OpenAI just hired one of Silicon Valley’s most made-for-this-moment operators. Denise Dresser, who ran Slack after a long career inside Salesforce, is leaving the collaboration app to become OpenAI’s first chief revenue officer — a role that, on paper, reads like a declaration of intent: turn a wildly popular AI research lab into a dependable, enterprise-grade revenue machine.

Dresser’s résumé is the kind of thing boardrooms hand around when they want to stop treating AI as a curiosity and start treating it like infrastructure. She spent more than a decade at Salesforce in senior sales roles and took the reins at Slack in 2023, shepherding the product through tighter integration with Salesforce and a push to make Slack less of a siloed chatroom and more of a place where work actually happens. That experience — selling cloud software into Fortune 500 accounts while adding AI features that live inside tools people already use — is exactly the skill set OpenAI needs right now.

For OpenAI, hiring a CRO is more than an org-chart tweak. The company has been on a product-first growth tear: millions of free ChatGPT users, huge developer interest, and an ecosystem of partners from Microsoft to assorted platform vendors. But the hard work of turning pilots into contracts that pay every quarter is different from getting a product to go viral. Dresser will be responsible for building that bridge — formalizing go-to-market teams, tightening customer success, and converting exploratory bets into repeatable revenue streams. The company has already said more than a million businesses use its tools, and ChatGPT’s weekly active user numbers now sit in the hundreds of millions; OpenAI needs someone who understands how to monetize that scale without killing the product’s momentum.

What Dresser knows is how to translate workplace buzz into buying behavior. At Slack, she oversaw the rollout of AI features aimed at making hectic channels usable again: auto-summaries, clearer language transforms, and smarter assistants that can pull context from a messy thread. Those product moves were never about novelty; they were about reducing friction in the day-to-day work of customer support teams, finance groups, and engineering squads — the exact audiences that enterprise sales teams want to reach with predictable, multi-year contracts. OpenAI’s bet, plainly put, is to embed its models inside those workflows rather than ask companies to adopt yet another standalone app.

The timing also matters. OpenAI’s growth story has been dizzying — massive user engagement, a lucrative partnership with Microsoft, and product launches that litter headlines — but so have its costs: cloud bills, chips, and the operational overhead of serving huge model workloads. Turning popularity into profit is a different discipline. Appointing a seasoned revenue chief signals to investors and partners that OpenAI is serious about predictable, contract-driven income, not just subscription bursts or developer curiosity. Expect to see tighter vertical packaging — finance, customer service, software engineering — and more deals that look like classic enterprise SaaS buys.

Slack, meanwhile, has to absorb the shock. Dresser’s exit leaves the messaging service at a fragile moment: it’s still competing with Microsoft Teams and a new crop of AI-native collaboration tools, and customers are weighing whether Slack’s AI recaps and search are worth extra spend. Salesforce product chief Rob Seaman will step in as interim CEO, a move that buys continuity but also raises the question of who will lead Slack through its next, AI-heavy chapter. For employees and customers, leadership churn is noise; for sales teams and partners, it’s the kind of uncertainty that can slow buying decisions — precisely the friction OpenAI hopes to smooth out on the other side.

There’s a larger industry pattern here: the smartest route to adoption is not “build a new world,” it’s “make AI an invisible helper inside the world people already have.” OpenAI’s move to recruit someone fluent in selling extensions to existing workflows — rather than pitching a whole new platform — underlines that reality. Dresser helped translate Slack’s marketing messages into commercial deals; OpenAI wants her to do the same on a much larger scale, taking pilots that show promise and turning them into enterprise-wide purchases that stick.

That does not mean product teams get sidelined. If anything, this hire forces a closer marriage between product and sales: packaging needs to be repeatable, SLAs need to be clearer, and legal and security pipelines must be frictionless if companies are going to hand over internal data and mission-critical workloads to a model provider. OpenAI’s existing work with Azure and Microsoft is a head start, but Dresser’s job will be to ensure sales cycles are predictable and the handoff between trial and enterprise deployment isn’t a hand grenade of complexity.

For the market, the hire is a signpost that the AI era is moving into boring, very lucrative territory: contract renewals, customer success metrics, churn rates, and annual recurring revenue. Those aren’t sexy headlines, but they’re what separates hype from a durable business. Investors, cloud partners, and big customers will all be watching to see whether OpenAI can convert its cultural momentum into the kind of financial predictability expected of legacy enterprise vendors. If Dresser succeeds, the company will have shown that you can scale both wonder and wonky operational discipline at the same time.

There’s risk too. Bringing in a sales-heavy executive can invite pressure to prioritize short-term contracts over long-term product health. The best-case scenario is what Dresser did at Slack: make AI feel like a natural extension of the tools people already use, and let real productivity gains sell themselves. The worst-case is familiar: monetization that creates vendor lock-in, rushed features that break trust, or pricing moves that alienate the very developers and small teams who made ChatGPT a cultural phenomenon in the first place. How OpenAI balances those pressures will probably determine whether this hire is remembered as the moment the company grew up — or the moment it changed into something else.

Whatever comes next, the hire signals a new phase for AI companies: the sprint to find product-market fit is giving way to the marathon of building repeatable enterprise economics. Denise Dresser’s move from Slack to OpenAI isn’t a personal footnote so much as a statement of intent — that the era of AI is entering the less glamorous, more consequential work of turning wonder into workaday value.