Tom Dunlop and the problem with one more question

The first 500 contracts were bad enough. Tom Dunlop had worked through them during an acquisition, extracting the information the business needed. Then the chief financial officer wanted to know about another clause. Answering meant going back through the documents. A lawyer’s completed assignment had become a repeat assignment, with almost admirable efficiency.

This is an unglamorous place to begin a technology company. There is no dramatic invention, just a knowledgeable person doing work that ought to be easier. Dunlop’s irritation became the starting point for Summize, the business he co-founded with software developer David Smith in 2018. Its first proposition was narrow: turn a contract into a useful summary.

By January 2026, Summize was announcing $50 million in investment. It had travelled from a document problem to a business with offices on both sides of the Atlantic. The distance between those two facts contains the more interesting story: a sporting ambition set aside, an early business experiment, professional friendships, and a founder who had to learn that encouraging customers can still send you in the wrong direction.

Before the contracts, the court

Dunlop grew up expecting badminton to take him to the Olympics. Sport occupied the centre of his plans; law was something he studied alongside it. His younger years involved fitting training around education and competing internationally. Eventually, the two careers demanded a decision. He chose law.

The discipline survived the choice. His public conversations about business repeatedly return to the accumulation of small gains. An athlete has ample opportunity to discover that improvement can be irritatingly gradual. A practice session rarely provides a satisfying conclusion. You return, change something, and see whether it helps.

In 2021, Dunlop described a Summize meeting held at five on a Friday, dedicated to making the following week a little better. The team examined its processes, tried changes and measured the results. Useful changes stayed; unsuccessful ones went. The meeting had a suitably modest name: 1% better.

There is a comic audacity to putting process improvement in the diary at the precise moment a working week might reasonably consider itself finished. Yet the routine explains something about his preferences. He likes an improvement that can be attempted, observed and repeated. A small gain gives ambition a job to do.

A business before the business

Summize was not Dunlop’s first attempt to make legal services easier to navigate. While at law school, he started comparelegalsolutions, a website comparing solicitors on price, distance and quality. Firms signed up, the project attracted attention, and the development costs were covered. It ran for several years.

His first legal job offered an unusual overlap of interests. Prosperity Law also operated in sports management. Dunlop could apply his legal training around athletes, sponsorships and commercial negotiations while keeping a connection to the world he knew. A legal career did not require him to leave every earlier interest at reception.

What increasingly appealed was proximity to business decisions. Giving advice interested him; helping management decide what to do interested him too. Moving in-house offered more of that daily involvement. His subsequent technology-company career included AppSense, Zuto and UserZoom.

At AppSense, the professional connections became consequential. He met Smith, his future co-founder. Entrepreneur Charles Sharland, associated with AppSense, would become an early Summize backer. The later company grew partly from relationships formed while its founders were occupied with another company’s problems. Networks can sound abstract until the person you need is someone whose judgement you already trust.

An engineer, a coffee shop, a choice

The contract problem brought Dunlop’s legal experience into contact with Smith’s technical experience. The pair held early working sessions at the Starbucks in Birchwood. It is an appropriately practical address for a company concerned with making everyday work less awkward: somewhere to sit, talk, and test whether an idea makes sense.

Dunlop had been collecting business ideas in a little black book. He has cheerfully acknowledged that many were irrelevant. The contract idea persisted because it came from work he understood, with frustrations that other in-house lawyers recognised. A prototype gave the conversation something more substantial than conviction.

His recollection of those early sessions is strikingly restrained. Building a large company was not the immediate purpose. The question was whether technology could solve this particular problem. Confidence followed the prototypes and the responses to them.

That sequence matters to his story. Dunlop had already moved from sport to law, then towards technology businesses. Starting Summize asked him to make another choice about where to put his time. Eventually, a product with customers and investment required his full attention. The side project had acquired obligations of its own.

“Listening to customers and staying close to the market is core to how I operate.”

Tom Dunlop

The trouble with encouraging noises

Knowing a problem intimately did not immediately tell Dunlop which market to pursue. For about 18 months, Summize sought business across law firms, in-house legal teams and companies of varying sizes. Prospects were encouraging. Some bought. Enough possibilities remained alive to make choosing difficult.

The conflicting demands reached the product roadmap. A law firm might want a client portal. An in-house team might want a Salesforce integration. Both requests could be reasonable, while taking a small software company towards quite different destinations. Listening to everyone had consequences.

The company eventually concentrated on in-house legal teams at mid-market businesses. That brought it closer to Dunlop’s own experience and gave its sales effort a more specific audience. He could describe a working day he had actually lived.

The episode complicates the tidy founder narrative in a useful way. A real frustration produced a plausible product. Neither automatically supplied a repeatable business. Dunlop still had to distinguish interest from demand, then accept that focus meant disappointing some possible customers. An agreeable meeting is pleasant compensation for an afternoon. It is less dependable as a strategy.

Leave the lawyer in Word

Dunlop’s product argument starts with the applications people already use. Lawyers work in Word. Colleagues make requests through email, Teams or Slack. Summize embeds contract workflows in those familiar settings, letting the legal team’s rules reach people outside the legal department.

The idea also reflects how the original product changed. A summary answers an immediate question about a signed agreement. Customers then want to know what happens next. Summize expanded into the steps around requesting, drafting, negotiating, signing and storing contracts. The summary became part of a longer working relationship.

In conversations about implementation, Dunlop spends time on a less photogenic subject than artificial intelligence: getting colleagues to use the thing. He encourages teams to examine their existing processes, identify the people involved and bring them into the buying discussion early. Sales, procurement and finance have their own requirements. Legal cannot wish those away.

There is a recognisable continuity with his earlier career. He wanted to work alongside management, and his software now has to work alongside the rest of a business. Its usefulness depends on crossing that boundary. The legal department gets little benefit from a beautifully organised system its colleagues continually walk around.

When the props refuse to cooperate

Dunlop’s account of a presentation provides a welcome interruption to the operational seriousness. Trying to make a talk entertaining, he brought props. Three of the four went wrong. Anyone who has watched a demonstration acquire independent artistic ambitions will recognise the situation.

His response was practical: know the subject, know the audience, and know the three things people should remember. The unscripted moment might even be what stays with them. A founder can rehearse a presentation; an audience will still remember the rebellious prop.

He discussed that episode alongside Summize’s chief marketing officer, Laura Proctor. Their conversations about the product connect legal efficiency with how a legal team is perceived inside its company. Removing repeated requests can change the working relationship between departments, as well as the minutes spent on a document.

That ambition gives the business a more human measure than speed alone. Dunlop wants lawyers to have more room for judgement and advice. The work he enjoyed as an in-house lawyer remains present in the work he hopes to make possible for customers.

A larger team, the same desk

The scale of the assignment has changed. Summize’s January 2026 financing brought participation from Kennet Partners and Federated Hermes Private Equity alongside existing investors Maven Capital Partners and YFM Equity Partners. The funding supports expansion of the product, team and international customer base.

For the financial year ending June 30, 2026, the company reported 75% growth in annual recurring revenue, with 70% of its business coming from the United States. Manchester, Boston and San Diego now form the geographical setting for a founder’s recurring concern: keeping people pointed in the same direction.

In June, Summize acquired key personnel and proprietary assets from InnoLaw Group, adding experience in deploying contract technology. Lara Trope joined to lead implementation; InnoLaw founder Lucy Bassli remained independent. The distinction is telling. Helping a customer use software requires expertise as well as software.

Dunlop now describes setting direction and hiring as substantial parts of his role. He has acknowledged underestimating how clearly people need a sense of purpose. The founder who began with a task on his own desk must help colleagues understand the work ahead of them.

Sport has found a route back into the picture too. Summize serves professional sports organisations, and Dunlop has described the pleasure of watching teams whose contracts his business helps manage. The Olympic plan took another course. He still gets to follow the score, while attending rather more closely to the paperwork.