OpenAI has lost a second sales executive to Salesforce within a week.

      OpenAI's vice president of sales for the Americas has stepped down after just five months. Kaylin Voss is returning to Salesforce, as reported by The Information on Friday. Her departure followed just a week after her previous boss, Denise Dresser, who was OpenAI’s chief revenue officer and left after nine months.

      Both women previously worked at Salesforce, with Voss having served as Slack’s chief revenue officer before joining OpenAI. She had been implementing a plan that involved segmenting customers into various groups, such as telecommunications, retail, consumer goods, and manufacturing, focusing on cybersecurity, promoting adoption, and demonstrating a return on investment for businesses.

      Her former boss welcomed her return publicly, with Marc Benioff posting, “Welcome Home to The Ohana @KaylinVoss!” on X, linking to the news of her departure. This post received over 135,000 views. Amir Efrati from The Information succinctly remarked, “Kaylin is going back to… Salesforce.”

      OpenAI introduced Dali Rajic as its new chief revenue officer in mid-August, replacing Dresser. As reported by Emily Forlini for Fortune, this marks the company’s fifth C-suite change in just a year. Rajic, 53, previously held positions as president and chief operating officer at Wiz, the cybersecurity firm acquired by Google for $32 billion this year. He will commence his role this week.

      According to CNBC, OpenAI investor Josh Kushner introduced Rajic to the company, and Greg Brockman made the appointment, as per a source who spoke with Fortune. Brockman took over the revenue organization in early July after Fidji Simo resigned from her position to concentrate on her health.

      Rajic had a successful tenure at AppDynamics, starting in sales in 2012 and ultimately becoming chief revenue officer, assisting in the company’s pitch to investors before its acquisition by Cisco for $3.7 billion right before its planned market debut. He also spent five years at Zscaler as president of go-to-market before moving to Wiz in 2024. Jyoti Bansal, co-founder of AppDynamics, noted that if OpenAI needs to catch up in enterprise, Rajic is the right choice. Fortune reported that a source connected to Anthropic considered his recruitment a significant win.

      Rajic has a decade of experience in selling security software, which is pivotal as OpenAI aims to enhance its security offerings. The company promotes its models to help businesses thwart hacks and breaches through a program called Daybreak, which was expanded into various access tiers on August 10.

      Colleagues have mentioned that Rajic approaches sales as a science rather than an art. Although he did not comment on that article, he validated the details within it. He employs the MEDDPICC framework, which assesses deals based on several criteria, including metrics, the economic buyer, and competitive landscape. This methodology also forecasts the potential success of sales personnel shortly after they start by tracking initial meetings arranged and demos conducted. A former colleague emphasized the importance of efficiency, stating that those who do not meet expectations are promptly reassigned.

      Rajic learned his sales approach from John McMahon, referred to as the godfather of enterprise sales, while at BMC Software in the early 2010s. Shardul Shah, a partner at Index Ventures, referred to the alumni network that emerged from PTC as the “PTC Mafia,” likening it to the PayPal Mafia, which includes notable leaders from MongoDB and Datadog.

      Originally from Yugoslavia, Rajic relocated to Germany at age one and moved to the United States at 16. He earned a degree from Cal Poly Pomona and an MBA from Northwestern. Colleagues portray him as straightforward, intellectual, and tenacious, with one recalling him as "the Croatian Sensation" after witnessing him grab two hard-boiled eggs from Starbucks on his way to a meeting.

      In social settings, he tends to be reserved and does not actively seek speaking opportunities or engage on X.

      Dresser managed a commercial team of about 1,200 people, traveling to meet clients and working through weekends while advocating for detailed reporting that the company lacked. Both current and former staff have noted the significant changes within the organization over the past few years, expressing that keeping up with the pace has been challenging.

      OpenAI recognizes the frequency of leadership transitions as typical for a rapidly growing company. They appointed Rajic to guide the next growth phase and mentioned having a strong group of senior leaders in place. Dresser has not responded to requests for comment from Fortune.

      Currently, enterprise revenues now surpass those from consumers for OpenAI, a goal achieved ahead of expectations, as reported by CNBC. The organization seeks to capture market share currently held by Anthropic, whose revenues exceeded OpenAI's for the first time last quarter. Anthropic is also preparing for a potential IPO that could rival SpaceX’s record, possibly filing as soon as next month