OpenAI’s first gross sales chief, Aliisa Rosenthal, has discovered a brand new profession: enterprise capital. She’s becoming a member of Acrew Capital as a common companion, working alongside founding companion Lauren Kolodny and the agency’s different companions, Rosenthal and Kolodny inform TechCrunch.
Rosenthal left OpenAI about eight months in the past after a three-year dash on the AI lab that noticed the launch of DALL·E, ChatGPT, ChatGPT Enterprise, Sora, and different merchandise. “I wasn’t initially seeking to be a part of a VC fund,” she instructed TechCrunch. “I used to be on the market assembly with numerous AI startups.”
However after rising OpenAI’s enterprise gross sales crew from two folks to a whole lot, she noticed the enchantment when Kolodny pitched her on enterprise capital. As an alternative of serving to one startup with its go-to-market technique, she might assist a portfolio of them.
In her time at OpenAI, “I realized quite a bit about habits, each on the aspect of the consumers, how persons are occupied with these purchases, and the hole between what most organizations suppose is feasible and what they will truly deploy right now,” she mentioned.
For example, she has firsthand perception into what sort of moat an AI startup can construct that received’t depart it susceptible when mannequin makers like OpenAI launching competing merchandise.
Will OpenAI “simply construct the whole lot and put each firm out of enterprise? You realize, they’re doing quite a bit already: they’re in client, they’re in enterprise, they’re constructing a tool. I don’t suppose they’ll go after each potential enterprise utility,” she says.
So one moat is for enterprise AI startups to supply specialization.
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Context as moat
Moreover, she thinks the important thing to a very good startup moat can be “context” — or the knowledge the AI shops in its context window reminiscence as it really works on requests.
“Context is dynamic. It’s adaptable. It’s scalable. And I feel what we’re seeing goes past form of the fundamental RAG in the direction of this concept of a context graph, which is persistent,” she says referring to Retrieval-Augmented Technology (RAG) the de facto technique as of 2025 to reduce hallucinations by coaching LLMs on trusted, particular sources (and having the LLM cite them).
There’s nonetheless a number of tech that must be developed for this space, although, from reminiscence to reasoning past sample recognition.
“I anticipate actual innovation right here. I feel this yr we’ll see new approaches — the thought of context and reminiscence,” Rosenthal says.
However past startups working straight on context engineering, Rosenthal thinks enterprise apps that bake it in may have the benefit.
“In the end, after we discuss moat, I feel who owns and manages this context layer will develop into a big benefit for AI merchandise,” she says.
One other alternative she sees: startups not constructing atop a serious lab’s state-of-the-art fashions, with their excessive costs.
“I feel there’s room out there for cheaper fashions which can be lighter weight and innovate on inference prices,” she says. These are fashions that aren’t, maybe, on the high of the leaderboards of assorted benchmarks however “are nonetheless very helpful” and extra inexpensive.
“The place I’m actually excited to take a position is on the appliance layer. I’m actually excited by what would be the sturdy purposes constructed on all of those completely different fashions, not simply on the foundational fashions,” she says. She’s searching for startups with “attention-grabbing use instances” or that use AI to assist enterprise staff work extra effectively.
As for the place she’s going to seek out these startups, she’ll be working her community amongst OpenAI’s alums for starters. Now that the AI outfit is 10 years outdated, the alums community has grown. Many have already based startups which have raised massive bucks at excessive valuations, starting from OpenAI’s largest competitor, Anthropic, to buzzy early-stage corporations like Secure Superintelligence.
There may be additionally a rising precedent for high-level ex-OpenAI of us to develop into seed-stage traders. A few yr in the past, Peter Deng, OpenAI’s former head of client merchandise joined Felicis. He’s been crushing it ever since, and clearly having enjoyable, getting in on massive offers for decent startups like LMArena and Periodic Labs.
“I truly had a name with Peter a couple of months in the past, and he helped me make the choice,” Rosenthal mentioned of her option to develop into an investor.
However Rosenthal might have a secret weapon to win offers. She additionally has deep contacts amongst AI enterprise customers – the kind of consumers and beta testers these early AI startups want.
Enterprises nonetheless don’t perceive how a lot AI can do for them. “There’s a very massive hole that I’m very optimistic may be stuffed. It leaves an enormous inexperienced area for purposes and firms.”
