Jeffrey Ip

Jeffrey Ip is co-founder and CEO of Confident AI, an LLM evaluation and observability platform built around DeepEval, the open-source framework he created. With cofounder Kritin Vongthongsri he joined YC Winter 2025 after growing DeepEval through open-source adoption, then closed an oversubscribed seed of about $2.2 million with participation from Y Combinator and other funds.

From Google and Microsoft to DeepEval

Ip previously worked as a software engineer at Google on YouTube Creator Studio infrastructure and at Microsoft on document recommenders for Office 365. He started DeepEval so engineers could write use-case-specific evaluation metrics the way they write unit tests. On the company site he has described the open-source package as the engine behind Confident AI's cloud workflows for datasets, CI evals, production monitoring, and red teaming.

Bootstrapping into YC

In a fundraising post Ip wrote that DeepEval's growth is what got the company into YC even while better-funded observability vendors spent heavily on ads. "What started off as a bootstrapped open-source package became the thing that got us into YC," he said. He credits interviewer Tom Blomfield with seeing that the team was still growing despite staying bootstrap-first for a long stretch.

On owning the evaluation layer

Confident AI's thesis is that evaluation quality has to be as rigorous as the application itself, which is why DeepEval stays open source while the commercial product handles collaboration, monitoring, and governance. Looking ahead after the seed, Ip wrote: "We're going to double-down on providing the best LLM evaluation for everyone." That includes educating new teams on practical eval practice and expanding safety testing through DeepTeam inside the same ecosystem.