Taking LegalTech To Market

Nathan Killick's first pilot at Definely converted one license. From a firm he already knew. After four months in the role. He sat with that result, mapped exactly what broke, built a repeatable process from scratch, and hit over 100% of target in his first full year. His pilot conversion rate since then? 90-95%. That turnaround didn't come from the product. Definely is a great product. It...

One license. From a firm he already knew. After four months in the role. Nathan Killick didn't spin it. He sat with the result, identified exactly what broke, and built a process so repeatable his pilot conversion rate hit 90-95%. In this trailer: why vendors kill their own deals, why copying everyone else's GTM playbook is a losing strategy, and the one question every LegalTech founder ne...

Nick Holzherr spent millions of pounds on legal fees building and selling businesses, including selling Whisk to Samsung. That experience didn't just give him a product idea. It gave him a perspective on the law firm business model that most people in legal are too close to see clearly. 80-90% of what you pay in a legal bill is overhead. AI makes that overhead free. But law firms are structure...

80-90% of your legal bill is overhead. AI makes it free. Nick Holzherr spent millions building and selling businesses, and most of it went on legal fees. That experience didn't just give him a product idea. It gave him a view of the law firm business model that most people inside it can't see. In this trailer: the pyramid that makes law firm pricing impossible to reform, the wrapper questi...

Half of every lawyer's day disappears into email. Not client work. Not billable hours. Email. And if a client doesn't hear back within 24 hours, that's already a signal of low customer satisfaction. Sujith Jose saw this from the outside. He's not a lawyer, his only experience with legal was his own immigration process. But that distance gave him a view of a problem the industry had normalized into...

Half of every lawyer's day disappears into email. If a client doesn't hear back within 24 hours, that's already a signal of failure. Sujith Jose saw this problem from the outside, and built Candle AI to fix it. Two months after his baby was born. One part-time engineer. A product that had to work fast. This is the trailer for the full episode of Taking LegalTech to Market, covering the GTM reality...

Alex has spent 300 hours interviewing 200 LegalTech founders to produce one report. What came out of it wasn't a playbook, it was a diagnosis. Most founders build something they find intellectually interesting, then discover too late that nobody is willing to pay for it. The ones who survive figure out one thing first: are you giving the buyer an undeniable reason to change? In this episode, A...

There are more than 5,000 LegalTech companies in the market right now. Most of them are blasting out cold emails, building products founders find interesting, and adding headcount on top of shaky foundations. In this trailer, Alex gets honest about why most LegalTech GTM fails before it starts, and what the companies that actually win are doing differently. New episode of Taking LegalTech To Marke...

Andrew Ferguson joined Wordsmith as one of the first GTM hires. No sales function. No playbook. Founders undercharging by a factor of 20. In this episode, Andrew breaks down how he built the go-to-market motion from scratch, segmented the team as the business scaled, and why the AI outbound wave didn't make sales easier, it made everyone start again. He also gets honest about where salespeople...

The AI outbound wave crashed. Inboxes flooded. Response rates collapsed. And yet most sales teams are still running the same motion. Andrew Ferguson walked into Wordsmith when there was no sales function, no playbook, and a product being undercharged by a factor of 20. What he built in the first year, across three market segments, through a 10x growth period, and into a US expansion, is the most h...

Theo Cox skipped university, landed on a JP Morgan trading floor, burnt out building a dating app startup, and ended up as one of the first GTM hires at Wexler , selling AI litigation software to some of the most cautious buyers in the world. In this episode, Theo gets honest about what it actually takes to sell into Magic Circle law firms, why a flashy demo means nothing if you can't deliver...

Theo went from JP Morgan to a dating app startup to selling AI litigation software to Clifford Chance and Goodwin. In this trailer, he gets honest about burning out as a first-time founder, why a flashy demo means nothing if you can't deliver the outcome, and why AI native law firms funded by Y Combinator are coming for Big Law whether they're ready or not. New episode of Taking LegalTech...

Dave Moore left the safety of enterprise platforms like MitraTech to become Checkbox's founding account executive in North America, before they'd raised a dollar in the US and with almost no customers in the region. In this episode, Dave breaks down what it actually takes to open a market from nothing, why trust beats features every time in enterprise legal sales, and what Checkbox is buil...

Dave has heard it directly from customers. And it's the thing he's most proud of. In this trailer, he gets honest about what it actually takes to build trust in LegalTech sales, why saying "we don't have that yet" beats overpromising every time, and why savvy buyers are quietly scoring you on every interaction. New episode of Taking LegalTech To Market dropping tomorrow. 🎙️

Ryan Fitzpatrick spent a decade in video tech, ran global accounts at Synthesia, and then made a move nobody saw coming, joining Orbital to sell AI software to real estate attorneys. In this episode, Ryan breaks down why he believes property law is the biggest untapped opportunity in LegalTech right now, how Orbital cracked the Magic Circle in the UK and is now scaling fast in the US, and why the...

Ryan joined a LegalTech company targeting real estate law, from outside the industry entirely. No 20 years of attorney experience. No legal background. What he brought instead: process, playbook, and a track record of building sales machines inside fast-growing companies. In this trailer, he explains why that bet paid off, and why right now is the moment to move. Full episode out tomorrow at noon...

Abhijat Saraswat was called to the bar, looked at the legal profession from the inside, and decided he'd rather sell to lawyers than be one. That instinct led to employee number three at Xref, growing it from near zero to seven figures and through an acquisition. Then 23 M&A transactions at Litera. Then joining Lupl to rebuild their go-to-market from scratch. In this episode, Ab gets bruta...

Not every dollar is equal. The effort it takes to close a deal might not be worth it in the long run, and most salespeople never figure that out. In this episode, a LegalTech sales leader gets brutally honest about hustle culture, what rejection really means, and the one personality trait he looks for above everything else when hiring. This is Taking LegalTech To Market. New episode dropping tomor...

Chris Parsonson co-founded Solve Intelligence with his brother and a fellow UCL PhD researcher, and his girlfriend just happened to be a patent attorney. That combination of insider access and AI expertise led to one of the most interesting LegalTech origin stories you'll hear. In this episode, Chris breaks down how Solve went from writing its first line of code to serving 400+ IP teams and hi...

''Speed really is the most important thing in a startup, and in the world of AI, things move incredibly quickly." Chris Parsonson co-founded Solve Intelligence straight out of his PhD at UCL. Two years later: 400+ IP teams, eight-figure ARR, offices in London, New York, and Munich. In this episode, he breaks down how they built their go-to-market flywheel from cold outbound, what Y Combinator actu...