Legaltech Careers: Tom Dunlop, CEO & Founder of Summize

22 min readFeb 18, 2021


What do you get when you combine elite sports and a history of working in-house for various tech start-ups and scale-ups?

Tom Dunlop.

Tom is a former Team GB badminton player, in-house counsel, and now CEO and founder of Summize; a platform that creates instant contract summaries and assists users throughout the contract lifecycle.

It’s no surprise that Tom brings a fresh and unique perspective on legal, tech, business and life.

His guiding focus is Kaizen, the Japanese philosophy of continuous improvement — consistently improving something every day, little by little.

For Tom, if you want to achieve anything, it’s about going the extra mile and looking for small wins made every day that add up to big gains at the year end. It’s how Tom trained as a sportsperson, how he thinks about his own personal development and now how he runs Summize.

Where did your career begin? How did you find yourself in legaltech?

My start was unconventional. From my teens into my early twenties I was juggling professional level sports and studying. No easy task.

I was waking up early to train before school, and later university, while touring and competing around the world.

Towards the end of my law degree, I needed to choose between professional sports and law. Leading a double life meant increased demands. In the end, something had to give, and I chose to pursue a legal career.

What was your first career break?

My first foray into business was actually in law school. I founded an online comparison site, comparelegalsolutions.

It was the first solicitor comparison website on the internet, comparing solicitors by price, distance from the consumer, and quality.

It was reasonably successful, especially considering I was still juggling my degree and sporting career at this point.

Some of the early feedback I received when applying for training contracts was that I needed to develop my commercial awareness and experience. This was despite building a professional sports career, which included all of the commercial aspects that come with that.

So, rather than focusing on the usual things, I thought I’d try and start a business, which I was already — even at that stage of my career — thinking about for the long-term.

How did it pan out?

The site received a lot of buzz initially; we signed up a number of firms and garnered quite a bit of press coverage.

Together this paid off the development costs and we made a good run of it for a few years.

But then I landed my first legal job.

Again, it was a bit unusual. I joined a start-up law firm, Prosperity Law LLP, founded by an experienced lawyer who had been Legal Director for a variety of companies, including those in the British nuclear sector.

I was very lucky. Prosperity was set up as a law firm and sports agency at the time. It was a chance to combine my interests and experiences in sport with my legal background.

The other great thing was that it was very commercial and perhaps less typical for an entry level legal role.

What sorts of unconventional things did the role entail?

Aside from legal work, I got some great hands-on experience advising and assisting the management and strategy of Prosperity International Sports Management, which included finding new talent.

I worked on the contractual negotiations and sponsorship opportunities, and helped recruit Olympic athletes and footballers, including players at Premier League clubs and a number of ‘introducers’ to increase overall turnover.

That sounds like the perfect fit?

It definitely was at the time. It was an unusual route into becoming a trainee solicitor. But it was really fun learning the ropes within a business that was part law firm and part sports agency.

We also worked with a number of really interesting and large legal clients. Big clients like Metrolink, Manchester’s light rail system, and Palmer & Harvey.

I got to merge my legal, commercial and sports interests on the job, and had flexibility to keep up with my training and competitions around work.

It was important to me that I had a balanced career that didn’t shortchange my passion for sports.

Would you encourage law students to seek out these more diverse career opportunities?

Definitely. I’d encourage students to think outside the box when it comes to legal careers. Working in a huge law firm isn’t everything.

Sometimes smaller businesses can be a great way to quickly level up and take on exciting growth opportunities, which in larger organisations might have been deferred until much later.

With a bit of luck, a lot of grit and the right opportunities, you can find some surprising overlaps between your interests and your legal and commercial skills.

It’s not easy, but it’s worth it.

Did qualification as a lawyer change things or give you a new perspective?

Yes it did. In many ways it was a culmination of different thoughts I’d been having.

Having worked so closely with some impressive and interesting clients, I decided I wanted to do more of that, and felt moving in-house would enable me to do so. I really liked the variety and closeness to the businesses we worked with and wanted more of that in my career.

So I made the jump, and my first in-house role was at Speed Medical. However, it was becoming Head of Legal at AppSense a few years later that pulled me back into tech.

AppSense is also where I laid a lot of the foundations for Summize.

This sounds like another turning point?

It was. AppSense was a fast growth tech company with a global presence. They’d already hit $90 million in annual revenue by the time I joined.

I was only one year qualified so it was a big opportunity for me to establish and push the legal function from a standing start and really cut my teeth as an in-house lawyer.

AppSense is also hyper relevant to what I do now. It’s where I met my Summize co-founder and CDO, Dave Smith. It’s also where we met our Chairman and investor — who is the owner of AppSense — as well as our CFO.

Aside from the founding talent, is this also where the use cases for Summize originate?


At AppSense I was managing a large volume of contracts. I was creating, reviewing, and tracking them all day, every day and helping our business action and make sense of them.

We were looking at contracts from all angles, including diligence-type tasks such as red flag reviews, and had to create actionable summaries for contract lifecycle management purposes. We also had project-based and macro event-driven reviews.

All of this combined meant I had to review and action a wide variety of contracts and contract related use cases. Being a lean team and working so closely with the business, I got great exposure to the wider personas that work with contracts, which I found particularly helpful.

Given my interests in tech, and the fact that AppSense is a tech company, I was always hunting for ways to improve our process, standardize it and, if possible, use tech to automate or augment where appropriate.

I needed to scale legal as quickly and as robustly as possible while the wider business was growing.

This is really when I started to get interested in legaltech, and I would continually think about ways in which I could make the life of a GC — including my own — easier and more effective.

After the acquisition of AppSense by another company, I fancied a change and wanted to get back into another fast growth, early-stage business.

That led me to join Zuto, a car finance platform, and then later UserZoom, a platform used to plan, design and measure customer and user experience.

Why did I start a business? I think it’s a combination of the fact that I was both a potential user and also working with other users who needed to understand contracts for different business purposes. It was very inspiring working in fast-growth environments, scaling businesses and processes, both internally and with the products each business sold.

Eventually I caught the bug. You start to think… why can’t I have a go at this?

Between working at AppSense and Zuto, I’d been gradually scaling up my efforts to design and build Summize with a small team of AppSense alumni.

A bit like with sports and law, I then had to decide between two paths; carry on in-house or take a run at launching a business of my own.

What was the final tipping point, after which you decided to launch into Summize full time?

Interest and investment. We’d built prototypes of Summize and had iterated a lot of customer feedback — we were getting a lot of early buy-in. Very quickly we then started signing up users.

We went for investment, which we got, and that’s when it was time to push the button.

As we won investments and had customers lining up, we thought we needed to make a go of it, and grow a team. You can’t do that part-time.

How did your employer feel about the decision to leave and launch Summize?

I was always very open about the fact that I had this start-up that I was running on the side.

I’d also say I was actively encouraged. My employer loved having people working for them that were going to be future founders. They always had an encouraging approach — so long as you did your work and your side project didn’t detract from that, then it was no problem.

They were very helpful and encouraged me and my budding Summize team to ask questions, learn from colleagues and understand generally how to emulate what they had built in terms of starting and scaling a fast growing company.

There’s a number of lawyers who built businesses on the side around their day jobs and ultimately quit to make a go of it. Often they weren’t especially encouraged to do so, and in a few cases, quite limited in what they were allowed to do. Do you think law firms are missing a trick if they take a heavy hand to such entrepreneurial interests?

I do think it’s a risk. Obviously you don’t want lawyers who will be distracted from their work, or who will risk the reputation of the firm.

But law firms should take a keen interest in helping entrepreneurs who might later become a client. All the more so if the product they are building is something the law firm would derive value from, or could sell to clients.

One person who famously talks about the idea of hiring future founders is Peter Thiel, also a former lawyer (Sullivan & Cromwell). He was one of the founding members of PayPal and later an early investor in several unicorns, such as Facebook. Peter and the other founding members of PayPal, are today known as the PayPal Mafia for the fact that they’ve all gone on to found one or more unicorns.

Source: here

As a result, Peter Thiel talks a lot about intentionally hiring people into their last job, i.e. the last one before they go and found their own company. I think this is a great strategy.

What it means is that you hire people who are hungry and eager to learn and grow fast, and they take on greater responsibility and push boundaries.

If they then decide to leave and start their own business, you will undoubtedly have benefitted from a super-driven employee and potentially created a valuable node in your network.

We encourage the same at Summize. For example, one of our marketing team is currently building a successful clothing business via social media on the side. We love this creativity, and the entrepreneurial zest to find ways to grow and do things better.

If you can borrow these people before they go on to start their own business full time, it’s great.

Did your earlier experience working in tech companies influence how you think about Summize?

100%. Working in companies that promote innovation changes the way you think as a lawyer, and as a business person.

The idea of Kaizen sounds a little daunting but it’s really great. Everyone constantly looks for little ways to improve the business and every process. It’s a nice way to get everyone pulling together.

This has helped me and the Summize team find gaps in the market for contract tech.

Don’t get me wrong, there’s a ton of great vendors in the contract space. But we found a number of gaps in existing tech that we wanted to work with. Some of those gaps aren’t particularly tech related, but are more focused around customer experience.

There weren’t a huge number of tools that were super simple, easy-to-use, lightweight and cost-effective. That’s where we fit in.

Tell us about Summize. What problems does it solve and for whom?

We were founded in 2018 but didn’t officially launch with the current team until 2020.

The original idea focused around summarizing contracts for various business and legal purposes, most of which were inspired by my experiences and use cases as a GC.

What we offer today is a lightweight assistant for the contract lifecycle.

Summize is about supplementing not supplanting lawyer work. Our focus is on tackling marginal gains around typical legal tasks relating to contracts, and also similar contract related tasks relevant to other business users.

Our target clients are both law firms and in-house legal teams, and business users working with contracts on a day to day basis.

Are there any specific features you’d highlight?

We break down our use cases into pre and post-signature tasks.

For pre-signature, we provide a Microsoft Word Add-In, which allows users to quickly understand and navigate through key clauses. Key features include identification of defined terms throughout the contract and tight integration into our web platform.

Summize instantly creates a summary of any uploaded contract, no matter how unique. Those summaries can be edited and shared, and users can add comments and red flags.

Summize Contract Summary

Post-signature contracts make use of our web app. The web app provides a lightweight and easy-to-use contract management system, alongside quick and powerful contract summaries.

Like a lot of start-ups we’ve evolved our focus.

Originally we focused on due diligence and volume work, but have since zeroed in on being a lightweight, easy-to-use and easy to buy platform. Users can pick and choose each modular aspect of the product and slot it into their existing workflows where they see fit.

We’ve really tried to make the ‘try and buy process’ as frictionless as possible. That’s why users can sign-up for a free trial via our website.

It’s always better to let users try a product and see for themselves if it solves their need, rather than try and box them into a buying with endless demos and slideware.

Based on your experiences as an in-house counsel and as a founder, do you think the most impactful opportunity to transform legal is either big disruptive innovations or marginal gains driven by continuous improvement?

The latter. Transforming legal processes for the better, mostly involves standardising workflows and finding ways to add subtle automations or augmentations to the lawyer experience.

Most importantly, we need to work where the lawyers are already working and make the changes there.

Right now, legal is in a halfway house between being wedded to Microsoft Word and having an openness to exploring other contract editing platforms.

To meet lawyers where they already work, we’ve focused on making integrations to the systems they — and their clients — use everyday. That includes: a web app, a mobile app, a Word Add-In and integrations with Microsoft Teams.

As part of our customer on-boarding process, we adopt the Kaizen mentality. We help clients look for small improvements that they can stack up to create larger gains over time.

We suggest that the first thing they do is download the Microsoft Word Add-In to supercharge what they already do.

Why is that important for you and your customers?

For one thing, it lowers the change management overhead. Helping users get better at working where they already work is easier than trying to persuade users to adopt something entirely alien and unlike their existing or previous ways of working.

We are making it easier for lawyers and their business colleagues to collaborate. The latter don’t want to be dragged away to some lawyer specific platform that they only ever use when interfacing with lawyers — that’s literally the last thing they want to do.

Working with lawyers should be seamless and easy, not some process or system entirely removed from the way the wider business functions.

How do you see Microsoft 365 (formerly Office 365) impacting legaltech?

I don’t think that the future is some big, all-encompassing legal platform.

For one thing, the clients of lawyers — whether internal or external — won’t want to use some end-to-end legal platform for their day to day tasks, including those that interface with legal.

Instead they use Microsoft for the most part, or perhaps Google workspaces.

If you can build a product into the existing legal-business workflow that is already happening in and around Microsoft Teams, which can automate the manual processes and link together disparate data, you’ve probably increased your adoption significantly.

That is how the future of legal services evolves. The change will be around enhanced use of the tools users already have, not some paradigm shift to a legal specific omni platform that drags users away from their day-to-day tools.

Ultimately legal has to cater for the client, and the clients are all going over to that way of working.

What is the risk of ignoring this trend?

The more legal tries to create separate ecosystems, products and platforms away from where the business works, the more likely that it will alienate the end customer — the business users that buy legal services.

How, if at all, did having a professional sports career influence your business career?

It’s been hugely valuable.

The only difference between the top athletes is their mentality. Above a certain level, physical skill is no longer a predictor for success.

Of course there are the Ronaldos or the Messis of the world, but even then, they are only just a bit better physically than the next best player. What really sets them apart is their mental game. And that undoubtedly contributes to their physical game, whether it’s their confidence or drive to go the extra mile in training.

At one time, I was the European №1 Badminton player. During that time, I developed this sense of inevitability that I would win everytime I walked onto a court.

The way that I developed that was by training at 04:30am every morning. When I was training I knew that my competitors were asleep.

Sure, they were able to train more than me overall, but I took a lot of energy from the fact I was getting up super early to train, and I juggled more than they were juggling. And this grit and drive carried through into my career.

It used to frustrate me — and still does — when you see people who do the bare minimum, who aren’t obsessed with improvement and doing the best they can. Having the right mental game to commit and deliver each day on your goals builds your confidence and, in sports, your physical competence.

How do you apply some of these experiences and ideas to Summize?

We adopt the same ethos internally. However, we don’t expect everyone to be up at 4:30am!

One thing we do is to hold a meeting at five o’clock on a Friday called “1% better”. We know that every other team is probably clocking off for the week, happy with their performance… and in pre-covid times, perhaps down the pub.

Instead we are strategizing about how we can get 1% better next week.

We try to obsess over this.

We look into all the data we have about our processes and tweak tiny actionable things, measuring their impact: good, bad or indifferent to the overall process. Things that work, get repeated. Things that fail are removed.

As I say, it’s making consistent commitments to small, actionable changes each day and sticking with those that add value and removing those that detract value.

This is how you win in sport, and how you succeed in business.

Tom & Developers

Do you think the legal industry struggles with these sorts of ideas, such as Kaizen and marginal gains?

Yes, I think the biggest problem people have is that they’re looking for the silver bullets — the huge wins and instant fixes.

There’s almost this sense — said or unsaid — that there is some magic solution out there that dramatically, with little to no effort, transforms the legal function.

Weirdly there is also an ‘all or nothing’ mentality that is inherently conflicted. If tech X doesn’t entirely automate my job it’s no use, but at the same time, please don’t automate my job.

It’s an odd one.


What advice would you give to anyone thinking of entering the legal tech startup space from a legal background?

The first thing is to get into the mindset of just being creative day-to-day.

If you are a creative person and can look at a process, map it out, suggest improvements and involve yourself in a project, you will start learning the necessary skills to work in and around legaltech.

If you do a good job, those projects will start to find you as you become more experienced and knowledgeable.

Contributing to blogs, attending conferences, staying up to the date with the latest technology and volunteering to support legaltech companies can be great ways to gain the right experience.

If you keep your finger on the pulse, have an opinion and build that experience you will start to build connections.

Now is a great time to do that. A lot of legaltech businesses are still small enough where you can, if you ask in the right way and with enough persistence, open up connections and a knowledge base you wouldn’t otherwise have.

It also starts to get your name out there as being someone who is clued up and engaged.

Do you think being an entrepreneur is something you are or something you can become?

I believe that there’s no such thing as entrepreneurs, as such.

What you’ve got are people who are entrepreneurial thinkers and then you’ve got founders. To my mind this is a much more useful distinction. And I think that there’s a big difference between the two.

Having the mindset of thinking about everything you do and how it could be improved to find new value is being an entrepreneurial thinker. It’s that obsession with making things better and solving problems.

And then whether you become a founder or not is separate.

Whether you actually take the plunge, set up a corporate entity, go for investment or decide to be a CEO, is distinct from thinking entrepreneurially.

What is the hardest thing you’ve found about moving from practicing as a lawyer, into legaltech and being a founder. And what’s been the best thing about that?

The hardest thing has been to stop thinking like a lawyer.

As a founder and CEO, a lot of what you need to do is nothing like what a lawyer needs to do. As a CEO and founder, you need to set the vision, define the strategy and potentially push boundaries, whether that’s through cramming value into your product or driving sales.

And that’s when you can run into your inner lawyer.

That voice is more questioning, critical and asks questions like ‘is this too risky?’ or ‘is this the right thing to do at the right time?’ and so on.

That said, having been a lawyer, and working in and for software companies, I often replay some of the conversations I had in those roles. I try to get into the shoes of the lawyers and business users who have the problems Summize solves. This has been helpful throughout my time at Summize.

What’s the biggest difference between being a lawyer and a business person?

As a lawyer, you are mainly there to manage other people’s risks, and generally worry about their problems so they don’t have to.

You’re also a facilitator. You help the business do what they do best and ensure they do it safely and within the law or the parameters of the commercial contracts they sign up to.

As a business person, especially a CEO and founder, the emphasis is almost opposite.

It’s much more commercial. You have more latitude to take risks because the risks are ultimately your own to choose, not those of others to whom you are advising.

And you know what? It’s tough making that switch. You have to really change gears mentally and actively. But it’s incredibly fun. And very rewarding.

You go from being exclusively focused on downside risk as a lawyer, to being aware of that but ultimately looking for the upside opportunity. You start to see risk and reward as two sides of the same coin.

What are the most surprising and least surprising things you’ve experienced since starting a business?

The most surprising thing is that it feels like there’s a lot of lawyers who’ve gone into legaltech and founded a company or built a product.

However, despite this, so many products don’t capture the day-to-day life of a lawyer, and that of their colleagues in adjacent roles such as compliance, revenue assurance or sales, etc.

A lot of products are designed narrowly for a lawyer, but not for other and perhaps larger group of personas that also work with contracts. Again, I find that surprising. It seems a missed opportunity not to think more holistically.

There are also a lot of products throwing cool tech at problems without actually solving them.

In terms of what has been least surprising, and this is more of a personal one, but I thought the transition from GC to CEO would be a big one. I was ready for something ridiculously stressful. I was expecting to have those moments where you’re feeling up against it and thought it was going to be overwhelming.

So far it’s been anything but that. It’s been amazing. I love the engagement I have all the time with the product and the business, and the reward I get trying to inspire and build the team.

There’s a lot of transferable skills from GC to CEO.

I think if you take on a lot of responsibility as a GC in fast growing companies early in your career, you can build a really good set of skills and experiences that can make the shift to a leading business role a lot easier.

That said, you need to manage the mindset shift from being a problem solver — from a risk perspective as a lawyer — and instead become a better problem solver from an opportunity perspective as a business person.

If you have that set of experiences, the entrepreneurial mindset, the grit to be a founder and are able to change mindsets, you can switch from lawyering to being a CEO.

On the point of transferable skills, what do you think those are? We get asked this one a lot, including how to present skills learnt as a lawyer in a way that business people hiring you might best understand.

At Summize we have this series on creativity in law, and I think fundamentally what you are as a lawyer is a problem solver.

It’s a subjective area. It’s an area that requires opinion and interpretation of a set of facts from a contract or a situation. In many cases, you need to complete that process very quickly and accurately appraise a course of action, based on the information to hand.

You get good at making risk weighted decisions. You also develop a keen eye for issue spotting and identifying dependencies. This is definitely something non-legal professionals sometimes lack.

The best lawyers are also particularly good at discounting edge cases and focusing on the red flags and moving the business along without being the ‘department of no’. ‘Being commercial’ is the other way of describing this skillset.

That doesn’t mean you constantly throw caution to the wind and ignore risk as a ‘yes-person’ to the business. But you understand the business, it’s drivers and what is and isn’t important in the grand scheme of things.

Clients value lawyers who master the business and understand perspective. Good lawyers help navigate stormy or fair seas, and only steer ships back to shore if absolutely necessary and not every time a cloud appears on the horizon.

As a lawyer you get good at crunching a lot of variables, analysing them and providing coherent specific advice to solve problems. And I think when you are a CEO, or as a leader in a business, you need to apply similar skills, albeit for a different purpose.

I think if lawyers adopt these more entrepreneurial and commercial qualities, and pair them with an understanding of process improvement philosophies such as Kaizen, it could be game changing.

Right now legal remains tied to precedent, whether it’s what course of action to take, or how to draft a document, or how to send an email. Falling back on ‘this is the way we’ve always done it’ without pausing to zoom out and ask ‘is this the way we should be doing it?’ would unlock so much value for lawyers and their clients.

You’re obviously big on personal development and continuous improvement, both for business but also at the individual level. Do you have any advice about this subject?

Never sacrifice personal development. Never sacrifice learning or investing in yourself.

I say this because I did sacrifice personal development at different times. And I’ve always regretted it. Thankfully, I reprioritized how I think about things and make sure that personal development is something I no longer sacrifice.

After working in so many tech companies, I was taken aback at how much everyone put into their personal development; listening to podcasts, reading books, experimenting with new ideas. So I listened and learnt and figured out what interested me, and made a point of cramming personal development into my commute and spare time.

This massively changed my entire outlook and gave me the drive to start a business and pull together the various threads of my career into a new direction.

It made a big difference to how I went about my job and my interactions with colleagues.

Would you recommend any books or other media that have helped you or that you found interesting?

I’d recommend the following:

  • The Spirit of Kaizen by Robert Maurer. Maurer is on the faculty of the UCLA and University of Washington Schools of Medicine, and a proponent of evidence-based psychology into practical strategies for success. The book contains a wealth of simple but powerful techniques that can be applied to almost any workplace situation; especially when you’re trying to navigate radical change, high-pressure deadlines, and competition. These are the same methods of small, continual improvement that have been tested by the largest companies, such as Boeing, Toyota, and the U.S. Navy.
  • Atomic Habits by James Clear. This book is centered around debunking the prevailing wisdom that you need to think big to change. His book explains how big change comes from the compound effect of hundreds of small decisions: from doing two push-ups a day, waking up five minutes earlier each day, or holding a single short phone call. An excellent and practical book for creating change and great habits, whether individually or beyond.
  • Sapiens by Yuval Noah Harari. This book is really insightful in terms of how society has developed. Perhaps I’m biased given my fondness for Kaizen, but the book has a definite thread of continuous improvement theory when assessing how societies rise and fall and evolve and manage change. Really eye-opening!

Interested in legaltech careers like Tom’s?

See here for our legaltech careers guide for advice and tips on the roles, organisations and routes into legaltech.

Originally published at lawtomated.




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