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.
Taking LegalTech To Market
Claim This Podcastby Paul Church
20 episodes
Updated Daily
Accepts GuestsHas Sponsors
Podcast Overview
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.
Language
🇺🇲
Publishing Since
4/8/2026
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Recent Episodes
June 12, 2026
His First Pilot Sold One License. His Pilots Now Convert at 95% | Nathan Killick | GTM Lead: Definely
<p><a href="https://www.linkedin.com/in/nk-legaltech/" target="_blank" rel="noopener noreferer">Nathan Killick's</a> first pilot at <a href="https://www.definely.com" target="_blank" rel="noopener noreferer">Definely</a> 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%.</p><p>That turnaround didn't come from the product. Definely is a great product. It came entirely from process, mutual action plans, Gantt charts, stakeholder mapping beyond the C-suite, and an obsessive checklist he runs on every single pilot without exception.</p><p>In this episode Nathan breaks down the full GTM picture: why law firms start pilots wanting to buy and how vendors kill their own deals; how he grew US revenue from 1% to 30% without a US office; why the SDR and AE functions at most LegalTech companies are structured wrong; how he automated 75% of his pilot process using Claude and MCP; and why the value calculator he built using Thomson Reuters data changed every business case conversation he has.</p><p>He also talks about what Freshfields going all-in with Anthropic signals for the broader market, why best-of-breed is starting to win against all-in-one, and the one question every early-stage LegalTech founder needs to answer before their next hire: if Harvey or Legora can absorb what you do, what's your moat?</p><p>If you're building or selling in LegalTech right now, this is the most commercially honest 45 minutes available on what GTM actually looks like in 2026.</p><p><strong>Timestamps:</strong>00:00 — What top law firms are saying about AI right now00:44 — Build vs buy: Kirkland Ellis, Freshfields, Harvey, Legora03:22 — How Definely's GTM motion changed as AI took over drafting05:30 — Why you can't use AI to verify its own output07:23 — The independent verification layer law firms actually need08:15 — What the first conversation with a top 50 firm partner sounds like10:21 — Pilot process: why vendors kill their own deals13:30 — Honesty upfront: naming what you can't do before the pilot starts13:30 — Treating pilots as a project: Gantt charts and mutual action plans15:49 — One license. Then 90-95% conversion. What changed.16:13 — Building a repeatable pilot process from a failed first attempt18:36 — US expansion: 1% to 30% revenue without a US office18:36 -- Iltacon and conference-led relationship building21:00 — Stakeholder mapping beyond the obvious C-suite25:00 — Nine AI tools connected via MCP: what that looks like in practice27:00 — Data hygiene: why you can't put client data in free ChatGPT29:30 — Account coverage going from 40% to 80% with AI assistance31:20 — CRM updates: from 1 hour to 10 minutes with automated MEDDIC mapping33:20 — Meeting prep automated via Claude and Google Calendar35:42 — Where AI should and shouldn't sit in a LegalTech sales motion37:30 — The value calculator built using Thomson Reuters and Pursuit data39:56 — Final advice: find your moat before Harvey and Legora find it for you39:56 — When to hire a VP of Sales vs staying in founder-led sales44:40 — Closing thoughts</p><p>🎙️ <strong>Taking LegalTech to Market</strong> is hosted by Paul Church, LegalTech recruiter, talent advisor, and one of the most listened-to voices in the space.</p><p>Subscribe for new episodes every week.</p>
June 11, 2026
Episode 10 (Trailer)
<p>One license. From a firm he already knew. After four months in the role.</p><p>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%.</p><p>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 needs to answer right now, if Harvey or Legora can absorb what you do, what's your moat?</p><p>Full episode live tomorrow. 🎙️ Taking LegalTech to Market.</p><p></p>
June 5, 2026
No Demo. No Sales Call. No Salesperson. Here's The GTM Model | Nick Holzherr | Founder: GitLaw
<p><a href="https://www.linkedin.com/in/nickholzherr/" target="_blank" rel="noopener noreferer">Nick Holzherr</a> 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.</p><p>80-90% of what you pay in a legal bill is overhead. AI makes that overhead free. But law firms are structured in a way that makes it almost impossible for them to pass those savings on. Which is why Nick didn't build <a href="http://www.git.law" target="_blank" rel="noopener noreferer">GitLaw</a> for law firms. He built it for the businesses that use them, and priced it at $20 a month with a free tier, no demos, no sales calls, and no salespeople.</p><p>In this episode Nick breaks down the full GTM model: why your real competitor in the SMB legal market isn't Harvey or Legora, it's ChatGPT and Claude; why activation is the only metric that matters when the product is self-serve; how referral-led growth works when every document you send is an invite opportunity; and why he thinks people hire sales teams far too early.</p><p>He also talks about the wrapper question every LegalTech founder is privately obsessing over, why a 15-person team can do the work of 100 with agents, what the LegalTech pricing stack looks like in 2027, and the one hiring framework that changes who gets interviewed for every commercial role.</p><p>If you're building, selling, or investing in LegalTech, this is one of the most commercially honest conversations about where the market is going.</p><p><strong>Timestamps:</strong>00:00 — Introduction00:50 — Why GitLaw sells to businesses, not law firms01:03 — Spending millions on legal fees: the personal problem01:03 — 80-90% of a legal bill is overhead. AI makes it free.03:39 — Positioning against ChatGPT and Claude, not Harvey or Legora03:57 — Why DIY legal AI gets you to court05:30 — Templates, human-reviewed forms and how GitLaw reduces hallucination06:54 — Will lawyers still be needed in five years?07:14 — The AI 2027 question and why Nick is genuinely scared08:21 — The law firm pyramid: juniors charged out at 5x their salary10:02 — Senior lawyers privately asking Nick about their pensions12:36 — What qualified pipeline looks like with no sales team12:58 — Activation is the bottleneck, not acquisition or conversion16:06 — Will GitLaw ever have a sales team?16:13 — Referral-led growth: how DocuSign, Dropbox and Calendly did it17:35 — How AI agents run GTM operations at GitLaw18:10 — The Slack agent that knows everything about the business22:38 — 15 people doing the work of 100 with agents23:33 — The wrapper question: good AI wrapper vs bad AI wrapper26:49 — Context, garden tending and taste as durable competitive advantages29:49 — GitLaw from 10 to 25 people: what triggers it32:07 — What LegalTech GTM looks like in 202734:56 — Best GTM decision of the last 12 months: hiring AI native people35:37 — Worst GTM decision: paid social didn't work36:02 — Contrarian view: you don't need a sales team as early as you think37:10 — Remote first: why AI works better with written context40:34 — Final advice: hire for the role in 18 months, not 3 years ago</p><p>🎙️ <strong>Taking Legal Tech to Market</strong> is hosted by Paul Church, LegalTech recruiter, talent advisor, and one of the most listened-to voices in the space.</p><p>Subscribe for new episodes every week.</p>
20 total episodes available
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