A Big Law Convert to Legaltech

June 20, 2017

Following a recent presentation I gave at a partners’ retreat, I was encouraged to share the story of how I came to work in legaltech, as well as some of my thoughts on the development of artificial intelligence (AI) with a broader audience.

Dovetailing well with my (sort of failed) New Year’s resolution to do more writing, I decided to commemorate the two year anniversary of my departure from Big Law by putting my thoughts into writing.

How it all started

I began law school at McGill University in the fall of 2010. From there, I opted for the typical career in corporate law and took a position with Dentons in Toronto, their largest office in Canada. It was while focusing in corporate commercial law at the firm, competing to get enough experience to receive a permanent offer, that I got to know the team at ROSS Intelligence.

Although skeptical of the legal technology field at first, I fell in love with ROSS Intelligence’s mission to revolutionize the law through AI. After receiving a permanent offer from Dentons’ corporate group, I was given the summer off to regroup and travel before beginning my contract in September. By now, I’d already been invited down to spend the summer with the ROSS team as they worked with Y Combinator in Mountain View, so I took the red pill and traded in my suit and tie for a hoodie and flip-flops.

A Big Law Convert to Legaltech Thomas Hamilton

As soon as I landed, I fell completely in love with the project, and never ended up making it back to the firm. As they say, the rest is history. I even left my clothes and furniture at a friend’s place in Toronto where most of it still is — I think.

There have been many changes in my life in the past 2 years, but they have really just been a reflection of the changes occurring across the legal industry as a whole. Below I list the four big changes I’ve already seen unfold, which I hope you’ll enjoy reading (and debating) as much as I’ve enjoyed writing about them.

Law firms now care (at least a bit) about technology: Whether the result of client pressure (more on that below), shifting priorities among senior firm leadership, or as a lagging indicator of a general trend among professions, law firms are now open to conversations about the widespread adoption of new technology.

In my time at ROSS Intelligence I have observed first-hand the different ways in which technology is adopted and used by different types of lawyers. Unsurprisingly, organizations with purely access-to-justice related mandates are the most willing to adopt new technology into their workflows. This is part of a simple calculus. Better technology allows them to bring better legal aid, to more people, more quickly. It has been one of the most rewarding moments of my career to witness the empowerment of these access-to-justice organizations through their use of ROSS and other legaltech solutions.

Thankfully, the current generation of legaltech is now beyond this first stage of adoption and is being accepted into private practice. This is occurring not only among sole practitioners and boutiques, but also among full service law firms — from the regional powerhouses to the super-international mega firms — that have until recently been conservative hold-outs. Building a product which is already being actively used in law firms has been one of our greatest accomplishments at ROSS Intelligence, although there is still much work to be done in this market.

Clients and in-house departments are now forcing legaltech adoption

The shifts in client demand which were just beginning when I entered law school are now in full swing. Clients are expecting more from lawyers, for less money.

Simultaneously, in-house departments continue to become larger and more sophisticated. When external counsel remains uninterested in legaltech innovation, their blue-chip clients are increasingly forcing this dialogue. This is fundamentally changing expectations of the role external counsel should play, and of what it means to even be a lawyer.

Which brings me to the most important point about the future of our profession.

The makeup of law schools is changing

By the standards of the legal industry, I am a recent law school graduate, but when I visit law schools I feel like a dinosaur.

The majority of my peers applied to law school in 2009 as a shelter from strange economic forces which their History and Political Science majors hadn’t prepared them to understand. We were collectively aware that something bad had happened and that the prestigious and exciting opportunities our upper classmates had graduated into wouldn’t exist for us immediately upon graduation. Law school was a shelter from the storm, and an arts student’s dream — a guaranteed ticket into the upper middle class, through a prestigious, cerebral profession that had gone largely unchanged for the last 500 years.

The law applicant of 2017 is not interested in these things. They are painfully aware of both the over-supply of lawyers, and of the reduced prospects of finding employment following graduation. They know that the likelihood of obtaining partnership through the traditional model continues to decrease, and that the cozy boys club is now vulnerable to purges of downsizing and demoting equity partners.

A Big Law Convert to Legaltech Thomas Hamilton

Despite all of the above, they still apply, because their priorities and backgrounds have changed. When I think of my 1L class at McGill, I can think of exactly zero classmates who came from a computer science background. While I had studied the classics, I had majored in finance, and was considered an outlier for having done so.

Yet when I visit law schools now to speak about my work with ROSS, I am asked by students what coding languages they should study, and what strategies they should employ for using artificial intelligence in their practice. Today’s students are applying to elite law schools with no intention of pursuing the typical legal careers we signed onto. These are students who are interested in starting their own companies to shape the law through technology. They are also students who will eschew the brass ring for employment with the new breed of in-house departments that not only reward but also celebrate technological innovation.

A similar phenomenon is playing out in legal academia. While there will always be opportunities for pure legal theorists, especially at the most elite and established law faculties, there is an increasing willingness among the academic community to not only train their students on the use of technology in the classroom, but also participate directly in the development of this technology, often in an interdisciplinary relationship with other faculties (for example, the work we’re doing with Duke Law). This is directly related to growing demand by students to have greater cross-disciplinary and tech focused exposure in law school.

AI is here to stay

In line with the above changes, since arriving in Silicon Valley I’ve seen a dramatic shift in attitudes towards AI. Where in 2015 it was a niche subject discussed only in tech circles, it has now become not only accepted into the mainstream, but is also sweeping across legal technology. AI has become the catalyst that has finally made the new wave of legaltech commercially viable. It has already transformed medicine and finance (and will surely continue to do so), and is now making major inroads into the law as well.

While AI detractors still exist in the ranks of Big Law, I have witnessed their criticisms disappear one by one. Legaltech and AI technologies are being embraced by the most tech-forward from the AM Law 100 to solo-practitioners, and this trend will only accelerate. This is a space that will continue to become more and more populated with exciting players, further increasing the options available for each of the groups discussed above to enhance and refine their work processes.


While the law as a profession will never disappear, law as an industry looks very different from two years ago. It has been an absolute pleasure to be welcomed into the legaltech community with such open arms, both as a former Big Law lawyer but also as the first employee of an AI company throwing it’s hat into the legaltech ring. I’d like to thank all the friends I’ve made in the legaltech space over the past two years. With the arrival of blockchain, smart contracts, self-driving cars and even more around the corner, it’s anyone’s guess how the next two years will turn out but one thing is for sure, the importance of AI and legaltech in our profession is here to stay…

A Big Law Convert to Legaltech Thomas Hamilton

… and I’m happy I took the red pill

Thomas Hamilton helps co-ordinate efforts across the company to ensure that sole practitioners, legal aid groups, law firms, state bar associations and law faculties get as much value out of ROSS as possible.

Prior to joining the ROSS Intelligence team Thomas was a lawyer at the Toronto office of Dentons. He speaks in both the United States and abroad on legal technology innovation and law firm strategy, and believes passionately in the ability of artificial intelligence to improve access to justice worldwide.