OpenAI has quietly brought on board the co-founders of Context.ai, a startup known for building AI model evaluation and analytics tools. The move, announced Tuesday, signals a fresh push by OpenAI to enhance how developers assess the performance of large language models.
Following the acquisition, Context.ai will begin winding down its operations, according to a farewell note on its website. Although OpenAI hasn’t disclosed financial details of the deal, it appears the goal is to integrate Context.ai’s expertise directly into OpenAI’s own evaluation efforts.
Founded in 2023 by ex-Google engineers Henry Scott-Green and Alex Gamble, Context.ai set out to solve a growing pain in the AI ecosystem: understanding how models behave in the real world. Their seed round raised $3.5 million from GV (Google Ventures) and Theory Ventures, enabling them to develop products that helped AI developers track, tag, and analyze model outputs with real-time feedback.
One of Context.ai’s standout tools was an analytics dashboard. It allowed users to explore how their models responded to prompts, identify trends, and understand whether the answers being generated were actually useful. Through an API, developers could upload transcripts, and Context.ai would then categorize them by topic or relevance—adding clarity to what was often described as a “black box” experience.
Scott-Green, now officially a product manager at OpenAI, shared in a post on X that he and Gamble will focus on building developer tools specifically aimed at model evaluation. He emphasized the importance of having reliable evals to create truly high-performing AI systems, a mission the pair will now continue from inside OpenAI.
As of August 2023, Context.ai had a small team of just six employees. It’s currently unclear how many will join OpenAI as part of the transition, but the acqui-hire underscores OpenAI’s intent to invest heavily in improving how developers monitor and assess their AI systems.
In the startup’s parting message, the team reflected on their two-year journey: “Evals are essential for building high-performing AI apps, but they’re hard to get right. We’ve spent years tackling this at Context.ai and couldn’t be more excited for this next chapter.”
By absorbing Context.ai’s talent and tech, OpenAI is making a strategic bet on transparency, performance tracking, and user-centric tools—vital components in the next evolution of generative AI development.
