Former OpenAI sales chief joins Acrew Capital as partner

Aliisa Rosenthal, OpenAI’s former head of sales and go-to-market strategy, has joined Palo Alto venture firm Acrew Capital as a partner, bringing insider knowledge of how startups can compete against the San Francisco AI giant.

Rosenthal spent three years at OpenAI, where she helped build the company’s enterprise sales operation and watched the ChatGPT maker expand into new markets. Now she plans to use that experience to help startups find areas where they can build defensible businesses despite competition from well-funded AI model makers.

“I saw firsthand where OpenAI focused its resources and where it didn’t,” Rosenthal said in an interview. “There are still plenty of opportunities for startups to build meaningful businesses, but they need to be strategic about where they compete.”

The hire reflects Silicon Valley’s ongoing talent shuffle as executives from major AI companies move into investing roles. Rosenthal joins a growing list of former OpenAI employees who have transitioned to venture capital, including former research scientist Dario Amodei, who left to start Anthropic before that company raised hundreds of millions in VC funding.

Acrew Capital, founded in 2019, manages $500 million across two funds and focuses on early-stage enterprise software companies. The firm has backed 40 companies, including several in the technology sector that compete adjacent to OpenAI’s core products.

“Aliisa brings a unique perspective on how enterprise customers actually adopt AI tools,” said Lauren Kolodny, Acrew’s co-founder and managing partner. “She understands both the technical capabilities and the practical limitations that create opportunities for focused startups.”

Rosenthal’s appointment comes as Bay Area venture firms scramble to understand the AI market’s rapid evolution. OpenAI’s $157 billion valuation has created pressure on smaller AI companies to prove they can build sustainable businesses rather than features that larger companies might easily replicate.

During her tenure at OpenAI, Rosenthal oversaw partnerships with major enterprise customers and helped launch several commercial products beyond ChatGPT. She previously worked in business development roles at Palantir and McKinsey & Company after earning her MBA from Stanford Graduate School of Business.

“The enterprise sales cycle taught me which use cases customers actually pay for versus which ones they just experiment with,” Rosenthal said. “That distinction is crucial for startups trying to build real businesses.”

Acrew has already invested in several AI-adjacent companies, including workflow automation startup Zapier and data infrastructure company Hex. The firm typically writes checks between $1 million and $5 million for Series A and B rounds.

Rosenthal said she will focus on enterprise software companies that use AI as a component rather than competing directly with foundation model makers like OpenAI, Anthropic, and Google. She pointed to opportunities in vertical-specific applications, workflow automation, and data infrastructure.

“The companies that succeed will solve specific customer problems rather than trying to build general-purpose AI,” she said. “There’s a big difference between having impressive technology and having a business customers will pay for.”

The venture capital market for AI startups has remained active despite broader tech funding challenges. Bay Area AI companies raised $12.4 billion in 2024, according to PitchBook data, with much of that concentrated among a handful of high-profile model makers.

Acrew’s portfolio companies have raised more than $2 billion in follow-on funding since the firm’s launch. The firm’s other partners include former Salesforce executive John Roos and ex-Google product manager Vishal Lugani.

Rosenthal will split her time between Acrew’s Palo Alto headquarters and meeting with portfolio companies across the Bay Area. She said her experience at OpenAI gives her insight into which markets the AI leader plans to enter and which it will likely avoid.

“Startups need to understand where the big players are heading so they can position themselves accordingly,” she said. “Sometimes that means avoiding direct competition, and sometimes it means building something complementary.”

The transition reflects broader changes in Silicon Valley’s AI ecosystem as the initial ChatGPT hype gives way to more practical considerations about building sustainable businesses. Venture firms are increasingly looking for partners who understand both the technical possibilities and commercial realities of AI adoption.

Rosenthal starts her new role immediately and said she has already begun reviewing potential investments. Acrew typically takes six to nine months to close deals after initial meetings with startup founders.

“The next wave of successful AI companies will be those that focus on customer problems first and technology second,” she said. “That’s where I see the biggest opportunities for venture returns.”