According to Silicon Republic, OpenAI has hired Slack CEO Denise Dresser as its new chief revenue officer, with Slack’s chief product officer Rob Seaman stepping in as interim CEO. Dresser, who spent over a decade at Salesforce and was named Slack CEO in 2023 after its $27 billion-plus acquisition, is tasked with accelerating enterprise AI adoption. OpenAI is on an aggressive spending spree, having inked deals worth more than $1.4 trillion recently, and its ChatGPT tool is nearing 900 million weekly active users. The company’s CEO of Applications, Fidji Simo, stated the goal is to put AI tools into the hands of “millions of workers.” Meanwhile, OpenAI CEO Sam Altman says the company is on track to generate over $20 billion in revenue this year but won’t be profitable until 2029, expecting to lose around $44 billion until then.
The Enterprise Land Grab Is On
This hire isn’t about tweaking a sales strategy. It’s a declaration of war for the enterprise software stack. Think about it. OpenAI has the tech, the hype, and the user base with nearly 900 million weekly ChatGPT users. But converting that into reliable, massive, enterprise-grade revenue is a completely different beast. That’s where Dresser comes in. Her entire career at Oracle, Salesforce, and Slack has been about scaling platforms that businesses can’t live without. She knows how to sell to CIOs, navigate procurement, and embed a tool into the daily workflow of a company. OpenAI isn’t just selling an API anymore; it’s selling a transformation, and it needs a general who’s done it before.
The Staggering Cost of Being a Leader
Here’s the thing that makes this all so fascinating. Sam Altman is openly saying they won’t be profitable until 2029 and will burn through about $44 billion getting there. That’s an almost incomprehensible sum. But they’re also projecting over $20 billion in revenue this year. So the game is clear: spend absolutely ludicrous amounts on compute and talent to stay ahead, and use hyper-aggressive enterprise sales to bring in enough cash to keep the engine running. The $1.4 trillion in “deals” they’ve signed? Those are likely commitments for cloud compute with providers like Microsoft. It’s a bet-the-company strategy, and hiring a CRO from the heart of the enterprise SaaS world shows they’re serious about the revenue side of that equation.
What This Means For Everyone Else
So what does this mean for the market? Basically, the AI platform wars just got a lot more expensive and sales-driven. For other AI startups, the bar for enterprise credibility just got raised. You’re not just competing on model performance; you’re competing against a sales machine that’s about to be built by someone who helped make Slack a household name in offices. For businesses, this push means AI tools are going to become more integrated, more “reliable,” as Fidji Simo says, but also probably more expensive and locked-in. It’s the classic cycle: innovation, then commercialization, then consolidation. OpenAI, with this hire, is sprinting into phase two. And the race to put an AI on every employee’s desktop just got a lot more real.
