Stewart Butterfield spent barely an hour in total face-to-face meetings with Marc Benioff before

Stewart Butterfield Spent One Hour with Marc Benioff Before the Salesforce Deal

Stewart Butterfield spent barely an hour in total face-to-face meetings with Marc Benioff before Salesforce agreed to acquire Slack for $27.7 billion in December 2020, according to an account published by Johnny Rodgers, one of Slack’s original eight team members and a former principal engineer who spent 11 years at the company. Butterfield’s final meeting with the Salesforce chief executive was cut short because Matthew McConaughey arrived at the office. The transaction valued Slack at $45 a share, more than double its trading price at the time.

The Tech TL;DR:
• Slack co-founder Stewart Butterfield had approximately one hour of total facetime with Marc Benioff before the $27.7 billion acquisition agreement was finalized in late 2020.
• Post-acquisition integration frictions included executive spending on celebrity appearances, mandatory Trailhead quizzes, and sales teams defaulting to legacy vertical products over Slack.
• Butterfield ultimately decided to leave the company in late 2022 following a Davos panel assignment alongside will.i.am, occurring just before Bret Taylor announced his own departure.

Salesforce Culture Clashes with Slack Leadership

The buyout brought two distinct enterprise software cultures under a single corporate umbrella following the deal’s close in July 2021. Bret Taylor, then Salesforce’s chief operating officer, had approached Slack in the late summer of 2020 as the platform neared $1 billion in annual recurring revenue. While Salesforce praised Slack Huddles—the quick audio call feature launched in mid-2021—internal realities proved starkly different. According to Rodgers’ account, Butterfield found executive inefficiencies baffling, noting instances where leadership approved expensive celebrity appearances while cutting employee travel between offices and funding expensive annual senior staff retreats to Hawaii.

Cal Henderson, Slack’s co-founder and former chief technology officer, explained to Rodgers that Salesforce’s sales apparatus struggled to adopt the product. Because Salesforce traditionally sells into one department at a time rather than requiring broad leadership buy-in, sales teams defaulted to familiar vertical software they understood. Rodgers noted that Benioff himself did not use Slack and did not fully grasp the tool, despite publicly endorsing its capabilities during company all-hands meetings.

The Davos Panel and the Exit of Slack Leadership

Operational frictions accumulated over the first two years inside Salesforce, culminating in Stewart Butterfield’s departure in the autumn of 2022. The breaking point occurred during a trip to Davos where Butterfield expected to meet enterprise customers. Instead, organizers booked him on an innovation panel alongside will.i.am, a celebrity spokesperson for Salesforce. Butterfield described the situation bluntly in an internal communication reported by Fortune at the time, stating that without the incorporation of Slack culture, the acquisition amounted to elimination rather than integration.

Butterfield planned to announce his resignation for December 1, 2022, with Salesforce executive Lidiane Jones designated to take over the CEO role. A day before that planned announcement, Bret Taylor—who had brokered the acquisition—announced his own departure from Salesforce, a move that caught Butterfield entirely by surprise. Johnny Rodgers remained with the organization until the spring of 2023 before departing to build a new communication platform called Supergroup.