THOMAS HAMILTON / From Bay Street to IBM's ROSS Intelligence

Check out Tom on Twitter @tjhammy, or view his LinkedIn profile here.


Thomas both summered and articled at the Toronto office of Dentons, and following articling received an offer to return as an associate in the corporate group in the fall of 2015. While articling in 2014, he had volunteered some time to help a friend of his by speaking to some of his co-workers about Big Law, who were involved in a really cool legal technology project. Their company was ROSS Intelligence, and they were working alongside IBM on a project which harnessed the power of artificial intelligence aimed at legal research.

As the company began to take off, they approached Thomas about delaying his start as an associate by a year to work with them in California. He fell in love with the job, and never went back. 

Tom is VP Strategic Partnerships for the ROSS Intelligence project, a legal research AI built on IBM's Watson.

Tom is VP Strategic Partnerships for the ROSS Intelligence project, a legal research AI built on IBM's Watson.

Let’s start with the basics. Did you always imagine yourself going to law school?

Nope. Growing up I had loved Orwell and wanted to be a writer. I was accepted into an arts high school across town. From there, my interest in society and morality continued to develop, and I became very focused on the idea of international development, like a lot of people in our generation. I think it was while studying the classics in Halifax that my interest in law began to form.

Law school ended up being a way for me to reconcile a lot of different interests I had in one setting [while ensuring that my older sister couldn't one up me by being the only lawyer in the family ;)]. From there, McGill was an obvious choice for its bi-juridical program and excellent reputation.

Also, ever since reading Barney's Version I had really wanted to live in Montreal.

What makes your career lawfully uncommon at ROSS Intelligence? Maybe give us a quick breakdown of what your role is there?

I'm VP Strategic Partnerships at ROSS Intelligence. I work hand in hand with our legal team to oversee all of the training of ROSS, while also working alongside our partner firms to ensure that ROSS is providing as much value as possible at all times to our end users.

I also work closely with the technical team as they continue to develop ROSS's capabilities (just wait till you see some of the stuff we'll be coming out with soon!).

It has been an enormous privilege to be directly involved in the development of artificial intelligence software which will both democratize and fundamentally alter how we interact with the law.

A ROSS Intelligence team photo (minus ROSS!)

A ROSS Intelligence team photo (minus ROSS!)

At what moment did you realize that you wanted to switch gears? At what moment did you realize that you wanted to do law your own way?

Dentons was an excellent firm to have articled with, and from the first day of summering to the last day of my articles, I received terrific mentorship from the lawyers in the Toronto office, and was exposed to interesting and varied work. There was no dramatic "ah-ha" moment for me, it was more that I was presented with an incredible opportunity to do work that was going to change the industry I had started in, and was fortunate enough to have the support I needed from my mentors at the firm, along with family and friends, to make the leap.

Were you always interested in start-ups, robotics and law? Or do you feel like you fell into it?

I hadn't expected to go into business, but once I started to study it as a way to gain useful skills for development work, I found myself very interested in it. From there, I think my interest in start-ups was just the next logical step, and a legal startup with my background makes a lot of sense.

Additionally, both my parents made career changes when I was young and left behind established positions to work as consultants out of our home, so from a young age I grew up around the concept of working for yourself.

What got your juices flowing or tickled your fancy while at law school? What made your blood boil or made you snooze while at law school?

I loved the bi-juridical program at McGill, as challenging as it may have made some of our 1L classes. :)

I think the exposure we had from the onset of our education to multiple judicial traditions - as well as additional legal traditions once I was able to branch out in more advanced classes, was a major differentiating factor for me while articling, and something which continues to help me to this day.

In terms of anyone's blood boiling, I very vividly remember being trained on legal research software in the computer lab and just being blown away that there wasn't a more efficient way to do it.

Tom's best friend from McGill Law (left), laughing and carefree. Tom (right) dreads the impending 1L moot.

Tom's best friend from McGill Law (left), laughing and carefree. Tom (right) dreads the impending 1L moot.

Do you see law all around you at Ross Intelligence? Does this differ from your previous role at Denton’s?

Yes to the first question, no to the second!

You are at a coffee house speaking to a first year law student. What advice would you give them? What advice would Ross, the Legal Robot, give them?

Thomas Hamilton's advice to 1L students: "Have fun, make friends, stay open minded and curious and try your best to get a good GPA."

ROSS's advice to 1L students: "Have fun, make friends, stay open minded and curious and try your best to get a good GPA."

What does a day in the life of Tom look like? What will a day in the life of ROSS, the Legal Robot, look like?

A day in the life of Tom is very busy, and full of fun challenges. It starts early, and ends late. I'm fortunate to work with an extremely talented and hard working group of individuals, who are every bit as excited by our mission to democratize the law as I am, which makes every day at work a blessing.

A day in the life of ROSS involves a whole lot of studying, followed by spurts of calmly and confidently providing very accurate results in very little time to attorneys all over the United States.

If you were given the blessing and curse of an extra hour every day to do whatever you wanted, what would it be?

Definitely reading.

Any regrets? (Yeah, we are retrospective like that).

In my career, zero.

While at McGill, I wish I had eaten substantially more Schwartz's.