3 min read

Why Underscore?

Software Engineer Turned PM Turned Venture Capitalist

I’m thrilled to share that I’ll be joining the Underscore team as their newest Investment Associate! As a software engineer turned product manager turned venture capitalist, I’m excited to be investing in a Boston ecosystem that has been so formative to me as an operator. Coming most recently from a background in product as a PM at Boston-based PatientPing, here are a few reasons why joining Underscore is so strongly aligned with my interests and longer-term career goals.


Throughout my career and education, I have always naturally gravitated towards building communities. From starting organizations in high school to organizing residential communities in college to starting SHIFT and, most recently, building/growing healthcare communities at PatientPing, community-building has always been the heart of what I truly love doing — connecting people.

At Underscore, I’ll be able to amplify and pursue this passion to its fullest: not only as a venture capitalist, but at a firm that makes community-building one of its strongest and differentiated characteristics. Underscore’s Core Community and intentional Core Syndicate model offers a compelling invitation for its community members to have an equal seat at the table with founders and venture capitalist alike. Moreover, the opportunity to grow and build new entrepreneurial communities from the ground-up is uniquely exciting to me. Having started Path to Product to serve aspiring + early-stage product managers, I’m excited to support PMs, while at Underscore, by building infrastructure to foster entrepreneurial traits that I believe are shared by all PMs. Building on past experiences at the intersection of academia and industry as a student-entrepreneur at Greylock X and Kleiner Perkins FellowI look forward to enabling entrepreneurship at the cutting edge of academia here in Boston.

People > Process

If the way that Underscore invests in candidates during their hiring process is a reflection of how they invest in companies, I couldn’t be happier to join a firm that actively reflects a people-first ethos. Throughout the interview process, I was encouraged to help shape and define the role vs. feeling like I had to contort myself to fit into a predefined mold. And from the moment I walked in the Underscore office, I could sense the team’s entrepreneurial nature — a fast-paced undercurrent that invites ambiguity and self-starters. Echoing Lily, it truly feels like Underscore is a startup supporting startups:

It’s builders supporting builders, and reimagining the VC model in the process.

With each and every conversation with the Underscore team, EIRs, portfolio companies, I got increasingly excited about joining a team that I felt like I had subconsciously known and worked with all along. It became increasingly apparent to me that what Underscore valued above all else was people. From fielding their interview questions, shadowing meetings with founders, and joining in debrief syncs, every conversation revolved around people — their superpower, their why, their story, and their uniquely differentiated worldview.

Broad vs. Deep

As I pressure-tested my own emerging interests outside of my background in healthtech with fascinating thought exercises in VR/AR and the music industry, I became more and more excited about the opportunity at Underscore to build breadth outside of my depth in healthcare. I loved the intellectual reframe of thinking broadly about many spaces and zooming out as an investor to think broadly about net-new technologies and industries.

Past experiences in HCI research and finding product-market fit in network-based B2B/B2B2C settings have given me strong interests in meeting with entrepreneurs working on frontiers of human-computer interaction(AR/VR, IoT, speech-enabled/autonomous interfaces, etc…) and network-oriented enterprise businesses (community enablement, e-commerce, network effect marketplaces, etc…). But first and foremost, I’m joining Underscore to support and enable amazing founders.

If you’re working on something new, want to get plugged into the Underscore community, or just swap thoughts about technology and product — I’m your guy! Feel free to connect with me or reach out if I can ever be helpful to you — sherman@underscore.vc — and I’d love to find time to chat 🙂