“We do want to be very mindful and intentional that we want to build software for the average person or software that enables more access to meaningful ways to make money,” she said. “I find in the current state, the metaverse and even web3 to a large degree, is not accessible just yet.” WorkLife does invest in web3 companies but only when the business has a strong stance on education or serving people beyond those who work in tech, she said.
At launch, WorkLife said that 40% of the new fund’s deals will come from SaaS School, a biannual workshop for entrepreneurs that Kimmel founded while at Zendesk. Now, it seems that Kimmel is taking a more expansive approach. She says WorkLife has already written five checks out of the new funds with an average check size of $2 million and post-money valuation at $20 million.
WorkLife’s first fund had an original target check size of around $150,000 per startup. That target would have given WorkLife room for about 33 deals. Fast forward, Fund I backed 97 companies, presumably with SPVs and smaller checks. All of the portfolio companies have raised follow-on capital from other firms.
The firm doesn’t track specific numbers on how many first-time founders it backs, but did say it writes first checks for operators who are leaving tech companies and starting their first companies. All but one of Kimmel’s investments have had a female founder, something she wants to take a “stronger stance on ensuring” in the second fund. There’s also a large focus on backing immigrants, something that Kimmel, a Ukrainian-American, says has stayed consistent since the firm’s debut.
WorkLife’s performance has largely been driven by a select group of unicorns in the portfolio, which include Deel, Webflow, Hopin, Tonal, Clubhouse, Pipe and Public.
Kimmel spoke about the layoffs saying that “those are very natural growing pains that happen over the course of a company’s history. A surprising thing that a lot of outside people forget is the fact that that growth from zero to $100 million in ARR was compressed into two years.” She pointed out that Hopin’s chief business officer Armando Mann has played an important role in hiring other executives to manage growth.
“With Clubhouse specifically, scaling any social network is incredibly hard,” Kimmel said. “I find that the platforms like Twitter where you already have distribution, that’s where you’re more likely to see the contribution rate from users be much higher.” That said, Kimmel pointed out that WorkLife has gone on to invest in Flow Club, a productivity-focused social networking app and Moment House, a live media platform for musicians.
With new millions behind Kimmel, the remote work category will get a surely appreciated chunk of focus and reality.