With $112M Fund, Glasswing Looks to Drive East Coast A.I. Startups

In a sea of emerging tech venture funds, Glasswing Ventures is trying to stand out. The Boston firm announced today it has closed its debut investment fund at $112 million.

That’s bigger than the “micro-VC” funds of the past decade, but much smaller than the mega-funds (often in the billion-dollar range) that have been raised recently by big players like General Catalyst Partners, Norwest Venture Partners, and New Enterprise Associates.

And that’s just fine with the Glasswing team (pictured), who see themselves as filling a need up and down the East Coast—namely, investing in seed-stage startups that are applying artificial intelligence technologies in enterprise software and cybersecurity.

Not that there aren’t plenty of investors working in these competitive areas. Glasswing joins the ranks of other recently formed Boston firms that invest in tech startups at an early stage, such as G20 Ventures, Pillar Companies, Underscore VC, and The Engine. Other local VC firms currently raising debut funds include Converge and One Way Ventures.

Glasswing stands out for being majority women-led, with managing partner Rudina Seseri and managing director Sarah Fay at the helm, together with managing partner Rick Grinnell. Seseri and Grinnell were previously at Fairhaven Capital, where they invested in companies such as EqualLogic, Resilient Systems, and Jibo; Fay was formerly CEO of Aegis Media North America, a media and marketing communications company. (It’s worth noting that Converge is also women-led, with Maia Heymann and Nilanjana Bhowmik as the founders.)

Seseri says her firm is “singularly focused on [startup] founders and how we can be of value to them.” She talks about “becoming an extension to their teams” and helping startups with their go-to market strategy, recruiting talent, and securing early customers.

Glasswing has made five seed investments, of which the firm has announced three—Talla and Allure Security in the Boston area, and Terbium Labs, a cybersecurity startup based in Baltimore. Several other deals are in the works, Seseri says, but she declined to share details.

As she explains, Glasswing looks to invest about $1.5 million to $3 million in each seed funding round, making up about half the total round. The firm also makes “pre-seed” investments of a few hundred thousand dollars each, she says. All told, Glasswing is targeting about 15 to 20 seed investments from its current fund, and a greater number of pre-seeds.

It took Glasswing a little over 18 months to raise its fund, Seseri says, from a mix of foundation and university endowments, pension funds, and family offices. Now, the firm has to prove it has the right approach to A.I. investing.

Seseri seems confident. She says her team is “looking at A.I. as a driving factor and an underlying factor… and from an end-market point of view.” In terms of interesting startup markets, she mentions sales tech, human resources, the future of work, and broad ideas about “data decentralization around the Web.”

I took her investment thesis to mean Glasswing is targeting entrepreneurs and companies that are using machine learning and sophisticated data approaches to deliver enterprise software that’s more secure and intelligent than what’s currently available. It won’t be easy—but that’s why the startup ecosystem is clamoring for more smart investors.

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