There’s a particular kind of pressure that comes with being a legal technologist in a global law firm. You’re caught between two worlds: the traditional pull of billable hours and client service, and the forward-looking promise of innovation and efficiency. Hugo Cassidy, a partner at Pinsent Masons, knows this tension intimately. But unlike many in his position, he’s found a way to navigate it – by speaking the language both worlds understand: return on investment.

“I’m quite a weird creature in law,” Hugo admits at the start of our podcast episode. It’s a statement that immediately captures something essential about the current state of legal innovation. What should be routine – measuring the value of technology investments – still feels unusual in an industry built on precedent and tradition.

Hugo’s journey into this hybrid role wasn’t planned. He started as a leveraged finance lawyer, spending a decade working on complex international financings. “Legatics would have been great when I was working on those transactions,” he reflects, “but it was before that time.” After moving into regulatory technology work on ring-fencing projects for major banks, he discovered something that would reshape his career: the combination of legal expertise and technology leads to highly effective solutions.

For the past six years at Pinsent Masons, Hugo has dedicated himself entirely to what he calls “tech-led and tech-enhanced delivery services.” It’s a role that would have been nearly impossible to justify a decade ago. Today, it’s become essential.

The commercial reality

What’s changed? The answer lies partly in how clients now value legal services. Hugo describes a fundamental shift in the firm’s approach: “Six years ago, our technologists would have been seen as back office – now I regularly work with our technologists on our tech services side, and we’ll be in client meetings together.”

This isn’t just symbolic. It reflects a deeper truth about where value is created in modern legal work. “I’m working on a project at the moment where actually the star of the show often is the technologist,” Hugo explains, “because they’re the person who’s dealing with the knotty problems of how we’re designing and building this app.”

The implications are striking. Technologists, who were once considered back office and not chargeable to client matters, are regularly working alongside lawyers in client meetings, pitching, building, and delivering projects. In fact, technologists are now seen as critical members of the delivery team, reflecting a significant shift in how legal value is defined and delivered.

The ROI challenge

But enthusiasm and anecdotes aren’t enough when you’re asking senior management to approve significant technology investments. This is where Hugo’s approach becomes particularly instructive. He divides his technology work into two distinct categories, each requiring different ROI considerations.

The first pillar, what he calls “sophisticated solution design”, involves building bespoke technology for specific projects. These are the big-ticket items: remediation projects, large-scale re-papering exercises, custom applications. “You spend a lot of money and effort to design the process, configure certain technology, roll it out, and then wind it down and decommission,” Hugo explains.

For these projects, the ROI calculation is brutally direct. “Sometimes I have to restrain myself because it’s unsatisfying to build something that’s a little basic – you know, it could be better – but actually, if there isn’t the money that’s coming back or the value that it’s generating, you have to go, ‘This is good enough.’ And that’s a good conversation to have, and to recognise that.”

The second pillar focuses on “process enhancement or transformation” – systemic changes to how legal work gets done. This might include document automation, transaction management platforms, or workflow tools that will be used repeatedly across multiple matters. Here, the ROI story becomes more compelling. “It’s all about ROI,” Hugo states plainly. “If we do this, how much money is it going to save, typically calculated through full time employee hours that are no longer spent on that activity.”

The math can be straightforward: “Rule of thumb, if you’re going to do a doc auto project, you’re automating one document, it’s of medium complexity, you’re typically going to save 50-75% time compared to a manual completion of that document to that first draft up and running.” On a recent engagement, Hugo presented the business case simply: “We will cut the cost of production for your template by half, and this will pay you back in six or seven iterations. After that, you’re in the money.”

The science of comparison

But measuring ROI in legal work isn’t as simple as running a controlled experiment. Hugo draws an analogy to high school science: “If you want to measure the impact of something, you run an experiment and then you change that one thing and everything stays the same – temperature, light, the amounts you’re using.”

The problem? Legal transactions resist this kind of isolation. “There’s a myriad of factors that are going to affect how much it costs to deliver,” Hugo notes, “ranging from who the people are on the transaction. What’s their style? Are they quite argumentative? Are they going to make difficult points out of stuff that you’re always going to get to the same outcome on? How international is it? How many countries are involved? How many lenders are there, how many borrowers…”

Pinsent Masons’ solution was to think bigger. Rather than comparing individual transactions, they examined larger data sets – matters that used technology versus those that didn’t – while narrowing down variables like jurisdiction, parties, and transaction type. “We found that to be instructive, but it is not straightforward,” Hugo admits, “because even law firms, which are getting better at gathering data, may not have all the interesting variables for a transaction that might make it a bit more expensive or a bit cheaper.”

This approach requires both sophistication and realism. The data must be robust enough to demonstrate value, but the analysis must acknowledge its limitations. For firms just beginning their ROI journey, Hugo suggests starting with structured pilots: “Use structured questionnaires to gather structured data. Giving people a free text box to fill out is time consuming, might never happen, and you’re going to get back data that is going to be quite hard to analyze at scale.”

Beyond the spreadsheet

Yet for all this focus on quantitative analysis, Hugo is adamant that numbers don’t tell the whole story. “The qualitative feel can be dismissed from people who are obsessed about trying to find a monetary ROI,” he observes, “but being in the industry, it’s hugely important.”

He shares an example: using Legatics for a template update exercise with a client. “The best fit was Legatics for this project, and the client loved it. It’s not like we had priced it in and we didn’t work out whether it made any difference, but the client absolutely loved the way in which they were able to keep track of everything.”

The qualitative benefits extend to lawyer wellbeing too. “As a partner, I’m often working across a number of transactions and need to stay on top of where we are on those and where the document is that does this,” Hugo explains. “Something like Legatics, for me, is completely invaluable because it allows me to hop between matters easily, see where everything is, see where the statuses are.”

This touches on something fundamental about technology adoption in law firms: the human experience matters. Technology that lawyers actually want to use—that makes their lives better, not just more efficient—creates value that’s difficult to quantify but impossible to ignore.

The cultural dimension

Perhaps the most revealing part of our conversation centers on language. Hugo notes that even simple word choices can profoundly shape how people think and interact – a concept known as cognitive linguistics. He’s become especially aware of how firms talk about their people. “Typically, people in law firms refer to lawyers or non-lawyers, as in, there’s our expertise, and then there’s everyone else who’s in this sort of bucket. I’m really keen not to use that because I think, from a cognitive linguistic perspective, it’s really unhelpful.”

Instead, he advocates for terms like “fee earners” that include both lawyers and technologists. “The words you choose will inform the way you think about stuff,” he argues. This isn’t just about being inclusive – it’s about recognizing where value actually comes from in modern legal service delivery.

The implications are practical. When firms write off “non-lawyer” time first during billing disputes, they’re distorting their true cost of production. “It’s very distorting to ignore a cost of production which might be really material,” Hugo points out. “You might go, ‘Actually, goodness, now we’ve taken that into account, this matter that we thought was fantastically commercially viable is not at all.'”

This speaks to a broader truth: firms that think of themselves as truly multidisciplinary businesses – rather than lawyer-led organizations with support staff – make better strategic decisions. They measure what matters. They value all contributors appropriately. They run their practices like businesses.

The path forward

For Hugo, success in driving technology adoption comes down to three things: senior stakeholder buy-in, rigorous measurement, and sustained energy.

On the first point, he is emphatic: “It does require a lot of energy to get something adopted, particularly within the law firm, because it requires behavioral change, investment, comms. It rarely happens just by itself.” Having partners who visibly champion technology—who show up to training sessions, who reference it in client meetings—sends a powerful signal to junior lawyers about what the firm values.

On measurement, the goal isn’t perfection but progress. Start with pilots in appropriate practice areas. Gather structured feedback. Build business cases that acknowledge both quantitative savings and qualitative improvements. “The further a story goes from the source, the less the qualitative aspect carries through,” Hugo notes. “But numbers are the same regardless of how many hands they have passed through.”

And on sustained energy, Hugo recognizes that adoption is never finished. Each new cohort of lawyers needs training. Each new practice area requires champions. Each quarter brings new questions about value and investment. “Marketing is so important,” he emphasizes, describing the ongoing need to promote successful implementations internally.

What it all means

Our conversation with Hugo reveals something important about the current moment in legal technology. We’re past the point where firms can succeed simply by having advanced technology. The differentiator now is the ability to deploy technology effectively – to prove its value, to drive adoption, to integrate it into how work actually gets done.

This requires people like Hugo: lawyers who understand technology, technologists who understand legal work, and business thinkers who can bridge both worlds. “I don’t know if you guys have seen examples of that where a pilot or a trial has been attempted, but it hasn’t really got any traction, and it’s kind of just fizzled out,” Hugo asks toward the end of our conversation. The answer, of course, is yes.

But the firms that succeed aren’t necessarily the ones with the best technology. They’re the ones with the clearest thinking about value, the strongest commitment to measurement, and the cultural willingness to treat technology professionals as equals in the delivery of legal services.

Pinsent Masons’ structured approach to ROI – balancing hard data with human experience, short-term costs with long-term value – offers a roadmap for other firms. It’s not easy. It requires investment in data infrastructure, commitment from leadership, and the courage to change how work has always been done.

But as Hugo’s role demonstrates, it’s also increasingly necessary. The question isn’t whether law firms will need to prove the value of their technology investments. It’s whether they’ll do so rigorously enough to make good decisions, quickly enough to stay competitive, and honestly enough to know when they’re getting it right.

“If you were starting a law firm, or you were running a law firm, and you hadn’t started making forays into transaction management software, generative AI, doc auto,” Hugo poses, “you’re going to be at a huge competitive disadvantage.” Not because the technology itself is a magic bullet, but because it represents a different way of thinking about value, capability, and what modern legal service delivery actually means.

The future of legal practice won’t be determined by who has the most technology. It will be determined by who understands it best, deploys it most effectively, and measures its impact most rigorously. That’s the real return on investment—and Hugo Cassidy is helping to show the way.

This conversation is from the Cracking Legal Innovation podcast – listen to the full episode for more insights on legal technology ROI, innovation strategy, and the transformation of legal services. Subscribe to Cracking Legal Innovation on Apple Podcasts, Spotify, or wherever you get your podcasts.

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