Unusual Ventures: The enterprise VC that embeds operators inside its startups

Most venture firms promise to be hands-on. Unusual Ventures took the promise literally: its founder services programme embeds full-time operators inside portfolio companies for months at a time, working on product-market fit as an inside team member rather than a distant adviser. "It's the difference between me giving you a course on sleep training and being a night nurse," managing director John Vrionis told TechCrunch when the firm closed its third fund, worth $485 million, in 2022.

The Menlo Park-based firm was founded in 2018 by Vrionis, previously an investor at Lightspeed Venture Partners, and Jyoti Bansal, the serial entrepreneur who founded AppDynamics — which Cisco acquired for $3.7 billion — and later Harness, which announced a $230 million Series D at a $3.7 billion valuation. Bansal still sits on a handful of Unusual boards and oversees the founder services programme. The partnership also includes general partners Lars Albright, Sandhya Hegde and Wei Lien Dang, plus operating partner Scott Schwarzoff.

Unusual invests exclusively in enterprise software at seed and Series A: developer tools, cybersecurity, cloud infrastructure and AI applications. Its thesis is bluntly stated on its homepage — "Turning product-market fit from improbable to inevitable" — and it has put real scaffolding behind the slogan. The firm's Field Guide, a proprietary playbook for finding product-market fit, has crossed 1 million views, and its portfolio founders get access to operators who have actually built and sold large enterprise companies.

The capital backing is substantial but deliberately restrained. Unusual raised a $425 million second fund in late 2019, then stepped up only modestly to the $485 million Fund III in May 2022 — intentionally, says Vrionis, rather than chasing the multi-billion-dollar fund sizes common in enterprise venture. Check sizes generally run in the low millions, and the firm leads or co-leads seed and Series A rounds for founders building infrastructure, security and AI companies.

Notable portfolio companies featured by the firm include Harness, Traceable, Socket, Chalk, Databento, Railway, Fal and Resolve AI. For founders selling to the enterprise, the firm's value proposition is unusually concrete: a partner who has navigated billion-dollar exits in the exact category you operate in, sitting on your board and embedded in your company.