Episode overview

Elena Tsalanidis flew from Melbourne to Sydney at Steve Grace’s request after he saw Deeligence’s raise and wanted to understand a legaltech company that was genuinely different from what had come before. The episode covers what due diligence actually is, why lawyers hate it, how AI is now capable of doing the extraction and summarisation work that once ate junior lawyer hours, and why a career that bounced through Buckingham Palace, the Supreme Court, and the Commonwealth Secretariat was precisely the preparation for founding a high-trust AI product in a risk-averse industry.

What due diligence is and why lawyers dread it

When a business is bought or sold, lawyers are hired to check it for risks. They work through a data room, a repository of hundreds or thousands of documents, finding the needles in the haystack and compiling them into a client report. The word that came up again and again in Deeligence’s customer interviews was “nightmare.” Not difficult. Not time-consuming. Nightmare. The work is skilled enough to require a qualified lawyer but repetitive enough to drain the most motivated person in any firm. Junior lawyers describe it as spending three years doing the worst part of the job before they can get near anything interesting.

Why security had to come before everything

Elena is clear that the enterprise-grade security build was not optional. Law firm customers think about their systems like banks think about theirs. The confidential information in an M&A data room is among the most sensitive in any transaction. Building military-grade security was table stakes before the first sales conversation. It was also significantly more expensive than a standard SaaS build, but Elena describes it as unavoidable. Once security is established as a given, the conversation can shift to the actual value proposition: doing the document extraction and summarisation work faster and with less risk.

A career designed for this, without knowing it

The career path Elena describes reads like someone building an unusual founder profile by accident. Working at Buckingham Palace before law school because she wanted to do something legal-adjacent in London. Spending time as a judge’s associate and noticing she could help him process his judgment workload dramatically faster through systematic organisation. The Commonwealth Secretariat. A move into legaltech at Lexoo, where she first saw tech applied to legal process improvement at scale. She describes each step as contributing to a toolkit she did not realise she was building until she needed it all at once.

Where AI works in legal and where it does not

Elena is careful to position Deeligence within what AI can actually do reliably rather than what the hype might suggest. Extraction and summarisation from structured document types is where AI performs above 90% accuracy consistently. Deeligence is not building AI that replaces legal reasoning or judgment. The platform is designed to take the parts of due diligence that are repetitive and document-intensive and automate those, so lawyers can spend their time on the judgment calls that actually require a qualified mind. This is the pitch that converts sceptical senior partners.