In the last two weeks of August 2026, two of the operators OpenAI had hired to build its enterprise sales organization quit and went back to Salesforce.
The first was Kaylin Voss. At Salesforce she had spent nearly eight years and risen to executive vice president of Agentforce and Data Cloud, the two products at the center of Salesforce's entire artificial-intelligence strategy (LinkedIn, 2026). In April 2026 she left that seat to run OpenAI's sales across the Americas. Around August 21 she resigned and went back, roughly five months later (The Information, 2026; The Next Web, 2026). Marc Benioff welcomed her in public, calling it a return "home to the ohana" (Salesforce Ben, 2026).
Within the same stretch, Peter Doolan followed her out the same door. Doolan had been the chief customer officer of Slack; at OpenAI he ran artificial-intelligence transformation for the go-to-market organization; he too returned to Salesforce (The Information, 2026; Salesforce Ben, 2026).
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No CRO gets fired for missing a forecast. They get fired for missing three in a row.
Issue 10 publishes on schedule. The corpus keeps reading while you sleep.
Run the diagnostic