Some law firms bill you for blinking. Others bill you for breathing. Covenant? They bill for clarity, and they move like an AI-powered freight train through the molasses of private market legal sludge.
Let’s talk about what just dropped: Covenant just secured a $4M seed round, led by Flybridge Capital Partners, with a strong signal from Neil Barsky, the ex-hedge fund manager, ex-WSJ journalist, ex-everything who still somehow lands on the right side of every bet. And the bet here? It’s on Jen Berrent and Richard Perris, two former legal war generals turned founders, who traded in their firm badges and C-suite titles for something sharper: a human-AI hybrid that eats LPAs for breakfast and side letters for sport.
Jen Berrent, ex-CLO and COO of WeWork, former WilmerHale partner, Wharton/NYU double threat. Richard Perris, former GC at CVC Capital Partners with a resume that reads like a private equity opera in five acts. Together, they’re building Covenant not as a law firm that uses AI, but as an AI-native law firm with law-firm grade muscle. That distinction matters. One is lipstick on a pig. The other is a whole new species.
Covenant is targeting the legal mess that’s been chewing up allocators for decades: LPAs, MFN elections, NDAs, all the alphabet soup you pray your external counsel gets right before you wire $200 million. They built a multimodel AI system (three models minimum) backed by human-in-the-loop review that promises 100% accuracy tolerance. That’s not marketing bravado. That’s 45 institutional clients, SOC2 Type II certs, and zero data retention policies wrapped in a turbocharged dashboard that lets LPs compare term sheets like it’s fantasy football for allocators.
Their LPA Review Tool clocks in at $900 per doc, 15% of the time, 10% of the cost of Big Law. And their new MFN Election Tool? It launched the same day the funding hit. Coincidence? Nope. That’s product-led execution in motion.
Flybridge General Partner Jesse Middleton backed this before there was product, revenue, or a single line of code, just a conviction that Covenant was going to own the private funds legal stack by 2025. Middleton also happened to be a WeWork OG. So when he says he sees something familiar in Jen Berrent, it’s not nostalgia, it’s pattern recognition.
The takeaway? Legal doesn’t have to be bloated, slow, or prohibitively expensive. Not when your firm is part law practice, part machine, and all killer, no filler. Covenant isn’t nibbling around the edges of legal tech. They’re going for the jugular.
