Rudina Seseri can spot an “AI-native” company from a mile away.
Before ChatGPT sounded the starting gun on the artificial intelligence revolution, Seseri, the cofounder and managing partner of Glasswing Ventures, was already writing the first checks to machine-learning startups, arguing that data-hungry algorithms would define the next era of software.
In the current hype cycle, every tech startup is dedicating resources to AI. But that doesn’t mean the algorithms are doing the heavy lifting everywhere. Some teams grab an off-the-shelf model, wedge it into an otherwise ordinary software stack, and call it innovation.
AI-native companies follow a fundamentally different blueprint. Their core architecture is designed around machine intelligence from day one.
Founders say that Seseri on a cap table has become code for “the real deal.”
“Partnering with Glasswing instantly signals credibility,” Philippe Rival, whose risk management platform Enlaye received an investment from the firm, said. “Everyone knows that if Glasswing is involved, it’s a real AI-native company.”
Seseri has spent the better part of two decades investing and operating at the high-tech frontier. Before venture capital, Seseri was a senior manager in corporate development at Microsoft, where she led several acquisitions.
She’s backed fast-rising enterprise-tech plays, including in Reprise, whose interactive demo platform drew a $62 million Series B in 2022; Verusen, a materials intelligence suite that raised $25 million that same year; and Basetwo, which blends physics with AI to tune drug- and chemical-production lines and secured an $11 million Series A this January.
Since 2018, the firm’s assets have swelled to over $270 million across two funds. It’s going back out for more; an SEC filing shows that Glasswing plans to raise a third fund. Seseri declined to comment on the fundraise.
Seseri has stayed ahead of the curve by being the first to identify founders poised to disrupt enterprises from logistics to Big Pharma. Glasswing said last year that it was the first institutional investor in all of its portfolio companies.
Founders have no shortage of investors to choose from. Seseri said that when a founder has multiple term sheets, she wins deals because of her expertise.
“She is on the bleeding edge of everything with AI,” Scott Matthews, the CEO of Verusen, said. Its cloud platform uses advanced data science and AI to clean, unify, and analyze the messy materials data in many manufacturers’ enterprise systems.
Fifteen years ago, Seseri was leading deals as a software investor at Fairhaven Capital, an early entrant in Boston’s venture scene. One day, she waved Rick Grinnell, her mentor and one of the firm’s founders, over to her desk.
She had noticed something new about the companies she was meeting. With the increased availability of big data and ever-more powerful compute, founders were applying deep learning to tackle complex problems for businesses.
“There’s something happening and it’s not big data,” Seseri told Grinnell. “I’m telling you something has changed.”
He nudged Seseri to dig deeper.
In 2016, Seseri and Grinnell left Fairhaven to start Glasswing, centered on what she called a “seismic shift” in technology. Forty percent of Fairhaven’s limited partners signed on to back their initial fund. In 2022, the firm closed its second, slightly larger fund with $158 million.
Perched on Newbury Street in Boston, Glasswing’s offices function as a second home for its founders. Matthews and Verusen’s founder, Paul Noble, recently sat with Seseri for two hours in a glass conference room, contemplating the company’s architecture and future.
Seseri is in the office five days a week. She spends hours on the phone, working her network to help founders hire, raise a round, or close a customer. That support often arrives before Glasswing even issues a term sheet.
Seseri’s track record puts her on speed dial for founders building at the frontier.
“But at the end of the day,” Seseri said, “we win deals because of how our founders support us and what they share with other founders.”
