OpenAI has experienced the departure of its second sales leader within a week, as they move to Salesforce.

      OpenAI's vice president of sales for the Americas has stepped down after just five months in her position. According to The Information, which reported the news on Friday, Kaylin Voss is returning to Salesforce. Her resignation came one week after Denise Dresser, OpenAI's chief revenue officer, left after nine months in the role. Both Voss and Dresser previously worked at Salesforce, with Voss serving as Slack's chief revenue officer before her arrival at OpenAI.

      Voss had been developing a plan that involved segmenting customers into various categories, including telecommunications, retail, consumer goods, and manufacturing, with a particular focus on cybersecurity and promoting adoption while demonstrating a return on investment.

      Marc Benioff publicly welcomed Voss back on X, saying, “Welcome Home to The Ohana @KaylinVoss!” with a link to the article about her departure. The post has garnered over 135,000 views. Amir Efrati from The Information succinctly summed up her return with the words, “Kaylin is going back to… Salesforce."

      OpenAI has appointed Dali Rajic as the new chief revenue officer, starting this week, following Dresser’s departure in mid-August. This marks the fifth change in OpenAI's executive team within a year, as reported by Emily Forlini for Fortune. Rajic, 53, previously served as president and chief operating officer at Wiz, a cybersecurity firm acquired by Google this year for $32 billion. He was introduced to OpenAI by investor Josh Kushner, with Greg Brockman making the hiring decision after taking control of the revenue organization in early July.

      Rajic has a background in sales, previously leading the sales team at AppDynamics and helping to facilitate its acquisition by Cisco for $3.7 billion just before its planned market debut. He later spent five years at Zscaler and moved to Wiz in 2024. Jyoti Bansal, co-founder of AppDynamics, noted that if OpenAI is aiming to strengthen its enterprise efforts, Rajic is the right choice. A source linked to Anthropic called Rajic's hiring a significant achievement, according to Fortune.

      Rajic has spent the last decade selling security software, which aligns with OpenAI's goal to significantly increase its sales in this area. The company is promoting its models to help businesses mitigate hacks and breaches through a program named Daybreak, which was expanded into multiple access tiers on August 10.

      Former colleagues describe Rajic's sales approach as systematic rather than artistic. While he did not comment on a Fortune article highlighting his methods, he confirmed its accuracy. He adheres to the MEDDPICC framework, which evaluates deals based on various criteria and metrics, predicting potential success based on early sales activities. A former colleague emphasized a rigorous approach to performance, stating that those who fail to meet expectations are quickly removed.

      Rajic’s sales philosophy, learned from John McMahon at BMC Software, emphasizes a disciplined and predictable go-to-market strategy. This predictability is crucial for attracting investor interest ahead of a public listing. Shardul Shah from Index Ventures likens Rajic's alumni network to the "PTC Mafia," drawing a comparison to the well-known PayPal network.

      Rajic was born in what is now Croatia, moved to Germany at one year old, and came to the U.S. at age 16. He studied at Cal Poly Pomona and earned an MBA from Northwestern. Colleagues describe him as straightforward, intelligent, and tenacious. He is known for his straightforward demeanor but tends to avoid networking at events and does not have a presence on X.

      Rajic takes over a commercial organization of approximately 1,200 employees, which Dresser managed while meeting clients personally and pushing for detailed reporting. Current and former staff members describe the recent years as marked by continuous change and the challenge of keeping pace. OpenAI has acknowledged the frequent leadership transitions as normal for a rapidly growing organization and has expressed confidence in Rajic's ability to lead its next growth phase, supported by a robust team of senior leaders. Dresser did not respond to requests for comments from Fortune.

      Currently, OpenAI earns more revenue from enterprise clients than from consumers, reaching this milestone ahead of schedule, as reported by CNBC. The company is in competition for market share with Anthropic, which has surpassed OpenAI in revenue for the first time last quarter and is preparing for a potential listing that could rival SpaceX's achievements, potentially filing as early as next month. OpenAI's chief financial officer indicated the company plans to go public in 2027 or sooner, suggesting that its primary competitor could reach that goal first.

      While Rajic resides in Austin with his wife and three children and anticipates spending significant time in San Francisco, there remains uncertainty regarding his long-term position at OpenAI. A source mentioned the open question of whether he will last the typical tenure at the company, which has seen many employees become overwhelmed.

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