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.”
While Work-Bench evolved into a more traditional venture model, that first office became a hub where the firm hosted companies and events—around 200 a year, before the lease ended before COVID. “OG people in New York will remember that space very fondly,” Lin said. (Work-Bench still hosts monthly events, though usually at other tech companies’ offices, like Ramp.)
Lin and Lehr attribute Work-Bench’s longevity to its laser focus on sales, which is rooted in building community and serving as a connector between corporations and early-stage companies. “For the startups at pre-seed, and seed,” Lehr said, “customers are like oxygen, so you’re giving them the right intro at the right time, which helps them.”
It’s also knowing where to roll up their sleeves and help their portfolio companies, such as with the key zero-to-one challenge of building a customer profile and figuring out who to sell to. “The reality is that you can build a great product, but if you don’t have distribution as well, success is going to be very challenging,” Lin said.
Lehr said that around 50% of Work-Bench’s investments are in New York-based startups, with the firm typically focused on leading $2 million to $6 million pre-seed and seed rounds, though it will also do follow-on checks into Series A and B rounds.
Despite the continued fear over the liquidity crunch making it harder for venture firms to raise from limited partners, Lehr said that the fourth fund was Work-Bench’s smoothest raise yet, largely because of its consistent approach. “In some ways, we’re very boring,” Lin told me. “If you ask us, what’s new, quite frankly, nothing’s new.”
The caveat, of course, is the rise of AI, though Lehr noted that the hype around adoption has impacted deal sizes and company growth, but not necessarily sales cycles, which is Work-Bench’s bread and butter.
“We’re still doing exactly what we set out to do 12 years ago,” Lin said. “It’s just enterprise, seed, New York City, go to market.”
