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 the outcome, and how he's using Claude and AI to manage 30+ enterprise accounts at once.

He also breaks down why AI native law firms backed by Y Combinator are coming for Big Law, and why the billing model that's sustained the industry for decades is already starting to crack.

If you're early in your sales career, building GTM at a LegalTech startup, or just trying to figure out how to sell complex AI software to process-heavy enterprise buyers, this one's worth your time.

🎙️ Taking LegalTech To Market with Theo Cox, Founding GTM at Wexler.

Chapters:

01:04 - JP Morgan, a dating app, and ending up in LegalTech03:37 - How to bounce back from career setbacks without losing momentum05:08 - Why Theo was thinking about AI before most people had heard of it07:14 - Finding Juro on AngelList and joining early stage LegalTech10:17 - What selling at Juro taught him about tool fatigue and trust11:19 - How enterprise sales at Wexler is completely different from SMB13:18 - The million dollar question: how do you sell AI to firms that bill by the hour?16:14 - Joining Wexler as one of the first GTM hires — what he built first20:00 - What a sales cycle actually looks like selling into Clifford Chance and HSF21:50 - How Theo uses Claude Cowork to manage 30+ accounts without dropping the ball24:31 - The most surprising thing AI surfaced from his sales calls26:11 - One piece of advice for his earlier self

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 To Market dropping tomorrow. 🎙️

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 To Market dropping tomorrow. 🎙️

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 building with the AI legal front door.

He also gets honest about why saying "we don't have that yet" closes more deals than saying yes to everything, and what savvy buyers are quietly scoring you on before they ever sign.

If you're selling enterprise software into legal, thinking about joining an early stage LegalTech company, or building a go-to-market team from scratch, this one has the blueprint.

🎙️ Taking LegalTech To Market with Dave Moore, Director of Enterprise Sales at Checkbox.

Chapters:

00:00 - Intro: From zero US customers to $23M raised00:47 - How Dave accidentally ended up in LegalTech02:06 - Why he left enterprise platforms for an early stage startup05:05 - Gut feeling vs. strategy when choosing a company to join07:18 - Opening a market from nothing — what the first six months really looked like10:17 - Why clients buy from Checkbox when the market has plenty of good software13:30 - How to earn trust from a buyer who's been burned before16:01 - What in-house legal teams actually want that most go-to-market teams get wrong18:59 - Is enterprise LegalTech sales really that different from standard SaaS?20:41 - What Checkbox needs to achieve in the next 12 months to become category leader23:10 - What nobody tells you before you take a job in LegalTech sales

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 most rigorous sales process he's ever run is the one he's running today.

He also gets honest about joining an industry he knew nothing about, what it actually takes to hire great AEs at Series A, and why the product you see today is always the worst it'll ever be.

If you're building a go-to-market team in LegalTech or thinking about making a big industry leap , this one's worth your time.

🎙️ Taking LegalTech To Market with Ryan Fitzpatrick, Sales Director at Orbital.

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 on Taking LegalTech To Market. 🎙️

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 brutally honest about what 23 acquisitions teach you about sales teams, why not every dollar is worth chasing, how to cut through the AI noise when you're competing against companies closing seven-figure deals in a single week, and the one trait he looks for above everything else when hiring sellers.

He also shares the mistake he made on day two at Lupl, and why he'd do it differently.

This is Taking LegalTech To Market with Abhijat Saraswat. Available Now. 🎙️

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 tomorrow. 🎙️

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 hitting eight-figure ARR, all while going through Y Combinator and building a global team across London, New York, and Munich.

We get into the real mechanics of how they built their go-to-market flywheel, why speed is the single biggest competitive advantage in AI, and what it actually takes to hire top 1% talent for a company growing this fast.

If you're in LegalTech, building a startup, or just want to understand how AI is reshaping one of the most technical corners of the legal world, this one's for you.