Alistair Vigier isn’t your typical technology founder. From his seven years serving in the military to leading legal tech ventures that challenge the legal industry, his journey is marked by resilience, bold decisions, and a clear vision for the future. 

As the CEO of Caseway, a company transforming legal research and contract review with artificial intelligence, Alistair Vigier has faced 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.

Q: Alistair, let’s start with your time in the military. It’s not a background we often see in the tech world. How did your service shape you as a leader?

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 a lot 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.

Q: Before founding Caseway, you ran Clearway Law. It had its fair share of successes and controversies. Can you talk about that experience?

Alistair Vigier: Clearway was a rollercoaster. On one hand, it was a groundbreaking platform—connecting 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 tech 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 direction of the company. 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.

Q: Caseway has been in the spotlight recently, including the lawsuit against CanLII. What can you tell us about that?

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—whether legal data should be open to innovation or locked down by traditional players. We believed (and still believe) 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 made us double down on our mission to democratize access to legal tools and data.

It also allowed us to get in the media often to tell our story. We have over 1000 people using Caseway.

Q: You’ve touched on Caseway’s mission. Can you elaborate on what sets it apart from other legal tech companies?

Alistair Vigier: Caseway is about speed and accessibility. We’re processing millions of court decisions in seconds, which saves lawyers countless hours of research. It’s about giving people intuitive and actionable tools. Legal tech 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, at only $49/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 pouring over case law for hours. We’re also working on integrations with platforms like Clio and MyCase, which expands our reach and makes it easier for firms to adopt our tools.

Q: Some might say you’ve gone from one controversial project to another. Does that ever weigh on you?

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 think my military background plays a role here, too. 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.

Q: Let’s talk successes. Caseway seems to be growing fast. What’s driving that growth?

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 Clio, for example, has been a big win. They’re a $4 billion 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 I need to. Those moments of disconnect are crucial, whether it’s spending time with my family or just going for a hike. They give me the perspective to make better decisions when I’m back in the thick of things.

Q: You’ve mentioned family. How do you balance your personal life with running a company?

Alistair Vigier: Balance is tricky, and I won’t pretend I’ve got it all figured out. But I’ve learned that being present goes a long way, even in small moments. My wife is incredibly supportive, and we consciously try 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.

Q: Looking ahead, where do you see Caseway in five years?

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.

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