Ask AI & @Brain

Live at ClickUp
2025 — Present

The AI system inside ClickUp's everything app

#1Quality Score
Multiple xUsage Growth
Multiple xRevenue Growth

The Story

After the Stepsize acquisition, the team and I joined ClickUp to keep building toward the same vision. After a decade of working on this problem, we were finally at a company with the scale and the product to make it real. Brain is ClickUp's AI system, and we shipped two products within it. Ask AI is a ChatGPT-like assistant built into the platform. @Brain is an AI agent you can mention anywhere in ClickUp, like you would a teammate. Think of it as giving every team an AI colleague who actually knows what's going on.

We built the @Brain agent from scratch as a 0→1 product using RAG and 35+ tools. An early version of Ask AI existed when we arrived, but it had limited capabilities and quality wasn't where it needed to be. Together with some brilliant new friends at ClickUp, we rebuilt it.

"Now you can mention @Brain like a human teammate" — ClickUp

The Hard Part

ClickUp pitches itself as the everything app for work. The vision for Brain was that it should be able to do anything a user can do in this everything app, with access to all relevant context, while respecting user privacy and permissions and still providing high quality answers in a timely fashion. That's a huge challenge. ClickUp's data model is deep: tasks, docs, comments, custom fields, relationships between all of them. If Brain couldn't understand that context, it would just be another chatbot giving generic answers. So we built a system with 35+ specialised tools and RAG that grounds every response in real workspace data. The AI doesn't guess. It looks things up, takes actions in the app on behalf of the user, and does all of it while respecting their privacy and permissions. Getting that last part right was one of the hardest problems we solved.

What Happened

Positive ratings of Ask AI responses basically doubled, and it became ClickUp's most used AI feature. @Brain became ClickUp's highest quality AI feature. Usage and revenue from these AI features grew multiple times over. Millions of people use it daily. After a decade of betting on this future, it was pretty special to see it working at that kind of scale.

Role

AI Product Lead · @Brain 0→1 · Transformed Ask AI

Achievements

Highest quality & usage AI features

Tech Stack

RAG · 35+ Tools · LLMs · Proprietary Agent Harness