VC Spotlight: Jackson Square Ventures
They say capital doesn't sweat. Jackson Square Ventures makes you sweat with conviction before they write the check. In 2011, four partners left Sigma Partners to build something with a pulse, an all‑partner VC that bets on substance over sizzle. Greg Gretsch, Pete Solvik, Bob Spinner, Josh Breinlinger, they didn't just trade suits for spreadsheets. These are operators who built and exited real businesses before they picked up the term "Series A." No juniors. Just board‑room muscle from day one.
Greg Gretsch came from a string of startups, Connectify, Vicarious, GiftONE, and steered Responsys into Oracle's orbit. Pete Solvik ran IT at Cisco and Apple before he co‑piloted enterprise software deals like DocuSign. Bob Spinner brought SaaS chops from Extensity, Clarify, and Sybase. And Josh Breinlinger, who architected oDesk (now Upwork), advocates anti‑hype investing with battlefield wit. They even brought on Dan Preston as Venture Partner, ex‑Metromile CEO, and John Otterson to run ops and investor relations. This isn't a fund with hired guns. It's the same players, every time.
The thesis is simple: find the troughs we forgot, not the peaks investors hustle to chase. They dived into "boring" markets like healthcare delivery, back office infrastructure, fintech plumbing, places where incumbents sleep and fundamentals matter. That trough‑of‑hype mindset picked winners like DocuSign, IPO'd in 2018 at over $4 billion. Upwork did the same. Strava, OfferUp, Seismic, Alto Pharmacy, all built on the kind of grit and discipline that shows up late, stays long.
Their third fund closed at $193 million in October 2019, 30 percent over target. That's not hype. That's reputation. They underwrite low‑beta portfolios: roughly 20 percent loss rate while the rest build into unicorns. That's math you can bank on, not buzz you can't.
But here's what gets me: they don't just write checks. They sit on boards, open Rolodexes, lobby accounts, help hire what you can't, launch go-to-market engines. They host the JSV Book Club, where no fluff passes, and quarterly salons that feel more like strategy camp than cocktail hour. That operator DNA ripples through every founder they back: domain experts, quietly confident, obsessed with metrics, accountable to customers and culture.
Now JSV portfolio companies are hiring: engineering, product, GTM. Want a job with capital that's active, not passive? A team that co‑builds, not just advises? Explore career pages on the link in the comment. Get your foot in the door with startups built on operator fuel.
DocuSign: https://careers.docusign.com/
Upwork: https://www.upwork.com/careers
Strava: https://www.strava.com/careers
OfferUp: https://about.offerup.com/careers
Seismic: https://www.seismic.com/careers/
Alto Pharmacy: https://www.alto.com/careers
Jackson Square Ventures doesn't sit on hype. They sprint through the grind, unshakeable in troughs, hungry for fundamentals. If you want to be seen, be built, be deployable, stop chasing noise. Go where the silence still echoes with opportunity.
Follow this firm. Study their founders. Track their plays.
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