AI won't shrink legal. It'll make it bigger.
Updated: 4 days ago
Andrew Hutchinson, Founder of Rebel.Group, in conversation with Tim Kenney at ILTACON 2026
Walk the ILTACON 2026 exhibit hall and you'd think AI is about to hollow out the legal profession. Andrew Hutchinson thinks the opposite. Back on People in Legal by popular demand, "Hutch" told Tim Kenney that the AI boom is running on investor money rather than client need, that the legal tech acquisition model is broken, and that AI is more likely to create billable work than destroy it.
Two decades in legal tech
Hutch has spent 23 years in legal tech, and by his own account nobody gets into it on purpose. He joined his first company in his early twenties, lured by the annual company trip to Spain. It was acquired by LexisNexis.
From there he moved to Toronto to resell iManage, then joined OnePlace, the first legal CRM built on Salesforce, as employee number five. OnePlace was acquired by Intapp in 2019, and Hutch spent two years there helping shape what DealCloud could look like for law firms. He then left big legal tech to found his own intelligence business, later merging it into another company. (PIL co-founder David Woolstencroft had a hand in two of those career moves, reportedly over a couple of bottles of red.)
That experience shaped Rebel.Group.
Why acquisitions fail clients
Hutch says that when legal tech companies get acquired, the same two things tend to happen. He sees it as an industry-wide pattern.
First, the founders, the people with the passion and the subject-matter expertise, are incentivised to leave. Clients who invested in the product are, in his words, "left holding the baby," and a steady decline follows. He reckons he and Tim could name at least 20 examples.
Second, the products themselves stop being great. Hutch says nobody really likes using some of the institutional vendors that have been around for three decades; firms just end up using them. Inside big legal tech, he adds, founders lose their independence and end up queuing for development resources instead of building.
Rebel.Group's answer is a hybrid of a private equity model and a partnership. Like-minded founders bring their products into a shared portfolio that the founders themselves own. Sales, marketing and finance are centralised so each founder can focus on product. The stated goal is a business too big to be acquired, while still giving founders a path to take money off the table without hurting clients.
"We will be successful not because of the technology that we bring together, but because of the people that we bring together."
Four or five months in, he says it's going well. His first test was whether other founders would come into the portfolio, and they have. The next is whether clients will buy several products from it.
The bicycle, not the rocket
Hutch's critique of the AI rush comes from a client he once worked with at a big vendor:
"I just want a bicycle to cycle to the corner shop, buy some groceries, and come home. You keep trying to sell me a rocket to get to Mars."
His view is that vendors are trying to accelerate law firms "in a very unnatural way" and that most firms aren't ready. The fix is to solve the basics first. In Rebel.Group's world, that means something as unglamorous as helping an events team print name badges, a job that takes far longer than it should. Take that off their plate, and you free up time to give them real intelligence: which events work, which don't, and who is actually engaging.
Investment, not need
When Tim asked how anyone justifies a 53x multiple on a legal AI product, Hutch didn't hedge: "It's not defensible."
Then he went further. Legal, he argues, has made more money every decade for over a century, because the world keeps getting more litigious and more regulated. Anyone expecting AI to shrink that is mistaken.
He offered a real example. A firm uses AI to draft a document, a partner vets it, and it goes to the client. The client runs it through their own AI and comes back with 20 questions they would never have asked before. The firm saved time on drafting and now bills to answer the questions. The outcome is arguably better for everyone, but it is not less legal work.
His one-line reminder to anyone predicting the end of lawyers: the legislators and the judges started as lawyers too.
Where AI genuinely helps: data and pricing
Asked for a 12-month prediction, Hutch hedged. He would like to think firms will have woken up to what AI is actually doing for them, but with so much money fuelling the hype — exhibitor stands at ILTACON are now "bigger than any house I've ever owned" — he isn't counting on it. The biggest gap today is measurement. Most firms can't tell whether AI was used on a task, and few track phases and tasks in time recording because partners resist it.
That's where he sees the real opportunity. Automated time capture can produce the granular data firms have never had, and that data unlocks:
Credible alternative fee arrangements, priced on what similar work actually took.
Pipeline forecasting, projecting forward from known phase and task effort.
Smarter staffing, matching partners and associates to the stages they're best at, against each client's time and budget constraints.
Might that save clients money? Possibly. Might it justify charging more? Also possibly. His example: if winning a matter adds $50 million to a client's revenue, a $1 million fee is one they'll pay "all day long."
What law firm leaders should take from this
Fix the basics before buying the moonshot. The quickest wins are often admin tasks nobody wants to own.
Put vendor ownership into due diligence. Ask who the founders are, whether they'll stay, and what happens to the roadmap if the company is sold.
Measure AI use before you claim AI savings. Without task-level data, you're guessing.
Use AI-generated data to price, not just to produce. The biggest return may come from better fee arrangements and staffing, not faster drafting.
Tim's closing bet: they'll check back in a year, and if Hutch is wrong, he buys the drinks.
Watch the full conversation
This episode is part of People in Legal's ILTACON 2026 coverage, alongside conversations with leaders from ILTA, iManage, NetDocuments, BigHand, Cicero and more.
Quotes lightly edited for clarity.
People in Legal is where legal leaders and legal technology meet. Want your leaders in front of our audience at the next event? Partner with us or email team@peopleinlegal.com.
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