OpenAI’s ex-head of sales becomes part of VC firm Acrew: She shares how OpenAI revealed to her the ways startups can establish a strong competitive edge

Aliisa Rosenthal Transitions from OpenAI to Venture Capital

Aliisa Rosenthal, who previously led sales at OpenAI, is embarking on a new chapter as a general partner at Acrew Capital. She will be collaborating with founding partner Lauren Kolodny and the rest of the Acrew team, as both Rosenthal and Kolodny shared with TechCrunch.

After dedicating three years to OpenAI—during which she played a role in launching products like DALL·E, ChatGPT, ChatGPT Enterprise, and Sora—Rosenthal departed the company about eight months ago. “Initially, I wasn’t seeking a role in venture capital,” she explained to TechCrunch. “I was spending my time meeting with numerous AI startups.”

However, after expanding OpenAI’s enterprise sales division from just two people to a sizable team, Rosenthal was intrigued when Kolodny introduced her to the possibilities of venture investing. Rather than focusing on the growth of a single company, she realized she could support a range of startups in developing their go-to-market strategies.

Reflecting on her experience at OpenAI, Rosenthal noted, “I gained valuable insights into buyer behavior, how organizations approach purchasing decisions, and the disconnect between what companies believe is achievable with AI and what they can actually implement today.”

Her background also gives her a unique perspective on how AI startups can establish defensible positions, especially as major players like OpenAI continue to release competing offerings.

“Will OpenAI eventually dominate every market and edge out all competitors? They’re already active in consumer, enterprise, and even hardware. But I don’t believe they’ll pursue every possible enterprise use case,” she observed.

Rosenthal believes that enterprise AI startups can differentiate themselves by focusing on specialized solutions tailored to specific needs.

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Context as a Competitive Edge

Rosenthal also emphasizes the importance of “context”—the data an AI system retains in its memory while processing tasks—as a crucial factor for startup differentiation.

“Context is flexible, scalable, and constantly evolving. We’re moving beyond traditional Retrieval-Augmented Generation (RAG) toward persistent context graphs,” she explained, referencing RAG, a widely used method for reducing AI hallucinations by training large language models on reliable sources and ensuring proper citations.

She points out that significant advancements are still needed in areas like memory and reasoning that go beyond simple pattern recognition.

“I anticipate real breakthroughs in this space. This year, we’re likely to see innovative approaches to context and memory,” Rosenthal predicted.

She believes that enterprise applications integrating advanced context management will have a significant advantage over competitors.

“Ultimately, the companies that control and optimize the context layer will hold a major advantage in the AI landscape,” she added.

Rosenthal also sees potential for startups that don’t rely exclusively on the most advanced—and expensive—models from major AI labs.

“There’s a market for more affordable, lightweight models that innovate on inference costs,” she said. While these models may not top every benchmark, they remain highly practical and cost-effective.

Her investment interests lie primarily in the application layer, seeking out startups with unique use cases or those leveraging AI to enhance enterprise productivity.

Building a Network and Seeking New Opportunities

To discover promising startups, Rosenthal plans to tap into her extensive network of OpenAI alumni. With OpenAI now a decade old, its alumni community has expanded, and many former colleagues have launched successful ventures, including high-profile companies like Anthropic and emerging players such as Safe Superintelligence.

There’s also a growing trend of former OpenAI leaders moving into early-stage investing. For example, Peter Deng, who previously headed consumer products at OpenAI, joined Felicis about a year ago and has since participated in major deals with startups like LMArena and Periodic Labs.

“I actually spoke with Peter a few months back, and his advice helped me decide to pursue investing,” Rosenthal shared.

Rosenthal’s strong relationships with enterprise AI users—potential buyers and beta testers—could give her an edge in sourcing and supporting early-stage startups.

She believes there’s still a significant gap in enterprise understanding of AI’s capabilities. “There’s a vast, untapped opportunity here, and I’m optimistic that new applications and companies will emerge to fill it,” she concluded.