12 years ago, Jessica Lin and Jonathan Lehr made a bold bet on Silicon Valley venture capital: Most investors were trying to fit a square peg in a round hole. They saw VCs sniffing around the Google and Facebook campuses to find some new startup, which would then inevitably need to find early customers at Fortune 500 companies like JP Morgan. Lin and Lehr had the idea to flip the model of software investing by starting with the customer community, figuring out their pain points, and then finding the best early startups solving that problem. “We’re not trying to buy a lottery ticket to find the next Facebook,” Lehr told me. “Within the enterprise, you can make it a game of 3D chess.”
The natural place to test out the thesis was New York, where a concentration of enterprise software customers is based, so that’s where Lin and Lehr started Work-Bench over a decade ago with a $10 million first fund. The bet has paid off. Work-Bench just closed a $160 million fourth fund with the same operating framework as its first, just at a much larger scale, and in a far more mature New York tech ecosystem. “We figured startups should build near their customers,” Lehr said from Work-Bench’s offices near Madison Square Park. “Thankfully, that has played out.”
