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 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. 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. 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? 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. Timestamps: 00:00 — What top law firms are saying about AI right now 00:44 — Build vs buy: Kirkland Ellis, Freshfields, Harvey, Legora 03:22 — How Definely's GTM motion changed as AI took over drafting 05:30 — Why you can't use AI to verify its own output 07:23 — The independent verification layer law firms actually need 08:15 — What the first conversation with a top 50 firm partner sounds like 10:21 — Pilot process: why vendors kill their own deals 13:30 — Honesty upfront: naming what you can't do before the pilot starts 13:30 — Treating pilots as a project: Gantt charts and mutual action plans 15:49 — One license. Then 90-95% conversion. What changed. 16:13 — Building a repeatable pilot process from a failed first attempt 18:36 — US expansion: 1% to 30% revenue without a US office 18:36 -- Iltacon and conference-led relationship building 21:00 — Stakeholder mapping beyond the obvious C-suite 25:00 — Nine AI tools connected via MCP: what that looks like in practice 27:00 — Data hygiene: why you can't put client data in free ChatGPT 29:30 — Account coverage going from 40% to 80% with AI assistance 31:20 — CRM updates: from 1 hour to 10 minutes with automated MEDDIC mapping 33:20 — Meeting prep automated via Claude and Google Calendar 35:42 — Where AI should and shouldn't sit in a LegalTech sales motion 37:30 — The value calculator built using Thomson Reuters and Pursuit data 39:56 — Final advice: find your moat before Harvey and Legora find it for you 39:56 — When to hire a VP of Sales vs staying in founder-led sales 44:40 — Closing thoughts 🎙️ Taking Legal Tech 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. Follow Links: Nathan Killick   / nk-legaltech   https://www.definely.com Follow Links: Paul Church   / paulrichardchurch   http://www.talentandgrowth.io