According to Wired, Slack CEO Denise Dresser is leaving the company to join OpenAI as its new chief revenue officer, starting next week. Salesforce CEO Marc Benioff announced her departure in a message to staff. Dresser, who has been at Slack for 14 years and was appointed CEO in 2023, will manage OpenAI’s rapidly growing enterprise unit and report to COO Brad Lightcap. OpenAI’s CEO of Applications, Fidji Simo, stated the hire is about putting “AI tools into the hands of millions of workers.” Slack’s current chief product officer, Rob Seaman, will become the interim CEO. The company was acquired by Salesforce for nearly $28 billion in 2021.
OpenAI’s Big Business Blitz
This hire isn’t subtle. It’s a cannonball into the deep end of the enterprise software pool. OpenAI has been on a tear this year, signing huge deals with companies and pushing its enterprise tier hard. But there’s a big difference between having a hot product that IT departments adopt and building a disciplined, global sales machine that can compete with the likes of Salesforce, Microsoft, or Google. That’s exactly what Dresser is being brought in to do. She spent years in Salesforce’s enterprise sales unit before leading Slack. She knows how to sell to CIOs and navigate massive procurement processes. OpenAI’s tech might be magical, but enterprise budgets are ruthlessly practical.
Why This Timing? Why Now?
Here’s the thing: the low-hanging fruit for ChatGPT is probably gone. The developer community is hooked, and early-adopter companies have already signed up. The next phase is the hard, unglamorous work of scaling a sales org, building industry-specific solutions, and embedding AI into the boring, critical workflows of Fortune 500 companies. They need a seasoned operator who’s done this before, and they need her yesterday. With competitors like Anthropic and a host of well-funded startups also chasing enterprise dollars, plus Microsoft’s deep integration, this is a land grab. Hiring a sitting CEO from a major collaboration platform signals they’re serious about winning it.
What It Says About Salesforce and Slack
Let’s be honest, this also feels like a bit of a poach from Salesforce. Dresser was a Salesforce exec who moved over to run one of its biggest acquisitions. For her to leave for OpenAI, of all places, is telling. It suggests the center of gravity for enterprise software innovation has decisively shifted to AI-native companies. And what about Slack? The messaging platform has seen its founding team depart and has been gradually absorbed into the Salesforce mothership. Having your CEO leave after just over a year in the role doesn’t scream stability. It raises questions about Slack’s strategic independence and its own AI ambitions. Was this a can’t-miss opportunity for Dresser, or a sign she wanted off a potentially sinking ship?
The Battle for the Enterprise Desk
So what’s the endgame? OpenAI is assembling the pieces to become a full-stack enterprise AI vendor. They have the models, the platform, the developer ecosystem, and now a seasoned enterprise sales leader. They’re not just an API company anymore; they’re building a direct sales force to go after the biggest contracts. This puts them on a more direct collision course with Microsoft, Google, and even parts of Salesforce. The real test will be whether Dresser can build a sales culture that can execute at scale. Can she translate OpenAI’s research brilliance into reliable quarterly revenue? That’s the billion-dollar question. Actually, given the valuations here, it’s probably the trillion-dollar one.
