Five years ago, Salesforce paid $750 million to buy a startup called Quip that made an internet-based word processor and spreadsheet app meant to give Microsoft’s competing Office products a run for their money. That didn’t happen, but Salesforce did get a valuable asset out of the deal: Bret Taylor, Quip’s founder, who has risen to become the No. 2 executive at Salesforce.

Now Taylor has the job of making sure the biggest deal in Salesforce’s history—its nearly $28 billion acquisition of Slack Technologies, which closed last week—works out better than its purchase of his startup did. Like Quip, Slack faces the formidable task of competing with a product from Microsoft, one of the most entrenched and powerful companies in enterprise software. While Slack has complained to regulators that Microsoft isn’t playing fair in the market, even some fans of Slack’s quirky messaging tool say innovation has stagnated at the company.

Read the full article at The Information!