HireAug 26, 2026, 18:35 UTC

OpenAI loses second Salesforce sales exec as 22 more weigh return

What's the deal? Peter Doolan, a senior OpenAI sales executive, has signed an offer to return to Salesforce, according to a person with direct knowledge of the matter. He is the second such departure in a week, following Kaylin Voss, who led OpenAI's sales for the Americas.

The reshuffle: Doolan will become Salesforce's chief customer officer for a new AI labs initiative that sells products from the company's acquisitions. Voss joins as executive vice president of sales for the team. Salesforce bought supply chain automation startup Regrello in 2025 and in June said it would acquire AI customer support startup Fin.

Why now? The exits follow OpenAI's move earlier this month to hire Dali Rajic, president and chief operating officer of Alphabet-owned cybersecurity firm Wiz, as its new chief revenue officer. He replaces Denise Dresser, who had recruited Doolan, Voss, and other Salesforce staff to build OpenAI's enterprise sales team.

Scale of the shift: Another 22 former Salesforce employees now at OpenAI are in active talks to return, the person said. Doolan, who was OpenAI's global head of AI transformation, spent 10 years at Salesforce before serving as chief customer officer of its messaging app, Slack.

What's the endgame? Dresser had tripled the size of OpenAI's sales team as the company pushed beyond its consumer chatbot to catch Anthropic's lead in selling AI to businesses. Enterprise sales accelerated after OpenAI released GPT-5.6 in July, according to a person familiar with the matter.

The signal: The talent is flowing both ways between OpenAI and Salesforce, and a leadership change at the top is unwinding the enterprise team Dresser built. How many of the 22 follow Doolan and Voss will show whether this is a trickle or an exodus.