Hylak designed interfaces for Apple's Vision Pro before co-founding Raindrop, which watches AI agents in production and shows teams where they quietly fail users.
Ben Hylak is a co-founder of Raindrop, a San Francisco, California, company that monitors AI agents in production, finds failures such as wrong tool calls or forgotten instructions, and groups them so teams can fix them.
Designing visionOS at Apple
He interned twice in avionics engineering at SpaceX, according to his personal site. At Apple he started as an engineer and moved into design, spending four years on the Human Interface team building visionOS, the software behind the Vision Pro headset, according to his Y Combinator profile. He has said one lesson from leaving Apple was that a startup has to win attention that Apple products get by default, in an interview with Creative Conviction.
Starting Raindrop After Sidekick
After ChatGPT launched, he began building with Zubin Koticha, his close friend and former roommate, and Alexis Gauba, who had co-founded the crypto company Opyn with Koticha. Their first product was Sidekick, a coding assistant. They struggled to see where their own agents failed in production, built tools to find out, and realized every team shipping agents had the same problem. That work became Raindrop, which went through Y Combinator's Winter 2024 batch.
Personal Life
He lists camping, scuba diving, writing poetry and karaoke among his interests, along with Kurt Vonnegut and Paul Simon.
