𝗪𝗵𝗮𝘁 𝗶𝗳 𝘆𝗼𝘂 𝗰𝗼𝘂𝗹𝗱 𝗳𝗼𝗿𝗺𝗮𝘁 𝗮 𝗹𝗲𝗴𝗮𝗹 𝗱𝗼𝗰𝘂𝗺𝗲𝗻𝘁 𝗷𝘂𝘀𝘁 𝗯𝘆 𝗮𝘀𝗸𝗶𝗻𝗴?

At #ILTACON2026, David Woolstencroft sat down with Chris Cangero, co-founder of DocStyle, who has spent 25 years in legal tech. He grew up with Wang terminals in the family garage, and he and co-founder Adrian Bailey have now bootstrapped the business for almost 17 years.

Their latest launch is DocStyle AI. It connects their mature document tools to the LLM of your choice through an MCP server. The interesting part is how they got there. Their first attempt was to build AI into the product. Three months in, they scrapped it and started over. Now the LLM handles the conversation, and DocStyle's deterministic tools do the precise work.

The result: you can say "style this in our house template and add a table of contents using level one headings only" and it gets done. You don't need to know which button to press. In their internal benchmarks, it's 99.3% more token efficient than using an LLM on its own, and a full paper is coming soon.

Chris's message to firms was clear: don't replace your word processing teams. Free them up for the documents only they can fix, and let lawyers handle the other 80% themselves, even at midnight.

#LegalTech #ILTACON #PeopleInLegal #LegalAI #DocumentAutomation

"There had to be a better way than PowerPoint."

At #ILTACON2026, Tim Kenney sat down with Tim Follett and Neal Chatrath of StructureFlow, and that line is where it all started.

Tim was a corporate lawyer doing private equity fund structuring, building structure charts by hand. So he built a data-driven, AI-enabled platform that turns complex relational information (entities, documents, assets, people) into structure charts, flow charts and timelines automatically.

Neal brings something unusual to a legal tech conference: a career in fintech, across hedge funds and the service providers behind PE funds and investment banks. He's now StructureFlow's first senior hire in North America, based in New York, where most of their revenue already comes from. His job: go deeper with law firms, and build the bridge to their clients. One month in, those clients are already asking their lawyers, "How are you doing this?"

The biggest takeaway? The AI conversation is shifting. It's less about the models and more about the context we give them. "Ontology" was the word of the week, and structured, mapped data is something both a human and a machine can navigate.

Next up for StructureFlow: a graph-based data layer you can point at your document repositories and systems of record. Diagramming is where it started. It's not where it ends.

Thanks Tim and Neal for joining us on People in Legal, and congratulations on the North America expansion.

Is AI finally going to kill the billable hour?

People have been predicting its death for decades. Maurice Tunney thinks this time might actually be different.

David Woolstencroft had a great conversation with Maurice, Director of Technology and Innovation at Keystone Law, about AI, technology and the very different platform model behind Keystone.

Maurice has worked in legal for 25 years and has heard the “death of the billable hour” conversation throughout his career. But with AI now dramatically reducing the time needed for certain types of legal work, his view is that something fundamental has to change. If the time required to do the work is being slashed, can firms really keep charging for time in the same way?

They also talk about Keystone’s unique operating model, building technology around how lawyers actually work, practical AI adoption, and one lawyer who has grown his practice by around 60–70% with AI helping, under close supervision, with drafting, analysis and chronology work.

A fascinating conversation about what AI might really change inside a law firm, beyond simply adding another tool to the tech stack.

Chapters
0:00 Intro
0:31 Meet Maurice
3:46 The 15% Referral Incentive
5:06 The Happiest Law Firm
6:22 Why Lawyers Join
8:14 Building From Scratch In The Cloud
13:00 Choosing The Tech Stack
17:40 The AI Pressure
19:43 Keybot And Secure ChatGPT
23:00 When Clients Use ChatGPT
24:44 The Death Of The Billable Hour
27:42 AI As The Junior
28:45 Picking The Big AI Tools
30:31 Rolling Out AI Without Overload
32:29 A Year From Now

Guest: Maurice Tunney, Director of Technology and Innovation, Keystone Law
Host: David Woolstencroft

People in Legal — where legal leaders and legal technology meet.
https://www.peopleinlegal.com/
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𝗪𝗵𝗮𝘁 𝗵𝗮𝗽𝗽𝗲𝗻𝘀 𝘄𝗵𝗲𝗻 𝘆𝗼𝘂𝗿 𝗔𝗜 𝗯𝗶𝗹𝗹 𝗷𝘂𝗺𝗽𝘀 𝗳𝗿𝗼𝗺 $𝟭𝟱,𝟬𝟬𝟬 𝘁𝗼 $𝟲𝟬,𝟬𝟬𝟬 𝗮 𝗺𝗼𝗻𝘁𝗵?

At #ILTACON2026, Tim Kenney sat down with Peter Geovanes, Founder of Juris Tech Advisors, LLC, to talk about where law firms are really up to with AI.

Peter works with firms at very different stages, from choosing tools and identifying use cases to training lawyers, managing governance and working out what AI means for pricing and client conversations.

One issue getting much harder to ignore is AI consumption costs. Peter shared an example of a firm moving from roughly $15,000 a month to more than $60,000, with some lawyers generating around $1,000 a day in token costs.

That raises a bigger question: if AI saves hours of lawyer time but creates a significant technology cost, how should firms price that value for clients?

They also get into knowledge management, shadow AI, better prompting, and why Peter believes a well-structured prompt can sometimes deliver better results without always reaching for the most expensive model.

“𝗜 𝗷𝘂𝘀𝘁 𝘄𝗮𝗻𝘁 𝗮 𝗯𝗶𝗰𝘆𝗰𝗹𝗲 𝘁𝗼 𝘁𝗵𝗲 𝗰𝗼𝗿𝗻𝗲𝗿 𝘀𝗵𝗼𝗽. 𝗬𝗼𝘂 𝗸𝗲𝗲𝗽 𝘁𝗿𝘆𝗶𝗻𝗴 𝘁𝗼 𝘀𝗲𝗹𝗹 𝗺𝗲 𝗮 𝗿𝗼𝗰𝗸𝗲𝘁 𝘁𝗼 𝗠𝗮𝗿𝘀.”

At #ILTACON2026, Tim Kenney sat down with Andrew Hutchinson, Founder of Rebel.Group, to talk acquisitions, AI hype and what law firms actually need.

After more than 20 years in legal tech, Hutch has seen the same pattern play out again and again: companies get acquired, founders move on, and the people with the passion and deep product knowledge disappear with them.

𝗥𝗲𝗯𝗲𝗹.𝗚𝗿𝗼𝘂𝗽 𝗶𝘀 𝘁𝗿𝘆𝗶𝗻𝗴 𝘀𝗼𝗺𝗲𝘁𝗵𝗶𝗻𝗴 𝗱𝗶𝗳𝗳𝗲𝗿𝗲𝗻𝘁.

And on AI? Hutch isn’t buying all the hype.

His view is simple: 𝗳𝗶𝘅 𝘁𝗵𝗲 𝗯𝗮𝘀𝗶𝗰𝘀 𝗳𝗶𝗿𝘀𝘁. Remove the painful manual work. Give people their time back. Then start layering intelligence on top.

They also get into whether AI will really reduce legal spend, whether today’s valuations make sense, and why better data could completely change pricing and how firms resource matters.

#PeopleInLegal #ILTACON2026 #WeAreILTA #LegalTech #LegalAI

𝗦𝘁𝗶𝗹𝗹 𝗺𝗮𝗻𝗮𝗴𝗶𝗻𝗴 𝗮 𝗹𝗶𝘁𝗶𝗴𝗮𝘁𝗶𝗼𝗻 𝗽𝗼𝗿𝘁𝗳𝗼𝗹𝗶𝗼 𝗶𝗻 𝗮 𝘀𝗽𝗿𝗲𝗮𝗱𝘀𝗵𝗲𝗲𝘁?

At #ILTACON2026, Tim Kenney sat down with Robert Martorana from Theo Ai and Pamela Fehring (JD, CIPP/US), an 𝗔𝗜 𝗘𝗻𝗮𝗯𝗹𝗲𝗺𝗲𝗻𝘁, 𝗚𝗼𝘃𝗲𝗿𝗻𝗮𝗻𝗰𝗲 & 𝗘𝘁𝗵𝗶𝗰𝘀 𝗟𝗲𝗮𝗱𝗲𝗿, to talk about litigation defence intelligence and why the corporate legal side has been somewhat overlooked in the AI rush.

When Theo AI spoke with in-house legal teams, one answer kept coming back: many were still managing litigation portfolios through spreadsheets, pulling information manually from billing systems, document management systems and other sources.

Theo AI takes a different approach, bringing that information together so legal teams can see not just one matter, but their 𝗲𝗻𝘁𝗶𝗿𝗲 𝗹𝗶𝘁𝗶𝗴𝗮𝘁𝗶𝗼𝗻 𝗽𝗼𝗿𝘁𝗳𝗼𝗹𝗶𝗼 in one place. That opens the door to better benchmarking, outside counsel spend decisions, settlement strategy and identifying trends before they become bigger problems.

Robert also shared why Theo AI chose to focus specifically on the 𝗱𝗲𝗳𝗲𝗻𝗰𝗲 𝘀𝗶𝗱𝗲 𝗼𝗳 𝗹𝗶𝘁𝗶𝗴𝗮𝘁𝗶𝗼𝗻, where they saw far fewer AI solutions compared with the plaintiff side.

The bigger idea? Helping legal departments move from 𝗿𝗲𝗮𝗰𝘁𝗶𝘃𝗲 𝘁𝗼 𝗽𝗿𝗼𝗮𝗰𝘁𝗶𝘃𝗲 by actually using the data they already have.

𝗛𝗼𝘄 𝗺𝗮𝗻𝘆 𝗔𝗜 𝘁𝗼𝗼𝗹𝘀 𝗱𝗼 𝘆𝗼𝘂 𝗮𝗰𝘁𝘂𝗮𝗹𝗹𝘆 𝗻𝗲𝗲𝗱 𝗱𝗼𝗶𝗻𝗴 𝘁𝗵𝗲 𝘀𝗮𝗺𝗲 𝘁𝗵𝗶𝗻𝗴?

At #ILTACON2026, David sat down with Heath Harris, MBA, VP, Applied AI, Enterprise Transformation at NetDocuments, to talk about what AI transformation actually looks like inside a law firm.

Heath works with firms around the world on designing and implementing AI strategies, then brings those lessons back into product development at NetDocuments.

One thing that stood out was his approach to AI investment. Rather than starting with the product, start with the activity.

- What do you need for workflow?

- Search?

- A chat assistant?

- And how do you deploy those capabilities responsibly without buying five tools that solve the same problem?

They also talked about NetDocuments’ work with Google Gemini and Legora, the role of MCP, and the growing challenge for firms around governance, security and avoiding a “shadow DMS” as more AI tools enter the business.

And perhaps the most useful message for firms feeling behind:

𝗞𝗲𝗲𝗽 𝗹𝗲𝗮𝗿𝗻𝗶𝗻𝗴. 𝗞𝗲𝗲𝗽 𝗺𝗼𝘃𝗶𝗻𝗴.

You don’t need to have everything figured out today. Progress matters more than chasing every new thing that appears.

💡 A great conversation about cutting through the AI noise and focusing on what is actually practical.

#PeopleInLegal #ILTACON2026 #WeAreILTA #LegalTech #LegalAI