Silicon Valley has witnessed an intriguing executive shuffle.
OpenAI landed Denise Dresser, Slack’s CEO, as its first-ever chief revenue officer in a power play that signals massive changes ahead. This development could help the ChatGPT maker prepare for its next phase of growth.
Dresser brings 14 years of Salesforce expertise to the table, including her leadership through Slack’s $27.7 billion acquisition. She’ll be busy, and not ‘Slack-ing’, as OpenAI faces mounting financial pressures and fierce competition from tech giants.
The AI wars
Dresser will spearhead global revenue strategy and enterprise sales at a company that’s bleeding money faster than almost any startup in history. OpenAI burned $2.5 billion in the first half of 2025 while generating $4.3 billion in revenue—a 16% jump from all of 2024.
The stakes couldn’t be higher. OpenAI faces a staggering $74 billion in projected operating losses by 2028—that’s nearly 75% of expected revenue. Meanwhile, CEO Sam Altman revealed the company has committed to $1.4 trillion in infrastructure investments over eight years—a mind-boggling sum that makes Dresser’s revenue expertise absolutely crucial.
Competition is intensifying rapidly. Google unleashed Gemini 3 last month, while Microsoft and Anthropic continue advancing their own AI offerings. OpenAI’s early ChatGPT advantage, launched just over three years ago, faces unprecedented pressure from established tech titans with deeper pockets.
The enterprise gold rush
OpenAI’s enterprise momentum is undeniable. More than one million organizations now use OpenAI technology, including corporate giants like Walmart, Morgan Stanley, and Target. ChatGPT Enterprise witnessed an eightfold rise in weekly interactions, demonstrating explosive demand for workplace AI integration.
If you’ve ever wished your workday could be shorter, Dresser’s hire might make that reality. Or you’ll lose your job, as some companies prefer to make cuts. The productivity numbers show 75% of workers report AI improved their work speed or quality, with many saving 40-60 minutes daily and heavy users reclaiming more than 10 hours weekly. These metrics explain why OpenAI views enterprise sales as its financial salvation.
Dresser will be reporting to COO Brad Lightcap. Her appointment reflects a broader industry shift toward commercial AI viability rather than pure research innovation. With ChatGPT now serving over 800 million weekly users, the pressure to monetize effectively has never been more intense.
Dresser’s proven track record leading Slack through its Salesforce integration positions her well to help OpenAI’s enterprise transformation. The appointment comes as OpenAI explores revenue diversification beyond enterprise licensing, with early discussions about advertising, tiered subscriptions, and structured commercial packages.
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