Ari Kaplan, a legal industry analyst and the host of the Reinventing Professionals podcast, recently spoke with the following leaders at the 2026 International Legal Technology Association Annual Conference for his annual mixtape.

Ari Kaplan: What are you looking forward to at ILTACON 2026?

Ross Guberman, founder and CEO, BriefCatch: We’re exhibiting, but I’m really looking forward to wandering around and seeing what’s coming. It’s hard to know where the whole legal tech industry is headed, but I would like to figure it out this week. I noticed yesterday that there are a lot of new players in the exhibit hall, and I’m eager to see what they’re up to and whether it signals any shift in where products are headed. We’ve been a deterministic product for the most part until a few years ago, when we moved into generative AI. What’s exciting now is finding the sweet spot between the two and figuring out the right workflow and architecture to benefit from the advantages of code and AI.

Ari Kaplan: How has AI transformed your business and the business of your clients?

Anthony Seale, founder and CEO, Legatics: We’ve been trying to adopt AI internally. I met some people who were experimenting with MCPs very early, and I actually went on a weekend retreat to Scotland with them. We had to use a code development environment, an IDE, to try this way of working. It was the first time I’d used AI to connect to all of my different tools. I connected it to my calendar, Salesforce and the tools we use internally to run a legal technology company. Soon, that became a model for how lawyers could work. So now we’re bringing Legatics, as a central source of truth for transactions via an MCP, into our clients’ world. It brings a very fluid, cross-platform way of working, with AI at the center. Working in this way has completely transformed how I work and my life. But I don’t think lawyers are quite there yet. They’re on the cusp, and I’m excited to bring that to the world.

Ari Kaplan. (Photo by Tori Soper)

Ari Kaplan: What are your expectations for this year’s ILTA conference?

Beau Wysong, chief marketing officer, Opus 2: ILTACON has been different this year. It feels like it’s grown to a scale much bigger than in years past. There’s a wider variety of attendees across the ecosystem, and the exhibit hall has really taken off. So it’s about staying relevant in the industry and making sure our message as a business partner can be heard, even with all the noise. The biggest driver of change, obviously, has been technology. Two years ago, AI was a cool idea, and that quickly became a reality last year. It’s exploded this year through use cases, and it’s grown larger in two years than anyone could have imagined. It’s become real. As a result, everyone’s trying to keep up and make sure we’re using it as effectively as possible. We launched Opus 2 Ingenuity, our agentic AI framework. It’s the culmination of a lot of work to galvanize all the AI we’ve had out in the market before, and we’re excited to share it.

Ari Kaplan: What questions are you hoping to answer for clients and prospects at this year’s event?

Beth Thompson, vice president of market strategy and legal evangelism, Actionstep: AI is top of mind for everyone right now, just at different levels of curiosity. I’m interested in understanding where people are in that journey. Have they taken the plunge? Are they considering it in the next 12 months? What are they worried about? ILTACON is the perfect forum to guide them through options and show them how to run their firms more efficiently. I’ve been coming to the conference for years, and it’s still the best week of the year. The energy is incredible, and you’re surrounded by smart people you learn from constantly. It’s the one time of year we can set competition aside and just work together to push the legal tech industry forward.

Ari Kaplan: What are you trying to convey at this year’s ILTA conference?

Dan Malgran, vice president of marketing, Steno: When we look at how we market to lawyers, to knowledge management and to law firms in general, we think about the humans first. Many companies market B2B and think of it as the firm buying this or the firm’s personality buying this. We see it more as the individual making the decision, and people like to connect with others. They like to be wowed, amazed by different things. So when we heard that the theme overall for ILTACON this year was musicals, we went back and forth. We have a very creative team. We have a field team. We have a brand team. We went back and forth on a couple of different ideas and eventually settled on Legally Blonde. That morphed into the “What? Like, it’s hard?” So all across our social, we’re running, “What, like, litigation support is hard?” “What, like, depositions are hard?” And we’re also feeding into the education around why we know that space and how we make that easier for people to make their jobs easier and to understand their workflows. We’ve even found that just by going in on the theme, so many people are coming up to the booth, and they’re wowed. It has a different look and feel from everything else on the floor.

Ari Kaplan: What do you think of your first ILTA conference?

Eileen Penta, senior account executive, Clarra: It’s truly amazing to be in a room with so many educated people at a time of rapid change in legal technology. I’ve caught up with so many friends and made new ones. Everyone is here and receptive to conversation, and everyone’s learning in real time. With this technology boom, every firm is using a decision tree to choose which technology to adopt, how to approach it, and how to learn information governance to make their litigation process easier. Everyone is opening their eyes to what’s available right now, and it’s an incredible time to be part of it. I have a background as a trial paralegal in New York City, and seeing the tools you have now versus then is mind-blowing.

Ari Kaplan: What do you think of this year’s ILTA conference?

Faith Benson, vice president of marketing, SimplyAgree: It feels like legal tech has really arrived. I come from a traditional SaaS background, and when I started in legal tech, everything felt like we were catching up to what was happening in the valley. Now, it feels like the valley has arrived in legal tech. It’s exciting to hear from customers how they’re each approaching this new world and to think about how the ecosystem connects. That’s been a really positive development over the last year with the adoption of horizontal AI. It’s put everybody in an ecosystem mindset, rather than a shelf of separate tools they tap into for different things. SimplyAgree’s based here in Nashville, so my team gets to choose some really awesome local spots to bring our customers and friends.

Ari Kaplan: What are your expectations for this year’s ILTA conference?

Gabriel Karawani, co-founder, ClearPeople: My expectations are to meet lots of prospects, customers and partners and to have conversations about the craziness that is legal tech today. Just on the plane on the way over here, we had half a plane full of U.K. legal tech leaders, and conversations were going on throughout. We all feel there’s a massive opportunity to solve problems that have been in front of us for the last 10, 20, 30 years. A lot of people feel that this is the time to solve them, but at the same time, we’re still carrying some of the old burdens, some of the old legacies, and some of the traditional system problems. Before we do, we can’t leapfrog ahead with the latest technology.

Ari Kaplan: What questions are you receiving at your booth this year?

Ginger Shimp, vice president of marketing, Fulcrum Global Technologies: Of course, everybody’s talking about AI, and it’s probably the hardest question to answer because everybody also has an answer. But our focus is that AI will amplify what you do badly as much as it will amplify what you do well. So the human in the loop is central to what our company is built on. Our CEO, Ahmed Shaaban, said you can either manage AI strategically or reactively, and we are here to help our customers manage it strategically.

Ari Kaplan: What was your vision for this year’s ILTA conference, and has it come to fruition?

Joy Heath Rush, CEO, International Legal Technology Association: Well, I’ll tell you, Ari, everything is changing so rapidly. Any vision more than four weeks in advance is probably already outdated. Based on our early registrations and sponsorships, we saw the community excited to be together in this time of incredible change. Two years ago, the conversations were, “Should we?” Last year, the conversations were, “Here’s how.” Now, the conversations are, “What’s next?” And in terms of the focus, our friend Jim McKenna says, “What’s next after what’s next?” That is what I was hoping for, and I think we have definitely seen it.

Listen to the complete interview at Reinventing Professionals.

Ari Kaplan regularly interviews leaders in the legal industry and in the broader professional services community to share perspective, highlight transformative change and introduce new technology at his blog and on Apple Podcasts.