CEO & founder at Brief
Drew Dillon
A 2x founder and product leader who learned the power of organizational clarity during a crisis. As Director of Product at Yammer and Principal PM at Microsoft, he saw how context drives execution. When thrust into emergency engineering leadership—managing remotely from San Francisco to Australia—he doubled team output with two-thirds the staff by focusing on why decisions get made, not just what gets built. Using this methodology his consultancy accelerated 20+ startups and now powers Brief, applying the same principles of strategic clarity to AI agents.
Questions & Answers
What sets you apart from others in your industry?
The prevailing wisdom is that infinite monkeys with keyboards will eventually jam out Shakespeare, that faster coding agents will solve product development. We fundamentally reject that notion. Brief isn't a coding agent; we're automated AI judgement and micro-targeted context that gives direction to your existing development tools.
What's a memorable 'aha' moment you've had while building your startup?
I started coding again this year for the first time in a decade and was hilariously successful because I micromanaged the hell out of the AI, constantly giving it context about business requirements, past decisions, and customer constraints. I discovered AI needs more than just needs better prompts, it needs the same institutional memory and strategic guidance I used to give human teams. We've since used Brief to build Brief, wildly outpacing what would've been possible withe a team of 10 without Brief.
How is your team uniquely positioned to solve the problem you're tackling?
I've personally guided teams through the exact chaos that AI agents create: brilliant execution in the wrong direction. After 15 years of translating business strategy into technical decisions, from crisis management to consulting 20+ startups, I know what context AI needs to be strategic, not just fast. We're encoding human product judgment into software.
