Alistair Vigier is an entrepreneur who spent seven years serving in the Canadian military before leading legal technology ventures that challenge the legal industry: resilience, bold decisions, and a clear vision for the future mark his journey.
As the CEO of Caseway, a company that transforms legal research and contract review with artificial intelligence, Alistair Vigier has faced both controversy and success. In this interview, he opens up about the lessons from his military service, the highs and lows of his time at Clearway, and the ambitious mission driving his new company, Caseway, forward.
Alistair Vigier: My time in the military was pivotal. It’s where I learned what it means to operate under pressure and to never back down from a challenge. I spent seven years in the army, and those experiences built a foundation for everything I’ve done since. The military teaches you discipline, but also how to adapt when the plan falls apart, which happens frequently in both the field and in business.
One thing I took away from my service was the importance of having a clear mission. In the military, you can’t afford to be vague about what you’re trying to accomplish because lives are on the line. In business, I’ve tried to maintain that same sense of clarity. Whether developing a product or negotiating with partners, we focus on the end goal and ensure everyone on the team understands their role.
Alistair Vigier: Clearway was a rollercoaster. On the one hand, it was a groundbreaking platform that connected lawyers with clients in a way ahead of its time. We put 1.3 million lawyers on the platform, and that scale taught me a lot about how to grow a technology company. I’m proud of what we achieved there, especially in giving people easier access to legal help. There were also over 20,000 lawyer reviews on the website when I left Clearway.
But like any ambitious project, there were challenges. Internally, we faced disagreements about the company's direction. I wanted to lean more into machine learning and automation, while others focused on traditional growth strategies. Those differing visions eventually led to my decision to step away, at least for now. Walking away wasn’t easy, but it allowed me to double down on what I believed in: using artificial intelligence to change how people interact with the legal system fundamentally.
Clearway wasn’t perfect, and I think it’s important to own that. There were controversies, but there were also real lessons in managing a technology company. Those lessons became invaluable when I launched Caseway.
Alistair Vigier: The lawsuit was a pivotal moment for Caseway. When trying to disrupt an industry as entrenched as the legal one, you’re bound to ruffle some feathers. The lawsuit was essentially about access. The legal question was whether legal data should be open to innovation or locked down by traditional players. We believed (and still think) that making legal information more accessible benefits everyone: lawyers, clients, and even the courts themselves.
Winning the lawsuit would be a win for innovation in the legal space. It would affirm that companies like Caseway have the right to push boundaries and challenge the status quo. Legal battles are financially and emotionally draining, but they can also be clarifying. The lawsuit prompted us to redouble our efforts to democratize access to legal tools and data.
It also allowed us to appear in the media frequently to share our story. We have over 2700 people using Caseway.
We also passed a data audit, which showed that we didn’t use any of Canlii's work product. As far as I know, I believe the lawsuit is over.
Alistair Vigier: Caseway is about speed and accessibility. We’re processing over a hundred million court decisions in seconds, which saves lawyers and non-lawyers countless hours of research. It’s about giving people intuitive and actionable tools. Legal technology products are often overly complicated, and lawyers don’t have time to figure out clunky interfaces or endless features they’ll never use. We are the best AI at the best price, available for only $49 per month.
Another key differentiator is our contract review feature. Caseway doesn’t just analyze contracts; it checks them against court decisions to flag potential risks. That’s a game-changer because it allows lawyers to create more substantial agreements without poring over case law for hours. We’re also working on integrations with platforms like Affinipay and The Digital Journal, which expands our reach and make it easier for firms to adopt our tools.
Alistair Vigier: If you’re not shaking things up, you’re probably not making much of an impact. Controversy doesn’t scare me. It’s usually a sign that you’re doing something different, and “different” is what industries like legal desperately need. I don’t go out of my way to create friction. It’s more about staying true to the mission and not being afraid to stand up for what you believe in, even if it’s unpopular. I don’t mind standing up against bullies.
I believe my military background also plays a role here. In the army, you learn that not everyone will like you or agree with your decisions, but that can’t stop you from moving forward. You must focus on the bigger picture and trust that your work will speak for itself over time.
Alistair Vigier: The growth comes down to solving real problems and listening to our users. Lawyers are overwhelmed by paperwork, case law, and administrative tasks. Caseway cuts through that noise and gives them actionable results. When you make someone’s job easier, they will tell their colleagues about it; that kind of word-of-mouth has been huge for us.
We’ve also been fortunate to secure strong partnerships. Our collaboration with Affinipay, for instance, has been a significant success. They’re a large company with a massive user base, and the fact that they see value in what we’re doing validates our approach. We’ve also had success with government contracts and large firms, which has helped us scale more quickly than I initially expected.
Q: How do you handle the pressure of running a fast-growing company?
Alistair Vigier: Honestly, pressure is part of the job. You probably shouldn’t be leading a company if you're uncomfortable with it. For me, it’s about staying grounded. I have a great team at Caseway, which makes a difference. I trust them to handle the day-to-day so I can focus on the bigger picture.
I also make a point of stepping back when necessary. Those moments of disconnect are crucial, whether it’s spending time with my family or just going for a hike in the Vancouver North Shore mountains. They give me the perspective to make better decisions when I’m back in the thick of things.
Alistair Vigier: Balance is tricky, and I won’t pretend I’ve got it all figured out. However, I’ve learned that being present goes a long way, even in the smallest moments. My wife is incredibly supportive, and we make a conscious effort to carve out time for each other, even during the busiest weeks. We’re also expecting a child soon, so that will add a whole new layer to the mix. It’s exciting, but it also motivates me to build something valuable that will make the future better for my child.
Alistair Vigier: I see Caseway as a standard tool for lawyers worldwide. The legal industry is ripe for transformation, and we’re just scratching the surface of what’s possible with machine learning and automation. I also want Caseway to be a company that lawyers and self-represented people trust, not just for its technology, but for its commitment to making their lives easier and their practices more effective.
On a personal level, I hope to see Caseway leading the charge in making legal services more accessible for lawyers and their clients. It’s all about impact. If we can make the legal system faster, fairer, and more efficient, I’ll consider that a success.
