What They Don't Tell You About Selling Your AI Startup | Jay Hack, ClickUp Head of AI

17 Jul 2026 · 60 min
59:59

In this interview, Jay Hack—Head of AI at ClickUp and founder of the CodeGen AI coding platform—walks through the journey from building a coding‑agent startup to its acquisition and integration into ClickUp. He explains how AI‑driven coding agents have evolved from narrow code generators into general‑purpose knowledge‑work assistants, and how ClickUp’s product teams now rely on AI agents (e.g., Cursor) to compress months of design‑to‑prototype work into a single chat message. Hack discusses the emerging "product generalist" role that blends product management, design, and AI‑prototyping, describing how hiring decisions focus on deep AI curiosity, side‑project experience, and the ability to ace AI‑augmented coding interviews. He shares his daily workflow of dog‑fooding ClickUp while simultaneously benchmarking multiple LLMs (Claude, Codex, Gemini, GPT‑5.x, etc.) using a personal open‑source eval suite called Galaxy Brain. Hack also offers founder advice: avoid overt pitching, instead craft narratives that let the audience arrive at the conclusion that the product is superior, and emphasize authenticity and integrated UI/knowledge‑graph experiences to reduce information fragmentation for agents. Throughout, he highlights practical tooling choices, the importance of unified context for org‑scale agents, and the cultural mindset required to thrive in an AI‑first organization.

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