Startup Boston Week Sneak Peak: James Massaquoi of Glasswing Ventures

James Massaquoi is part of the investment team at Boston-based Glasswing Ventures, an early-stage venture capital firm investing in AI-native and frontier tech companies transforming enterprise B2B and cybersecurity markets. Glasswing pairs deep technical expertise with a strong commitment to the Boston startup ecosystem, and Massaquoi works across sectors to back companies solving real, high-impact business problems with defensible moats and high potential to scale.

James will share his perspective on evaluating young companies as a speaker at Startup Boston Week 2025. Massaquoi is part of the panel, Gut Feel or Game Plan? Mastering Early-Stage Due Diligence (Friday, September 12, 11:00 am–12:00 pm EDT), which will walk attendees through building a repeatable framework for assessing early-stage startups – from evaluating founders and product-market fit to analyzing financials, technical capabilities, and market potential. The session is aimed at new fund managers, angel investors, and founders who want to better understand the investor mindset.

We spoke with Massaquoi ahead of the event about how Glasswing defines “frontier tech,” what’s next for early-stage investing, and why Boston’s startup ecosystem is high on his list.

Startup Boston: Let’s start with Glasswing Ventures. Your site says you focus on frontier tech. That’s a broad term these days, so I’m curious, how do you define it?

James Massaquoi: When we say frontier tech, we refer to the cutting edge of technology. Tech is rapidly evolving all the time, and since its inception, Glasswing has made a concerted effort to remain “on the frontier” of new technology. When our Managing Partners, Rudina Seseri and Rick Grinnell, founded the firm in 2016, frontier tech referred to technologies like AI, human-computer interaction, and quantum computing – products that reimagine enterprise B2B and cybersecurity markets and deliver previously unattainable levels of ROI. Today, the notion of providing meaningful enterprise impact continues to drive our investments and the tech we are focused on.

SB: In terms of AI, what sets Glasswing apart in such a crowded space?

JM: Three things. First, we’ve been doing this since 2016 – well before the AI hype. We didn’t have to catch up; AI fluency is embedded in our DNA. Second, the team has real-world experience building and scaling AI companies. Rick began his career as an engineer at PictureTel, then transitioned into product marketing and venture capital. Our Partner, Kleida Martiro, has managed data science and product teams, while our other Senior Investment Associate, Zach Jaffe, served as the Director of GTM Strategy and Operations for Turbonomic (acquired by IBM) before transitioning into venture capital. Third, we take a thesis-driven approach to investments. We don’t just read white papers and invest accordingly, but we do engage deeply with technical literature to inform our theses.

We’re also lucky to have Vlad Sejnoha, the former CTO of Nuance Communications, as a partner. He brings decades of experience in speech and language tech, including work that helped lay the groundwork for Siri, to the firm. That kind of foundational knowledge is invaluable when evaluating true AI-native products versus wrapper technologies.

SB: How did you personally get into VC?

JM: I grew up in Delaware, went to the University of Delaware, and was always drawn to startups and education policy. My path wound through early edtech gigs, a medical device startup, and eventually, I co-founded a company using lidar to help first responders navigate buildings. 

When Covid threw a wrench in our go-to-market plans, I joined Amazon.com on the retail side, working with beauty brands like L’Oréal and Elf. That experience gave me exposure to supply chain, marketing, and customer data at scale. After that, I joined Osage Venture Partners, where I spent nearly three years investing in enterprise B2B startups – especially those at the intersection of AI, SaaS, and cybersecurity. There, I led my first AI agent deal and realized this was the space where I wanted to go deep. When I found out Glasswing was hiring, I jumped at the chance.

SB: What themes are you paying the most attention to heading into 2026?

JM: At a high level, we’re still focused on AI-native companies: those with proprietary data, defensible moats, and real workflow insight. I’m especially excited about AI agents and their ability to compartmentalize tasks and reduce hallucinations. Instead of one large model generating a full output in one go, agents break down tasks into steps, like a swarm of small workers each focused on a single job, with guidance from a higher-level agent. Agents improve reliability and accuracy, which is crucial in high-stakes sectors like manufacturing, healthcare, and finance, where AI systems must meet stringent regulatory standards, integrate seamlessly within existing operational workflows, and achieve near-perfect performance to avoid costly errors, compliance violations, or safety breaches.

The infrastructure for agents is also maturing. New protocols are making it easier to feed non-standard data into LLMs. That opens the door for AI to operate in traditionally risk-averse industries, like pharma, chemicals, or compliance-heavy environments, where you need human-level accuracy. One example from our portfolio is Basetwo, which helps chemical engineers streamline processes without compromising safety.

Another is Asepha, which automates workflows for both pharmacies and pharmacy benefit managers (PBMs). With accuracy now at or above human levels in some tasks, pharmacists and PBM teams can delegate time-consuming but routine checks to AI, reserving their time for final review.

SB: And what are you hoping to get across at Startup Boston Week?

JM: Honestly, I just want to meet people. I’m still new-ish to Boston – I have been here just over a year – and I’m blown away by how smart and collaborative this ecosystem is. 

At Startup Boston Week, I’ll talk a bit about what we look for in investments – both vertical and horizontal solutions that are powered by AI or frontier tech. We back companies solving real problems: compliance pain points, complex sales workflows, and areas where automation has 10x potential.

Conclusion

From his early days in edtech and medtech to his current role investing in cutting-edge AI and frontier technologies, James Massaquoi has built a career around identifying innovations that solve complex, high-impact problems. At Glasswing Ventures, that mission means backing founders who not only have the technical expertise but also the vision and resilience to transform entire industries.

If you want to hear more of Massaquoi’s insights - and learn how to approach early-stage due diligence with both structure and intuition - join him at Startup Boston Week 2025 for Gut Feel or Game Plan? Mastering Early-Stage Due Diligence on Friday, September 12. Whether you’re an investor, a founder, or just startup-curious, it’s a chance to gain a sharper lens on what makes a young company worth the bet.

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About the author: Randall Woods is a former editor at Bloomberg News and is currently a Senior Vice President at SBS Comms, a communications agency for technology companies and startups.