Welcome to our monthly newsletter, Scooped.
Each month, co-founders Tom Dreyfus and Sam Flynn curate the latest news in legaltech and AI, and share what teams are creating on Josef.
Have a read and don’t forget to subscribe!
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Summer has arrived (well, for some of us), which we hope means you’re reading this by a beach or pool! In this edition: Sam dropped by adidas HQ in Amsterdam to catch up with General Counsel Katherine Roseveare, we published our report on The Future of Contracting from CLOC in Chicago, and we hosted our APAC Josefites in Melbourne. Outside Josef land, we urge you to steer clear of the AI doorman fallacy, and to listen to a thought leader not usually doing the rounds on LinkedIn: the Pope!
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It’s “infobesity”, if you ask Katherine Roseveare.
Chatting with Sam about adidas‘ work with Josef over the past year, the General Counsel put it like this: “Lawyers love producing documents, policies, frameworks. But nobody wants to read those anymore.”
So how do you counsel 65,000+ people when nobody has time to engage? You turn legal and compliance knowledge into AI tools that meet people where they work. The unexpected bonus? People start asking the questions they’d previously be “too embarrassed to ask.”
Read our recap or listen on:
How do you adopt new tech when the market will look completely different in a year’s time? In May, we put that question to 25 in-house leaders at CGI in Chicago, and this month we published a report with Kimberly Bell and Jenn McCarron on what we learned.
The consensus? Don’t lock in. The Future of Contracting digs into how leading legal ops teams are building tech stacks that are best-in-class, interoperable, and most importantly, interchangeable. Featuring insights from Canva, Nutanix, DHL, Ford, L’Oréal and more.
A hotel decides the doorman just opens doors, so they replace him with a sensor, only to later notice his role went further: greeting guests, hailing taxis, keeping the place safe.
Sound familiar? Gediminas Lipnickas seems to think so, writing how plenty of companies are making the same mistake with AI, pointing to examples from Banks that had to rehire, and Taco Bell which is now rethinking its drive-through.
From what we’ve seen, the best AI rollouts are never about replacing human thought and connection, but carving out space to apply those skills where they’re needed most.
That’s the line that stuck with Sam most from Pope Leo XIV’s encyclical on AI a few weeks ago.
He doesn’t take the easy exits. AI isn’t “just a tool”, and the answer doesn’t simply rest on more guardrails. Instead, he reaches for the Biblical examples of Babel (efficiency at the cost of dignity) and Nehemiah (rebuilding the society before the walls of the destroyed Temple). The question he leaves us with: “What are we building?” If we don’t seek out more humanity, we’ll “have more” without “being more”.
A handful of Josefites came together to hang out with a VIP guest in Melbourne this month: Ben Armstrong, one of the first investors to back Josef back in 2018.
Ben sat down with the team to share what he looks for in the companies he backs (healthy customers, mostly), and why legaltech went from a VC backwater to one of the most exciting markets around. Tom’s personal takeaway? The first person who believes in you matters more than almost anything.
So, what’re you waiting for? Go find yours!
