one. Try Dealroom → had only about an hour of face time with Salesforce founder Marc Benioff before Salesforce announced its $27.7 billion acquisition of Slack. "My last meeting with him was cut short because McConaughey arrived," Butterfield told Johnny Rodgers, who spent 11 years building Slack, for the latest instalment of Rodgers' Building Slack series, published on 23 October 2026. Actor Matthew McConaughey is a paid Salesforce spokesperson.
Culture clash Rodgers describes a 4,000-person company being absorbed by an 80,000-person one: help requests that went from a Slack channel to a ticket and an automated email, mandatory Trailhead quizzes, internal email again, and Salesforce sales reps who found Slack hard to sell because it did not fit the vertical, single-buyer products they knew. Butterfield, he writes, was frustrated by what he saw as operational inefficiency, from expensive celebrity appearances alongside cuts to staff travel to waves of over-hiring and layoffs, and his feedback to Benioff and then co-CEO Bret Taylor went largely unheeded.
The exit The tipping point came at Davos: expecting to meet customers, Butterfield found himself booked on an innovation panel with will.i.am, another Salesforce celebrity spokesperson. He planned to announce his departure on 1 December 2022, with Salesforce's Lidiane Jones succeeding him. The day before, Taylor abruptly announced his own exit. "I had no idea," Butterfield posted. "The problem has been, there's no incorporation of the Slack culture into the Salesforce culture," he had told staff at an all-hands. "It's just elimination."
Context Huddles and Clips, built in-house during the pandemic, shipped in mid-2021 as Slack's first major features under Salesforce. Rodgers says one more Building Slack post is still to come. He is now building Supergroup.
Sources: Building Slack: Salesforce, Part Two · Johnny Rodgers on X · Sheel Mohnot on X
