OpenAI loses a second sales leader in a week to Salesforce
Kaylin Voss, OpenAI’s vice-president of sales in the Americas, has resigned after five months and is returning to Salesforce, according to The Information. She is the second sales executive to leave within a week, with the new chief revenue officer starting this week.
August 24, 2026 – 6:47 pm
Guildford, UK – February 10, 2024: Hand holding a smartphone in front of OpenAI logo on white screen in background.
Credit: Henry Franklin via Shutterstock
OpenAI’s vice-president of sales in the Americas has stepped down after just five months in the role. Kaylin Voss is returning to Salesforce, as reported by The Information on Friday.
She left a week after her former boss, Denise Dresser, OpenAI’s chief revenue officer, walked out after nine months. Both women joined OpenAI from Salesforce. Voss had previously been Slack’s chief revenue officer.
Voss had shared her sales strategy with Fortune a month prior to her departure, outlining plans to segment customers into groups and focus on cybersecurity, along with driving adoption and demonstrating ROI. Her former boss welcomed her back publicly:
"Welcome Home to The Ohana @KaylinVoss!" Marc Benioff posted on X, linking to the story about her departure. The post has been seen over 135,000 times.
Amir Efrati of The Information succinctly summarized, "Kaylin is going back to… Salesforce."
OpenAI named Dali Rajic as chief revenue officer mid-August, replacing Dresser. It marks the company’s fifth C-suite change in a year, as reported by Fortune.
Rajic, 53, was previously president and COO at Wiz, the cybersecurity company acquired by Google for $32bn this year. He begins his new role this week, introduced to OpenAI by investor Josh Kushner, according to CNBC. The hiring was confirmed by a source reached by Fortune.
Why OpenAI sought Rajic:
"If OpenAI is behind on enterprise, he is definitely the guy," said Jyoti Bansal, co-founder of AppDynamics who initially hired him.
A source with connections to Anthropic characterized the recruitment as a coup for OpenAI.
Cybersecurity Focus:
Rajic’s decade of selling security software aligns with OpenAI’s efforts to promote its models for hack prevention and breach mitigation through the Daybreak program, which expanded access tiers on August 10th.
His Sales Approach:
Rajic treats sales as a science, relying on the MEDDPICC framework—a deal-scoring method built at PTC in 1996—which assesses deals based on metrics, economic buyer, decision criteria, decision process, paper process, identified pain points, champion, and competition. He predicts successful salespeople within months of joining using booked first meetings and demo runs.
"You don’t hesitate, you move them out of the business," a former colleague remarked about those who fail to meet expectations.