In mid-August, OpenAI announced a new chief revenue officer—its fifth C-suite shakeup in the past year, but arguably its most important as the company sprints toward what could be an historic IPO, likely in 2027.
The company said that Dali Rajic, the president and COO at Google-owned cybersecurity company Wiz, would replace Denise Dresser as CRO. Dresser held the role for less than a year, leaving many to wonder what happened, and why OpenAI chose Rajic.
Rajic, 53, has earned a reputation as one of the most disciplined, successful enterprise sales leaders in tech. OpenAI being able to recruit him was a “coup,” one source with ties to OpenAI rival Anthropic tells Fortune. OpenAI now has more revenue from enterprises than consumers, a milestone it hit earlier than planned, CNBC reports. The team is working aggressively to capture market share from Anthropic, which is reportedly planning to IPO as soon as September, meaning it will likely beat OpenAI to the public markets.
“If OpenAI is behind on enterprise, he is definitely the guy,” says Jyoti Bansal, who hired Rajic in 2012 to lead sales for AppDynamics, the application performance management platform Bansal cofounded and ran. Rajic then worked his way up to become CRO, and was a key part of the team pitching AppDynamics to investors for a possible IPO. The company almost went public in March 2017 before Cisco swooped in the day before the planned market debut and purchased it for $3.7 billion.
The Cisco deal required Rajic to stay for two years, and then in 2019 he joined enterprise cloud security company Zscaler as the president of go-to-market and CRO. In 2024, he moved to another enterprise cybersecurity company, Wiz, which Google acquired in 2026 for a whopping $32 billion, its largest acquisition to date.
Rajic’s cybersecurity background is of particular interest to OpenAI. The company is looking to significantly grow its revenue in this area, pitching businesses on using its models to prevent hacks and breaches. OpenAI calls its flagship cybersecurity program Daybreak, and it expanded into multiple access tiers on August 10.
Intense, well-dressed, and a fan of Starbucks hard-boiled eggs
Rajic is disciplined, blunt, and intellectual, according to four people who have worked with him previously, two of whom requested anonymity to speak freely about the increasingly influential Silicon Valley figure. Rajic declined to comment for this piece, but confirmed the accuracy of the details included here.
Rajic was born in Yugoslavia, in an area which is now Croatia, and moved to Germany when he was one year old. Growing up, he always dreamed of coming to America, and moved to the U.S. at age 16 for his last years of high school, he said on a 2022 episode of the Grit podcast. He then attended California State Polytechnic University, Pomona for undergrad, followed by an MBA from Northwestern University’s Kellogg School of Management.
“He is one of the most intense people you will ever meet,” one former friend and colleague of Rajic’s tells Fortune. “We would call him the Croatian Sensation. I remember we would get breakfast, and his version of breakfast was on our way to a meeting would grab two hard-boiled eggs at Starbucks, stuff them in his mouth, and be like, ‘That’s breakfast. Let’s go.’”
At a party, he is more often in a quiet place engaging in deep discussion with one or two people—not working the room, those who know him say. He “doesn’t like to talk about himself,” one friend said. Though he’s well-dressed and disciplined with his health, he’s not quick to get in front of a crowd and accept public speaking gigs. Unlike many prominent executives who take to social media these days to espouse their hot takes, Rajic doesn’t have an X account at all.
OpenAI’s salesforce buffeted by change, leadership turnover
Rajic’s predecessor, Dresser, also approached her work with notable intensity. One former employee who worked under her said she pushed hard for organizational change, such as trying to set up reliable, granular reporting. She worked around the clock, sometimes calling a colleague late at night on weekends for a long chat. Dresser herself was “always on the road,” a source said, meeting with prospective clients “almost like the most senior salesperson” within the roughly 1,200-person commercial organization she oversaw. Rajic will also be on the road frequently, as travel is a key part of the job, OpenAI said.
Current and former employees within the organization Rajic is taking on say they have experienced constant change over the past few years, and it is exhausting to keep up with.
Dresser’s departure has led to more turnover. Kaylin Voss, OpenAI’s VP of Americas, is leaving to return to Salesforce, The Information reports, where she previously worked with Dresser. She joined OpenAI five months ago. Voss spoke with Fortune a month ago, where she explained her team’s strategy of segmenting businesses into groups, such as telecommunications, retail, consumer goods, and manufacturing. Cybersecurity was a big focus, as well as driving adoption and clarifying ROI.
OpenAI acknowledges the high number of leadership changes, and says it’s similar to other fast-growing companies. In Rajic’s case, he was selected to lead the next phase of growth for the revenue organization, and the company is confident in its strong bench of senior leaders across the organization, an OpenAI spokesperson said.
Dresser did not respond to requests to comment for this story. OpenAI investor Josh Kushner introduced Rajic to OpenAI, CNBC reports. OpenAI co-founder and president Greg Brockman then decided to hire him, according to a source familiar with the decision. Brockman took over the revenue organization in early July after CEO of Applications Fidji Simo departed to focus on her health.
A fresh sales philosophy, but how long will Radic last?
Rajic approaches sales as primarily a science, not an art, his former colleagues say. He’s a disciple of the MEDDPICC philosophy for enterprise sales, created in 1996 at the Boston-based company PTC by Dick Dunkel, Jack Napoli, and John McMahon. Rajic is the “protege of John McMahon, the godfather of enterprise sales,” a source says. Rajic worked with McMahon at BMC Software in the early 2010s.
MEDDPICC is a sales framework and training program. The acronym stands for: Metrics, Economic Buyer, Decision Criteria, Decision Process, Paper Process, Identify Pain, Champion, Competition. These eight parts of the sales process aim to help organizations evaluate the viability of prospective deals and forecast revenue.
“I’m sure you’ve heard of the PayPal mafia,” said Shardul Shah, a partner at Index Ventures who has known Rajic for years. “In the world of go-to-market, the equivalent is the PTC Mafia.” Multiple top tech executives come from this sales tradition, such as Dev Ittycheria, the CEO of MongoDB, Cedric Pesh, MongoDB’s CRO, Dan Fougere, the CRO of Datadog—and Dali Rajic.
Another key part of the philosophy is using “leading indicators” to predict which sales people will be successful within just a few months of them starting the role. This includes tracking how many first meetings someone has set up, and how many customer demos they’ve done, among other metrics.
For those that aren’t making the cut, “you don’t hesitate, you move them out of the business,” one of Rajic’s former colleagues tells Fortune. The end goal is creating a “very disciplined, highly predictable, scalable go-to-market machine,” the person said.
This type of predictable revenue is exactly what investors will be looking for leading up to OpenAI’s IPO, the source said.
Rajic starts this week, and plans to spend a significant amount of time traveling to clients and in San Francisco, possibly living there part time, his friends say. He currently lives in Austin, Texas, with his wife and three kids. He is excited and eager to get going, according to his friends. But how long will he last?
“It’ll be interesting to see if Dali is there in 12 or 18 months, or if he will burn out like so many other people do at OpenAI,” one source tells Fortune. “That’s the open question.”
This story was originally featured on Fortune.com
