We've developed a detailed new product-market fit framework for B2B founders

Bill Trenchard


The best insights come from paying attention to the small things.

But, if you’re looking for extraordinary outcomes, it’s not enough to simply have the insight. You also have to view it, inspect it, through a different-colored lens. Doing what’s always been done is never the path to innovation.

The idea of starting small, then building up and out, is one that cuts across all aspects of my life. I started Jump Networks in the late ‘90s after recognizing the potential of the internet and thinking of ways that people could improve on the smallest unit of their lives: their time. Based on that idea, I built the world’s first connected online organizer, which was eventually acquired by Microsoft.

This idea cross-pollinates my investing decisions as well. I look for founders who are first principles thinkers — eager to break down incredibly complex problems to the smallest unit and build unconventional solutions to them. That’s why I was an early investor in startups like Uber, Looker, Verkada, Flexport and Together AI.

My hope, as an investor, is to coach these founders and startups to the edges of their potential by sharing my unwavering support and unvarnished opinions, and by helping them peek around the corners based on my own experiences as an entrepreneur.

As a founder, operator, advisor and angel investor, Bill has helped dozens of companies launch, manage through hyper growth and win. Before joining First Round, Bill led LiveOps to $100 million in sales and hundreds of employees as the industry’s leading cloud contact center. He also founded Jump Networks, a leading web calendar and personal organizer acquired by Microsoft.

As an angel investor and Founder Partner at Founder Collective, Bill made investments in category killing companies including Uber, IronPort (acquired by Cisco), Adroll, PowerSet (acquired by Microsoft), Lending Club, HomeRun (acquired by Rearden Commerce), Tapulous (acquired by Disney), Slide (acquired by Google), and Chegg.

At First Round, Bill has led investments in companies including Looker, Flexport, Verkada, Superhuman, Together AI, EvolutionIQ, Promise, and Omni.

Bill has a Bachelor of Arts in science and technology studies from Cornell University.