Taking LegalTech To Market

Paul Church

Taking Legal Tech To Market is the podcast where Legal Tech founders and revenue leaders break down the real go-to-market playbooks behind successful legal technology companies. Each episode dives into how Legal Tech companies actually win, covering sales strategy, market positioning, GTM hiring, and the lessons learned while scaling. Hosted by Paul Church, founder of Talent & Growth and specialist recruiter for Legal Tech go-to-market talent. New episodes every week.

  1. 16. Okt.

    The AI Law Firm Coming After Kirkland & Cleary | Daniel Dalla Vedova | Founding COO: Moritz

    Daniel Dalla Vedova is the co-founder of Moritz, an AI-native law firm that came out of Y Combinator and now operates across 44 countries. Before building Moritz, Daniel sold legal AI to some of the biggest law firms in the world. Then he cancelled every single contract. In this episode, Daniel explains why routing AI-native legal services through traditional law firm billing was always going to be the wrong model, how Moritz competes directly with Kirkland and Cleary (and hasn’t lost a single bake-off), and why complexity is the only defensible moat left in legal tech. Clients include Eleven Labs, Turing, and Pylon. 100% bake-off win rate. Operating in 44 countries. 00:00 Introduction - What is Moritz?01:00 The BigLaw pivot - why Daniel cancelled every law firm contract02:58 Client feedback and end-of-quarter intensity03:27 Ideal client profile - who Moritz serves05:01 Career background - BigLaw, Norm AI, and the ChatGPT moment08:48 How much more will AI eat up? When does it get uncomfortable?10:00 Selling to law firms vs. going direct to in-house teams11:13 Go-to-market - how clients find Moritz12:34 The bake-off win rate - three reasons Moritz hasn’t lost one15:22 What’s been harder than expected17:56 Recruiting parallels and the product that changes its mind18:30 If you had to double down on one GTM motion20:17 Hiring salespeople - unreasonable targets and fast feedback cycles22:21 What percentage of sales hires don’t make the cut?23:03 How performance is measured beyond sales roles25:10 Where is Moritz going in the next 12 months? Coming after Kirkland and Cleary27:01 What the business needs to do to get there30:11 Is LegalTech in a bubble?34:17 Wrap-up 🎙️ Taking LegalTech To Market is hosted by Paul Church, LegalTech recruiter and founder of Talent & Growth.

    The AI Law Firm Coming After Kirkland & Cleary | Daniel Dalla Vedova | Founding COO: Moritz
  2. 9. Okt.

    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 actively using the product. The growth engine is a combination of network, conference speaking, and proof-of-concept pipelines that run through tech review, litigation partners, and business committees before a single dollar changes hands. In this episode Dan covers the full picture: why mock trials happen too late and what that costs trial teams, how Courtroom was built around not training on client data and why that single decision has won deals, the shift from technology demos to customer-outcome selling, and what 41 years in war rooms at 3am taught him about building software for burnt-out lawyers. He also talks about the judge application now in co-development, the Thoughts from the Trenches LinkedIn series he just launched, and why the AI replacing parts of his craft feels like a natural evolution rather than a threat. If you're building in litigation tech or selling AI into law firms, this is the most grounded version of what that actually looks like. Timestamps [0:00] — From the trenches to co-founder: Dan's 41-year journey[2:20] — How Courtroom came together by accident[4:00] — Market reception: huge interest, cautious buyers[5:00] — Breaking into Am Law 100: the proof-of-concept pipeline[8:10] — Who kills the deal: tech, partners, or the business committee?[11:40] — "We don't train on client data", how that wins deals[12:55] — Go-to-market: networks, conferences, and Thoughts from the Trenches[15:00] — Keeping the focus on the customer, not the technology[17:00] — Selling to burnt-out lawyers at 3am[19:50] — Watching AI remove what you've spent 40 years building[23:30] — The next 12 months: what world-class looks like for Courtroom 🎙️ Taking LegalTech to Market is hosted by Paul Church, LegalTech recruiter, talent advisor, and one of the most listened-to voices in the space. Subscribe to our Newsletter: https://www.linkedin.com/newsletters/the-gtm-brief-7499116024424873984/

    How To Sell When Every Buyer Has Seen 50 AI Tools Already | Dan Gallipeau | Courtroom
  3. 2. Okt.

    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 own network and existing clients referring founders they went through incubators with. In this episode Luke covers the full picture: why they chose a tech-enabled professional services firm over a SaaS product, how the squad model works and why it creates a moat that an arm's length law firm can't replicate, what the Atrium lesson taught them about building economics that work from day one without needing AI to save them, and the unreasonable hospitality playbook they're about to run to turn clients into advocates. He also talks about the community play, a free cap table rolling out to all clients, hiring a head of hospitality, and why headcount is the wrong metric entirely. If you're building a startup and thinking about legal and back office, or building a professional services business and wondering what the new model looks like, this is the most practical version of that story. Timestamps:00:00 — What Virgil is and who it serves01:01 — How Luke met Eric Rees and what Incorruptible had to do with it04:38 — Why they chose professional services over SaaS06:36 — 100 clients, zero marketing, entirely word of mouth10:56 — Why the wait list worked when Luke assumed it wouldn't13:14 — The ICP moment when the need slaps founders in the face16:21 — Unreasonable hospitality as a GTM strategy20:00 — Making promos for clients for free as a referral flywheel22:45 — Surprising clients by including things they expected to pay for23:49 — The community play: Bookface for Virgil clients25:56 — Why they didn't raise and what Atrium taught them30:12 — Headcount is a vanity metric. We brag about how few people it takes. 🎙️ Taking LegalTech to Market is hosted by Paul Church, LegalTech recruiter, talent advisor, and one of the most listened-to voices in the space. Subscribe for new episodes every week. Subscribe to our Newsletter: https://www.linkedin.com/pulse/why-first-ae-hire-fails-companies-paul-church-jrpme/

    100 Clients and Zero Marketing Spend | Luke Versweyveld | Co-Founder & CEO: Virgil
  4. 25. Sept.

    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 episode Matt covers the full picture: why selling to law firms was the wrong model and what made that clear, how a $40K fee to close a $2M mortgage loan forced him to throw out the model and run it like an ALSP, what happens when you promise a fixed fee and then lose money on a deal, why a 20-person team of well-equipped lawyers should be able to do the revenue of a 150-person firm, and why the AI native law firm conference in New York is exciting precisely because nothing is right or wrong yet. Matt also talks about building MCP integrations with Claude, why AI agents sound better than they perform in complex deal space, why you still need a really good human in the loop, and what it feels like to ship something in a week that would have been technically impossible a year ago. If you're building or selling in commercial real estate legal, interested in AI native law firms, or trying to understand what the transition from law firm to legal tech company actually looks like from the inside, this is the most honest version of that story. Timestamps:00:01 — What Naya does and who it's for01:22 — Building Naya while billing 2,000 hours a year as a senior associate02:04 — The tension between selling efficiency and billing hours04:51 — Why selling into large law firms is harder than it looks07:10 — Law firms as archipelagos: you've signed the firm, you've reached one partner09:01 — The pivot: from law firm software to ALSP for mortgage lenders11:23 -- $40K to close a $2M loan: why the big firm model didn't work13:43 — Fixed fee deals, early losses, and what they taught him to automate16:40 — AI first, tech first, but lawyers aren't going away in complex deal space22:12 — LinkedIn content: why Matt started posting and what's working25:50 — The channel mismatch: LegalTech audience vs mortgage lender buyers28:25 — Why lawyers are scared to post and why that's an opportunity33:48 — Can a 20-person team do the revenue of a 150-person firm?35:01 — North Star: competing head to head with AM Law 150 for CRE finance deals36:48 — Building MCP with Claude and what became possible last week that wasn't possible a year ago 🎙️ Taking LegalTech to Market is hosted by Paul Church, LegalTech recruiter, talent advisor, and one of the most listened-to voices in the space. Subscribe for new episodes every week. Subscribe to our Newsletter: https://www.linkedin.com/newsletters/the-gtm-brief-7499116024424873984/

    We Were Selling Efficiency. They Were Selling Hours. Something Had To Break | Matthew Basile | CEO: Naya Law

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Taking Legal Tech To Market is the podcast where Legal Tech founders and revenue leaders break down the real go-to-market playbooks behind successful legal technology companies. Each episode dives into how Legal Tech companies actually win, covering sales strategy, market positioning, GTM hiring, and the lessons learned while scaling. Hosted by Paul Church, founder of Talent & Growth and specialist recruiter for Legal Tech go-to-market talent. New episodes every week.

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