Taking LegalTech To Market
Taking Legal Tech To Market is a podcast where legal tech founders and revenue leaders share the real go-to-market playbooks behind successful legal technology companies. Each episode explores how these companies win, covering sales strategy, market positioning, go-to-market hiring, and lessons learned while scaling. Hosted by Paul Church, founder of Talent & Growth and a specialist recruiter for legal tech go-to-market talent. New episodes are released every week.
Episodes
How To Sell When Every Buyer Has Seen 50 AI Tools Already | Dan Gallipeau | Courtroom
Dan Gallipeau spent 41 years as a trial consultant, over a thousand cases, standing next to some of the best litigators in the country. Last year he co-founded Courtroom, AI software that simulates jury decision-making so trial teams can get juror input months before they ever walk into a courtroom.Two years in: Am Law 100 firms and Fortune 100 companies in the pipeline, with major law firms activ
Everyone wants to be client number two or three | Dan Gallipeau | Chief Strategy Officer: Courtroom
Nobody wants to be the first law firm to sign. Dan Gallipeau from Courtroom on how credibility builds client by client, why their data policy has won deals, and the 9pm-before-court test every LegalTech product has to pass.Full episode out tomorrow. Subscribe so you don't miss it.
100 Clients and Zero Marketing Spend | Luke Versweyveld | Co-Founder & CEO: Virgil
Luke Versweyveld launched Virgil in August 2024 with a co-founder from Answer AI and a mandate from Eric Rees, author of Incorruptible, to build the legal and back office infrastructure that the governance framework needed to actually work in practice.Two years in: a hundred clients, a wait list, zero marketing spend. The growth engine is entirely word of mouth, split roughly 50/50 between their o
Are You Sure You Can't Get Us In Any Earlier?
Luke Versweyveld didn't set out to hold off on marketing. Virgil just kept filling up through word of mouth before he ever needed it.Two years in: a hundred clients, a wait list, and a growth model built entirely on the quality of what they deliver. Luke assumed wait lists couldn't be done in legal, if a law firm won't help you today, you find one that will. Virgil proved that wrong.In
We Were Selling Efficiency. They Were Selling Hours. Something Had To Break | Matthew Basile | CEO: Naya Law
Matthew Basile built Naya while billing two thousand hours a year as a senior associate at a large law firm. He licensed the platform back to his own employer, sold it to other firms, became a partner, and eventually ran into the wall that every LegalTech founder eventually hits when selling into a billable hour model: every hour you cut is revenue someone else in the building used to earn.In this
$40K to Close a $2M Loan. That's When We Threw Out the Model.
Matt was a senior associate at a large law firm billing two thousand hours a year. He was also selling that same firm his own software. Every time it worked, someone in the building lost revenue. That tension doesn't resolve. It compounds.In this trailer: why signing a 400-lawyer firm isn't the contract you think it is, why $40K to close a $2M loan forced him to throw out the model entirel
How To Create Customers That Create More Customers | Jacob Adberstein | Co-Founder/CEO: Reflekt Legal
Jacob Adberstein came from NASA. His brother came from cybersecurity. Neither had a legal background. That turned out to be exactly the right perspective to see a problem the industry had stopped noticing, law firms are losing clients at the intake stage before a lawyer ever picks up the phone.Reflekt Legal builds AI employees that handle reception and intake across voice, email, and SMS. The prod
You Can Vibe Code a Demo. You Can't Vibe Code Trust.
Lawyers are the hardest buyers in any market. They've been overcharged by every vendor they've ever dealt with, and they remember it. Jacob Adberstein built Reflekt Legal knowing that, and built his entire GTM motion around earning trust rather than closing deals.In this trailer: why he tells customers not to buy when buying isn't right for them, why he'd rather be last in an evalu
Why I Always Tell My Customers To Try My Competitors First | Maryam Salehijam | Founder: Andarzi
Maryam Salehijam walked out of a Stanford Law visiting research position into LegalTech sales, with no legal background, no network, and a PhD in something completely different. That outsider perspective is exactly why she sees things most people in this market miss.In this episode Maryam breaks down the full picture: why the objection has shifted from "we don't trust AI" to "we
You Didn't Even Read the Email Your AI Sent to Me.
Maryam Salehijam is ex CRO at Junior, AI patent drafting. She's selling AI to lawyers. And she's also the person on the other side of your outbound sequence, watching salespeople ask questions that were already answered in the AI-generated email they clearly never read.In this trailer: why she deliberately wants to be last in every evaluation, why she tells buyers exactly who her competito
The Hidden Cost of Staying When Your Industry Is About To Break | Nathan & Michael | Landfall IP
Nathan Mutter and Michael Drapkin were top outside counsel at Qualcomm, Micron, and Salesforce. When the ChatGPT moment hit, they didn't wait to see what would happen to their industry. They walked away from the most profitable position in the market and built Landfall IP, an AI native patent law firm, from scratch.In this episode they break down the full picture: why they built a law firm rat
They Left Qualcomm and Salesforce as Outside Counsel to Build This. Here's Why.
Profits per partner go up every year. That's exactly why most law firms won't change.Nathan Mutter and Michael Drapkin were top outside counsel at Qualcomm, Micron, and Salesforce. When they saw what AI was going to do to their industry, they didn't wait. They walked away and built Landfall IP, an AI native law firm from the ground up.In this trailer: the Malcolm Gladwell risk reframe
Why Free Pilots Are Killing Your Conversion Rate | Eimear McCann | Commercial Director: TrialView
First demo: four years ago. Closed: last week. And that's not the exception, that's what selling into large law firms actually looks like when you're nine years in and still showing up.Eimear McCann is Commercial Director at TrialView, an AI disputes platform built for the full lifecycle of litigation. She joined in 2021 when the incumbent was so embedded that buyers genuinely thought
First Demo 4 Years Ago. Closed Last Week. The TrialView GTM Story.
The first demo was four years ago. The deal closed last week. That's not a failure, that's what selling into large law firms actually looks like.Eimear McCann has been selling into litigation technology for nine years. In this trailer she covers the pilot mistakes that kill conversion rates, why free trials are worse than charged ones, why outbound email is over, and why headline sponsorsh
Why Word of Mouth Is Still The Strongest GTM Motion In Legal AI | Bryan Lee | CEO: Ruli AI
Selling to in-house legal teams is harder than selling to law firms. They don't generate revenue, budgets are tighter, and teams are smaller. Bryan Lee built Ruli AI into that headwind anyway, and one early customer saved $850,000 in a year by replacing outside counsel spend with a 3-person in-house team using the platform.In this episode Bryan breaks down the full picture: why word of mouth i
She Saved $850K in a Year. That's How We Sell to In-House Legal Now.
Selling to in-house legal teams is harder than selling to law firms. They don't generate revenue, which means every purchase needs a finance team sign-off.Bryan Lee built Ruli AI into that headwind anyway. One early customer saved $850,000 in a year by replacing outside counsel spend. That became the sales story. Not features. Not efficiency. A number the finance team couldn't argue with.I
THE £1M DEAL TRAP | Nick Morgan: Chief Client and Commercial Officer at Jalubro
Nick Morgan is number one salesperson in the door at Jalubro. No sales team behind him. No marketing function. No office. Just a 10-year-old professional services business pivoting into software, and a governance product that nobody in the market is talking about yet.In this episode Nick breaks down what it actually looks like to build a GTM motion from scratch with limited resource. Why he's
Season 2: Episode 1 (Trailer)
The minute a contact says "I'll manage this myself, don't worry", that's not reassurance. That's a giant alarm bell.Nick Morgan has spent a decade inside enterprise legal technology, most recently as Chief Client & Commercial Officer at Jalubro. He's seen exactly how deals die, how governance gaps become business risks, and why the AI adoption conversation in lega
Taking LegalTech to Market | Season 2 Official Teaser
First demo: 4 years ago. Closed: last week.6 founders and GTM leaders talking straight to camera about what selling, building, and scaling LegalTech actually looks like in 2026. No script. No polish. Just the honest version.Hosted by Paul Church, with guests:Jacob Adberstein · Reflekt LegalNathan Mutter & Michael Drapkin · Landfall IPMaryam Salehijam · JuniorEimear McCann · TrialViewBryan Lee
SEASON ONE RECAP
Ten conversations. Ten people who are actually doing it right now.Season 1 of Taking Legal Tech to Market features founders and GTM leaders who are building, selling, and scaling LegalTech businesses in real time. No theory. No retrospectives. The real playbooks, the real mistakes, and the real roadmaps.Chris Parsonson on why speed is the only advantage a startup has. Abhijat Saraswat on why not e
His First Pilot Sold One License. His Pilots Now Convert at 95% | Nathan Killick | GTM Lead: Definely
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
Episode 10 (Trailer)
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 need
No Demo. No Sales Call. No Salesperson. Here's The GTM Model | Nick Holzherr | Founder: GitLaw
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 structured
Episode 9 (Trailer)
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 questio
Candle AI - Pivots, Pricing and The Conference Circuit | Sujith Jose | Founder: Candle AI
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
Episode 8 (Trailer)
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 o
The Hidden Cost Of Building LegalTech Before You Validate The Buyer
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, Al
Episode 7 (Trailer)
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 Market
Why The GC Is The Hardest Person In Any Building To Sell To | Andrew Ferguson | Wordsmith AI
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 a
Episode 6 (Trailer)
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
The Truth About AI Adoption In Legal Nobody Admits
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 th
Episode 5 (Trailer)
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
Why Trust Beats Features In Every LegalTech Deal | David Moore | Enterprise Sales Director: Checkbox
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 build
Episode 4 (Trailer)
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. 🎙️
Adapt or Die. Why Property Law Is Finally Ready For AI | Ryan Fitzpatrick | Sales Director-Orbital
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 m
Episode 3 (Trailer)
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
Why Rejection Is Higher on Your Best Days | Abhijat Saraswat
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 brutall
(Episode 2 Trailer)
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 tomorro
When the product is the pitch: $3.5M ARR without a sales team, $13M ARR within two years | Chris Parsonson
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 hit
(Episode 1 Trailer)
''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 actual
