According to TechRepublic, OpenAI has poached Denise Dresser, the CEO of Slack, to be its first-ever Chief Revenue Officer. Dresser, who brings 14 years of Salesforce experience including leading Slack through its $27.7 billion acquisition, will spearhead global revenue and enterprise sales. This comes as OpenAI faces intense pressure, having burned through $2.5 billion in the first half of 2025 while generating $4.3 billion in revenue. The company is staring down a projected $74 billion in operating losses by 2028 and has committed to a staggering $1.4 trillion in infrastructure spending over eight years. Meanwhile, competition is fierce with Google’s Gemini 3 launch last month, and over 800 million weekly users now rely on ChatGPT.
The Money Problem Is Real
Let’s just state the obvious: OpenAI is spending money like it’s going out of style. A $2.5 billion burn in six months is almost incomprehensible for a company that isn’t building physical factories or a global delivery network. But that’s the new math of AI. Sam Altman’s revelation about $1.4 trillion in infrastructure commitments makes it clear they’re playing a capital-intensive, winner-take-most game. Dresser isn’t just being hired to grow revenue; she’s being hired to fund a war chest. The $74 billion in projected losses by 2028 isn’t a vague worry—it’s a countdown clock. Her job is to find the revenue to shrink that number, fast.
Enterprise or Bust
Here’s the thing: the path to salvation runs straight through corporate America. The stats tell the story. One million organizations are already using OpenAI tech, and ChatGPT Enterprise usage is exploding. When 75% of workers say AI saves them time and heavy users reclaim over 10 hours a week, you’ve got a product that sells itself on productivity. Basically, Dresser’s entire playbook from Slack—selling collaboration and efficiency to big companies—translates perfectly. She’ll be leveraging those same enterprise relationships, but now the pitch is about automating workflows, analyzing data, and, let’s be honest, potentially reducing headcount. It’s a powerful, if fraught, value proposition.
What This Means For Everyone Else
For users and developers, this hire signals a clear pivot. OpenAI is moving from a “cool research lab with a product” to a “ruthless commercial engine.” We’re going to see more structured enterprise packages, likely higher costs for heavy API usage, and experiments with advertising or tiered subscriptions. The free or cheap ride is probably ending. For the market, it intensifies the AI arms race. Google just launched Gemini 3, Microsoft is deeply embedded, and Anthropic is a serious contender. Poaching a sitting CEO from a major platform like Slack is a declaration that OpenAI is done playing nice. They’re bringing in a seasoned general for the revenue battle, because the innovation war is already too expensive to fight without one.
Can She Actually Do It?
It’s a hell of a challenge. Dresser knows how to sell software to businesses, but she’s never sold something that costs this much to deliver. The pressure is immense. Every dollar of revenue she brings in gets immediately eaten by compute costs. Her success hinges on scaling enterprise deals to a level that can offset losses most companies can’t even imagine. And she has to do it while fending off competitors with virtually unlimited resources. It’s a tall order. But if anyone in the SaaS world understands how to integrate a complex tool into the daily workflow of massive companies, it’s probably her. OpenAI didn’t just hire a sales boss. They hired a symbol. The era of pure research is over; the era of monetization is here.
