The biggest surprise about today’s news that Slack co-founder Stewart Butterfield is departing Salesforce, nearly 18 months after the company acquired Slack, may be that he was still there! It’s not unusual for founders of multibillion-dollar companies like Slack to exit shortly after their firm is acquired. Even so, coming a few days after Salesforce’s co-CEO Bret Taylor quit, Butterfield’s exit can only reinforce the image of a company that has a hard time holding onto entrepreneurial talent. (Butterfield told colleagues the timing was coincidental.) Salesforce stock, which fell last week on the Taylor news, dropped another 7% today to its lowest point since early April 2020.

Where does this story go from here? Put it this way: It’s a combustible situation. In October, Bloomberg reported that activist investor Starboard Value had surfaced as a shareholder in Salesforce. CEO Marc Benioff only has a 2.8% stake in Salesforce, according to securities filings, so the company is vulnerable to outside pressure. Starboard, which loves to terrorize tech firms, reportedly wanted to push the company to focus on improving its profit margins. That’s reasonable, given Salesforce’s profit track record. In the October quarter, for instance, Salesforce reported operating income of $460 million on revenue of $7.8 billion, a meager margin of 5.9%. And that was a big improvement on the second quarter! In contrast, Microsoft had an operating profit margin of 43% in its most recent quarter, while Oracle’s was 23%.