Episode Summary:
Would you trust AI to help close a multi-million dollar acquisition? That’s exactly what Deeligence is helping lawyers do faster and with fewer headaches.
In this episode of Pick My Brain, Elena Tsalanidis, co-founder of Deeligence joins Alan Jones to pitch her AI-powered legal tech startup. Elena shares how her platform streamlines the M&A due diligence process for lawyers, cutting review time in half while delivering greater accuracy.
Alan and Elena dive deep into B2B SaaS sales strategy, how to stand out in a sea of AI wrappers, and what actually makes a startup defensible when everyone’s using the same language models. They explore how founders can navigate complex enterprise sales cycles, why law firms resist change, and how product distribution (not tech) is the real moat.
If you’re building in legal tech, enterprise AI, or B2B SaaS, you’ll want to take notes.
Episode Sponsors:
Chapters:
01:40 – What is Deeligence? AI-powered legal due diligence for M&A lawyers
03:05 – Elena’s background: ex-lawyer, ex-legal tech startup operator
04:15 – Childhood ambitions: politics, drill sergeant energy, and leadership
06:00 – The challenge: how do AI startups prove real product differentiation?
08:30 – Alan on “thin wrappers” vs customer experience as a moat
10:10 – Building trust in professional services: security, UX, and reliability
11:40 – Why distribution beats tech in B2B AI
14:10 – What makes a moat in the era of fast, AI-powered software
16:05 – How deal size affects sales cycles in enterprise SaaS
17:15 – Selling into law firms: why Hobart offices can be a strategic wedge
20:00 – Innovation teams: gatekeepers, champions… or blockers?
22:00 – The danger of general-purpose tools vs specialist point solutions
25:05 – How to respond when clients say “we’ll build it in-house”
27:00 – Why law firms are fast-moving money machines (and hate friction)
Resources:
👩⚖️ Elena Tsalanidis – https://www.linkedin.com/in/elenatsalanidis
⚖️ Deeligence – https://www.deeligence.ai
🎧 More from Alan Jones – https://www.startupfoundercoach.com
