Welcome to the latest installment in our ongoing series of getting to know the DeepJudge team.
Meet Tony Ensigner, SVP of Sales at DeepJudge. Having been a pivotal member of the teams at Practical Law, Intelligize, Kira, and Casetext, Tony’s track record is beyond compare. He has played a direct role in shaping modern LegalTech. More than just a front-row witness to law firm innovation, he has been a driving force behind multiple waves of change. What sets Tony apart is his deep empathy for customers and a keen understanding of their challenges—qualities that go beyond the typical sales role. Raised in a hardworking small town, he carries with him both a relentless work ethic and a refreshing humility, making him not just a leader, but a true partner to those he works with.
Join us as we learn more about the people behind DeepJudge.
Where did you grow up and how did you get first interested in legal technology?
I grew up in Hannibal—a small town in southeast Ohio with ~300 people. I was surrounded by incredibly hardworking folks, many of whom labored in coal mines, steel mills, and on farms. I wouldn’t trade growing up in that environment for anything—it really instilled in me the value of hard work and practical solutions. My journey into legal tech began at Wolters Kluwer, where I started on the support desk helping customers with software for SEC filings. That first taste of using technology to simplify complex tasks hooked me, and I’ve been passionate about making work lives easier ever since.
What did you focus on in school?
I studied Computer Information Systems, which gave me a solid technical background. It was the perfect mix of theory and practical skills that set me up nicely for roles that blend tech with real-world problem solving.
What is your favorite part of working with the team at DeepJudge?
I love working with the founders—Paulina, Yannic, and Kevin—and seeing how we all bring something unique to the table. At DeepJudge, it’s not just about tackling the challenge of helping firms access their internal knowledge without the manual hassle; it’s also about building an amazing culture where everyone, across all departments, is rowing in the same direction. That shared focus really lets legal pros concentrate on what they do best, and it makes the whole journey incredibly rewarding.
What is a surprising or fun fact that people might not know about you?
A fun tidbit about my journey: I started my career on the support desk helping customers, then moved on to be part of the first US sales team at Practical Law. It’s been a wild ride being part of early-stage startups like Intelligize and Kira, and most recently, Casetext—where I had the opportunity to work with an amazing executive team and help pioneer GenAI into the legal vertical.
When you’re not working what do you do to unwind?
When I’m off the clock, I love hanging out with my kids and our two energetic Australian Shepherds. Whether it’s running, doing triathlons (often with the dogs tagging along), or simply enjoying some family time, I’m always on the move. I also have a passion for cooking—a skill I picked up from my Italian grandmother—and love a good meal with my partner and her son, or gathering a group of friends.
What most interests you about the legal/technology/AI industry? What has surprised you the most about it?
What really excites me about legal tech is seeing how these tools cut down on the tedious, manual tasks and let legal professionals focus on the big picture. I’m also amazed by how quickly AI is evolving—it’s transforming legal research and making life a whole lot easier. The best part? Seeing firms eager to adopt these innovations.