Finding my Way to Venture and Underscore VC

Please Welcome Gabby!

Like so many students, I spent much of my time at university uncovering the classes and activities that sparked my interest. And unlike so many of my peers, I had a particularly challenging time narrowing down the list — my breadth of interests is wide. I’ve always loved learning about new things and new people. In turn, I found myself taking classes across departments and building deep relationships with students and professors across campus.

With such a wide aperture, narrowing in on a career post-graduation seemed daunting. Nevertheless, having spent a chunk of time at Dartmouth doing behavioral marketing research, I pursued a career in go-to-market and ultimately joined the sales team at Klayvio in Boston. The role was fast-paced and the company was fast-growing and fun to be a part of. Starting my career in sales taught me so much — not only about understanding customer needs, but also about myself and that I loved working in fast-paced environments where there was always more to do, which probably comes from my time as a former hyper-competitive college lacrosse player.

While in my element at Klayvio, I continued to attend local events or panels that sounded interesting as a way to connect with new people and ideas. Serendipity landed me at an event that featured a panel of women in VC. The women shared their experiences in venture, and, while many aspects of their roles were similar to my day-to-day in sales, the different elements to the roles excited me and was the impetus for my career pivot into investing at OpenView.

While I seemingly stumbled into investing, so much about venture capital organically aligns to my wide array of interests and my competitive nature. This career path calls for insatiable curiosity, a broad view of multiple markets and business-building methodologies, and a strong drive to win.

I worked at OpenView to identify and evaluate Series A and B investments in enterprise application software companies and businesses with a product-led growth go-to-market strategy. While at OpenView, I got to connect and build relationships with so many amazing founders and support our diligence work on prospective investments, including the firm’s investment in Voiceflow. My time at OpenView solidified my interest in this industry and that it was a role I really wanted to pursue.

Today I’m incredibly excited to share that I’m taking my next step in my VC journey, joining the team at Underscore VC! Underscore’s community-driven and people-first approach to venture is unique. As I met more and more of the team, the opportunity began to feel like a perfect fit. They are a group of very talented investors and people from whom I am excited to learn.

At Underscore, I’ll be working to source and evaluate potential new investments in the B2B software space. Excitingly, my focus will be up-stream from my previous experience, as we invest at the Pre-Seed and Seed stage. I will also be largely focusing on uncovering and supporting founders across Boston’s academic institutions.

If you’re beginning to explore a new idea, working through challenges with go-to-market, or interested in learning more about how to get value from the deep experience of the Underscore Core Community, please reach out.