Aliisa Rosenthal, OpenAI’s first sales leader, has transitioned from the AI lab to venture capital, joining Acrew Capital as a general partner. She left OpenAI about eight months ago after a three-year tenure that included helping scale the company’s enterprise sales team from two to hundreds of employees and supporting the launches of major products like DALL·E, ChatGPT, ChatGPT Enterprise, and Sora. Rosenthal initially wasn’t looking to join a VC firm. She had been meeting with numerous AI startups and was drawn to the opportunity when Acrew’s founding partner Lauren Kolodny pitched her on the role. Instead of focusing on go-to-market strategy for a single company, she’ll now support a portfolio of startups. During her time at OpenAI, Rosenthal gained deep insights into enterprise buyers’ behavior and the gap between what organizations believe AI can do and what they can realistically implement. This experience shaped her view on how startups can build defensible advantages, or “moats,” in a competitive landscape where giants like OpenAI are expanding into consumer, enterprise, and hardware. She believes one strong moat lies in specialization. While OpenAI is building broad capabilities, including consumer products and devices, Rosenthal doubts it will target every enterprise use case. That creates space for startups to focus on niche verticals and deliver tailored solutions. Another key area she sees as critical is context. She emphasizes that the ability to manage and leverage context—especially persistent, dynamic context across interactions—will be a major differentiator. This goes beyond basic Retrieval-Augmented Generation (RAG), evolving toward what she calls a “context graph.” She expects innovation in memory systems, reasoning, and long-term knowledge retention to drive new opportunities. Rosenthal also highlights a growing market for lightweight, cost-effective AI models. While not leading in benchmark scores, these models offer practical value at lower inference costs. She’s particularly interested in startups that build durable applications on top of various models, not just foundational ones. She plans to tap into her network of OpenAI alumni, a growing community of former employees who have gone on to found high-profile startups like Anthropic and Safe Superintelligence. The trend of ex-OpenAI leaders entering early-stage investing is also on the rise, with figures like Peter Deng of Felicis making strong moves. Rosenthal’s unique edge may be her direct access to enterprise buyers—key early users and testers for AI startups. Many organizations still underestimate AI’s potential, leaving a vast opportunity for companies that can bridge the gap between promise and practical deployment. She’s optimistic about the future of AI applications and sees a fertile landscape for innovation.