ChatGPT is my daily tool, and I bet it’s yours too. So the news from OpenAI this week deserves a closer look than the usual boardroom drama as the IPO is inching closer, even if it’s actually a real boardroom drama. The company is losing senior leaders at the exact moment it is trying to look like a steady public company. A company that you can trust.
But if so, why are their leaders leaving the party? Don’t they trust the system they built?
The departures are piling up
Chief revenue officer Denise Dresser, the former Slack CEO who joined in December, is stepping down. Dali Rajic, currently president and COO at Wiz, takes her place. Brad Lightcap, OpenAI’s special-projects lead and former COO, is leaving too.
Add ethics chief Chloe Bakalar, communications chief Kate Rouch, and robotics lead Caitlin Kalinowski, who moved to Anthropic, left the company. The exits suddenly start to look like a pattern rather than a coincidence, and we are here, thinking what is this? What is happening?
The OpenAI safety team is getting thinner before the IPO
If this is not enough, the trend goes back further. Kevin Weil left in April. Safety systems lead Johannes Heidecke left in July, and OpenAI has disbanded its catastrophic-risk evaluation team, folding that work into existing departments. Applications chief Fidji Simo stepped back after medical leave. Co-founder Greg Brockman is taking more control and calls it a strategic realignment.
The uncomfortable part is that the company answering for AI safety is quietly running a smaller risk team right as the technology gets more powerful, and if you think this is maybe not the best idea, you’re probably right.
The money is huge, and that is exactly the tension
The balance sheet is where it gets interesting, because when you take a look at the numbers, everything clicks into place and shows us the big picture. And that’s not nice. OpenAI’s annualized revenue has jumped from about $24 billion to roughly $40 billion this month, helped by the GPT-5.6 launch. Its rival Anthropic grew even faster, from $9 billion at the end of 2025 to about $47 billion by May. OpenAI is reportedly preparing for a listing that could value it at up to $1 trillion, though sources now point to next year.
And on the other plate of the scale, there are those who are leaving.
So the contradiction is right in front of us. Record revenue, a trillion-dollar goal, and a steady stream of top people walking out the door. Not just any people, but important ones. An IPO wants stable executives and a story about risk that investors can defend. That the board can defend in front of investors and shareholders, and when there are new faces in the boardroom in every single quarterly meeting, defending becomes a hard task.
A talent drain, especially in safety, cuts against all. Bet your daily work on ChatGPT and you are betting on a company whose leadership is still being sorted out.
