OpenAI loses a second sales leader in a week to Salesforce

OpenAI’s vice-president of sales in the Americas has resigned after five months in the job. Kaylin Voss is going back to Salesforce, according to The Information, which broke the story on Friday.

She left a week after her former boss. Denise Dresser, OpenAI’s chief revenue officer, walked out after nine months.

Both women came from Salesforce. Voss was Slack’s chief revenue officer before she joined.

She had been building a plan. Voss told Fortune a month ago that her team was segmenting customers into groups, among them telecommunications, retail, consumer goods and manufacturing. Cybersecurity was a focus, along with driving adoption and showing businesses a return.

Her old boss welcomed her back in public

“Welcome Home to The Ohana @KaylinVoss!” Marc Benioff posted on X, linking to the story about her departure. The post has been seen more than 135,000 times.

Amir Efrati of The Information followed with three words that did the same job. “Kaylin is going back to… Salesforce.”

The new man starts this week

OpenAI named Dali Rajic as chief revenue officer in mid-August, replacing Dresser. It is the company’s fifth C-suite change in a year, Emily Forlini reported for Fortune.

Rajic, 53, was president and chief operating officer at Wiz, the cybersecurity company Google bought this year for $32bn. He starts this week.

OpenAI investor Josh Kushner introduced him to the company, CNBC reported. Greg Brockman made the hire, according to a source Fortune spoke to. Brockman took over the revenue organisation in early July, after Fidji Simo stepped down from the number two job to focus on her health.

Why OpenAI wanted him

Rajic ran sales at AppDynamics from 2012, rising to chief revenue officer, and helped pitch that company to investors before Cisco bought it for $3.7bn the day before its planned market debut. He then spent five years at Zscaler as president of go-to-market, and moved to Wiz in 2024.

“If OpenAI is behind on enterprise, he is definitely the guy,” said Jyoti Bansal, the AppDynamics co-founder who first hired him.

A source with ties to Anthropic called the recruitment a coup, Fortune reported.

The cybersecurity connection

Rajic has spent a decade selling security software. That matters, because OpenAI wants to sell a lot more of it.

The company pitches businesses on using its models to prevent hacks and breaches, under a programme called Daybreak. It expanded Daybreak into multiple access tiers on 10 August.

How he sells

Rajic treats sales as a science rather than an art, former colleagues told Fortune. He declined to comment for that piece but confirmed the details in it. He follows MEDDPICC, a framework built at PTC in 1996 that scores a deal on metrics, the economic buyer, decision criteria, decision process, paper process, identified pain, champion and competition.

The method also predicts which salespeople will work out, within months of them starting, by counting first meetings booked and demos run.

“You don’t hesitate, you move them out of the business,” one former colleague said of those who miss the mark. The goal is a “very disciplined, highly predictable, scalable go-to-market machine”.

That predictability is what investors want to see before a listing.

Rajic learned it from John McMahon, whom one source called the godfather of enterprise sales, at BMC Software in the early 2010s. Index Ventures partner Shardul Shah has a name for the alumni network that came out of PTC.

“In the world of go-to-market, the equivalent is the PTC Mafia,” Shah told Fortune, comparing it to the PayPal one. It includes MongoDB’s chief executive and revenue chief, and Datadog’s.

The man himself

Rajic was born in Yugoslavia, in what is now Croatia, moved to Germany aged one and came to the United States at 16. He studied at Cal Poly Pomona and took an MBA at Northwestern.

Colleagues describe him as blunt, intellectual and relentless. “We would call him the Croatian Sensation,” one told Fortune, recalling a man who grabbed two hard-boiled eggs at Starbucks on the way to a meeting and called it breakfast.

He does not work a room at parties and does not chase speaking slots. He has no X account.

The job he is inheriting

Dresser oversaw a commercial organisation of roughly 1,200 people and ran it from the road, meeting clients herself, Fortune reported. She worked through weekends and pushed for granular reporting the company did not have.

Current and former staff describe constant change over the past few years and say keeping up is exhausting.

OpenAI acknowledges the number of leadership changes and says it is normal for a fast-growing company. Rajic was picked to lead the next phase of growth, and there is a strong bench of senior leaders, a spokesperson said. Dresser did not respond to Fortune’s requests for comment.

What the turnover is happening around

Enterprise now brings OpenAI more revenue than consumers, a milestone it reached ahead of plan, CNBC reported this month. The company is chasing market share held by Anthropic.

Anthropic’s revenue passed OpenAI’s for the first time last quarter. It is also preparing a listing that could match SpaceX’s record, and could file as soon as next month.

OpenAI’s own chief financial officer told staff the company will go public in 2027, or sooner. On the current timeline, its main rival gets there first.

The question nobody at OpenAI will answer

Rajic lives in Austin with his wife and three children, and expects to spend much of his time travelling and in San Francisco.

“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 told Fortune. “That’s the open question.”

What has not been said

Neither Voss nor Dresser has given a public reason for leaving. OpenAI has not said who replaces Voss in the Americas, or whether the sales structure she was building survives her.

Salesforce has not said what role Voss returns to.