3x founder
Drew Dillon
Product Unc | Co-founder of Brief | AI Ships. Brief Navigates. | a16z speedrun (sr005)
Experience
Career
2025Brief
FounderCEO and Founder · San Francisco, California, United States · 2025 – Present
2024Mocksi
Co-founderCEO and Co-founder · San Francisco Bay Area · 2024 – 2025
2018ProductBridge
Principal · San Francisco Bay Area · 2018 – 2024
2020Burb
FounderFounder · San Francisco Bay Area · 2020 – 2023
2018Skedulo
Advisor · San Francisco Bay Area · 2018 – 2019
- 2017
Skedulo
Chief Product Officer (Product, Engineering, and Design) · San Francisco Bay Area · 2017 – 2018
2013Fond, formerly AnyPerk
VP of Product, Engineering, and Business Development · San Francisco Bay Area · 2013 – 2017
2012Microsoft
Principal Program Manager Lead · San Francisco, CA · 2012 – 2013
2010Yammer, Inc.
Director of Product Management · San Francisco Bay Area · 2010 – 2013
2008SafeNet
Senior Product Manager, Data Protection · 2008 – 2010
- 2007
Ingrian Networks
Product Manager · 2007 – 2008
- 2005
Ingrian Networks
Systems/Sales Engineer · 2005 – 2007
2003SAIC
Systems Engineer · 2003 – 2005
Bio
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.