Lily Lyman has been an entrepreneur, an operator at a massive tech company, and now she's making a move to the other side of the table: venture capital.
After spending nearly three years at Facebook, Lyman has joined Underscore.VC as principal, making her the first woman to join the Boston venture capital firm in a senior role after co-founder C.A. Webb left early last year. Lyman joins the firm as women in senior positions still constitute a small fraction at VC firms. A study from Prequin last fall found that women only make up 21 percent of employees and 11 percent of senior roles at VC firms globally.
Lyman is acutely aware of the lack of diversity in tech, having worked on a team at Facebook that was 90 percent male — something she hopes to change on a broader level in Boston.
"I think Boston has a little bit of homogeneity in it," Lyman told BostInno in an exclusive interview. "We definitely need to create an environment that feels inclusive and part of that is just mindfulness and proactively trying to build it."
While Lyman has spent most of the last five years in California, she is no stranger to Boston. With most of her extended family from the area, she went to a local high school and then got her bachelor's at Harvard. A few years later, after moving to the West Coast and getting her MBA at Stanford, Lyman co-founded a consumer packaged goods startup called NECT that she operated in Boston for a while with her business partner.
The startup ultimately failed after running for a year and a half — Lyman said she and her co-founder made the decision after realizing "the unit economics were tough and it wasn't going to be the business we wanted it to be." Regardless, the experience was valuable, especially now that's she's in a position to work with early-stage startups.
"I think it gave me a lot of respect and empathy for that zero-to-one grit phase," Lyman said.
"I like to build so Underscore.VC felt like a way to get my hands dirty and be a builder."
When NECT ended, she returned to Facebook after having done an internship there a few years before while at Stanford. During her roughly three years at the Menlo Park tech giant, Lyman was a program manager on the business development and partnerships team, where she worked with telecom companies across the world. She also worked on products for emerging markets, including Facebook Flex, an alternative version of Facebook for low-connectivity environments that grew to about 50 million users across 65 countries in three years.
Lyman said there were a few big reasons she joined Underscore.VC. For one, she found the firm's focus on creating alignment between investors and entrepreneurs to be authentic, "which I think is hard to find." She liked that the firm's members were experienced entrepreneurs themselves who ran the firm in a similar fashion. There is also the firm's core community, a group of hundreds of entrepreneurs who aid the firm and their portfolio companies.
"I like to build so Underscore.VC felt like a way to get my hands dirty and be a builder, both as an investor but also thinking about what that means for venture," Lyman said.
Starting out, Lyman will serve as a board observer for three of Underscore.VC's portfolio companies, marketing tech startups Zaius and Mautic and smart city startup Soofa. She said she hopes to help build out the firm's thesis of "trusted cloud intelligence" while using her experience in telecom and mobile applications to focus on "top of stack" opportunities, including business software and frontier technologies like augmented reality and machine learning.
Lyman said she started talking to Underscore.VC about the principal role last August as she and her husband were in the process of moving to Boston, where her husband is from and where she worked for Facebook in her final months. Coming from Silicon Valley where venture capital funding trumps all other metro regions, Lyman sees a lot of opportunity here.
"It's naturally smaller, but I think, as a result, that makes it more collaborative, more community-oriented and allows you to know a lot of the folks," Lyman said. "I think the trick of that will be how do you preserve that but also keep it dynamic so that it's inclusive of new folks and new talent and new ideas."
