‘I Couldn’t Get It Out of My Mind’: Chris Cartrett on Why He Is Leaving Aderant and Legal Tech

When I spoke with Chris Cartrett yesterday, just hours after reporting that he will step down Aug. 1 as president and CEO of Aderant, he was emphatic that his departure, after 12 years at the company, including five as CEO, was not about wanting to leave.

“It’s not a matter of wanting to leave Aderant,” he told me. “There just came a moment and an opportunity that, as it was presented to me, my wife and I both were like, this is interesting. … I couldn’t get it out of my mind.”

That opportunity, as I reported yesterday, is to become CEO of ImageTrend, a company that provides software and data analytics for emergency medical services, fire departments, hospitals and public safety agencies.

Cartrett is leaving legal tech at what he believes is a high point for Aderant, and he said the timing reflects the company’s strength, not any trouble beneath the surface.

“We have had so much great success here at Aderant with really great people, and I don’t see that changing anytime soon,” he said. “We’re hitting on all cylinders right now. It really was about a timing thing.”

Joining Cartrett on the call was Aisling Fenelon, who earlier this year became the company’s first female chief revenue officer, and who echoed that theme of continuity — although, she conceded, it will not be a change without emotion. “Chris and I are the crybabies of our exec team, for the record,” she joked.

Different Market, Familiar Mission

Emergency services software may seem a radical departure from legal billing and financial management, but Cartrett sees a through line between the two. ImageTrend, he said, is at a stage much like where Aderant stood several years ago at the outset of its own transformation, and the central challenge — connecting data to drive better outcomes — is the same.

“The reality is the connectivity of the data within that emergency services space [is what will] really help drive better outcomes for patients and for care,” he said. “It’s not unlike many of the things that are happening all across legal tech right now.”

What is different, he joked, is the jargon. “The acronyms are radically different. So I find myself now watching The Pitt and having to take notes on the side, so I can understand a lot of the vernacular that people are using.”

A Solid Management Structure

Asked about the management structure he leaves behind, Cartrett said that Aderant has been preparing for transitions like this one for years, pointing to a series of deliberate leadership moves.

Two years ago, then-chief operating officer Raphael Shure left to become president and CEO of PowerPlan, another company owned by Aderant’s parent, Roper Technologies. That move brought Aderant its current CFO, Kevin Janflone, in what Cartrett called “kind of a trade.”

Doug Matthews, whom Cartrett brought in as chief product officer in 2023, arrived with Lisa Erickson, who then took over as head of product and AI when Matthews left last year. “She has been phenomenal,” Cartrett said. “[She] completely drives all of our strategies [as they] relate to our platform, our AI strategy.”

Fenelon’s own promotion followed the same playbook, he said. When former CRO George Seymour left at the beginning of the year, “that had everything to do with the fact that Ash was ready.”

Between Fenelon, who has been at Aderant 11 years, and Chief Client Officer Josiah Chaves, who joined 12 years ago, Cartrett said the leadership team is deeply rooted. But his greatest pride, he said, runs deeper than the org chart.

“The thing that I’m the most proud of as I leave is that, if I look all the way through our business, the talent level inside of Aderant today is at a level that we’ve never had before.”

Fenelon said that Cartrett’s departure is significant.  “He’s such a big personality, he’s so important in legal tech.” But she said that his closeness to clients is an attribute the whole company shares.

“We are all deeply ingrained with our clients. That’s not just a Chris thing. That is an Aderant thing. That is an exec team thing. … Great companies are built on great teams, not on an individual.”

As for customers, she said they should expect no change of direction. “You’re going to miss Chris at Momentum, because, you know, the preacher likes to preach. But as far as our vision and our product roadmap and our customer commitments, none of that changes at all.”

Bringing Back Deane Price

To bridge the transition, Deane Price, Aderant’s CEO from 2017 to 2021, will return as interim CEO while Roper conducts a search for a permanent successor. Price will return July 20 to begin the transition and will serve as interim CEO when Cartrett formally steps down Aug. 1.

Cartrett said he was involved in that decision, and that Price, whom he called “truly my mentor,” was among the people he turned to as he weighed the ImageTrend offer.

He credited Roper for not rushing the succession. “Instead of trying to speed things up and try to ram a CEO in here, it was the other way around. It was like, hey, we’re going to take our time.”

Persuading Price took some doing, he said. “I did have to talk Deane off the lake. She was at her lake place, and it was like, you know, Deane, you come back — the people know you, they love you, they respect you.”

The search has been underway since early June, Cartrett said, and could conclude quickly or stretch to October or beyond.

The Final Grade on the Cloud

When I interviewed Cartrett at Aderant’s Momentum conference in 2025, I asked him what grade he would give himself on his signature mission of moving the company’s customers to the cloud. With his tenure ending, I asked for his final grade — and whether the customer reluctance I had sensed at that conference had persisted.

“I don’t feel that way anymore,” he said. “The majority of them are there.” On the core financial system, most customers have now moved, he said, while the rest of Aderant’s portfolio — “which has always been AI-enabled, cloud-based applications” — has grown “upwards of 300% over the last five years.” Just last month, he added, another Am Law 25 firm made the move to the cloud.

Fenelon said the momentum started in the mid-tier and has now reached the largest firms. Virtually every Am Law 100 firm she speaks with is either moving to the cloud or actively mapping out a transition over the next 12 to 15 months, she said.

She attributed the shift to the company’s approach. “There’s two ways to play this. We took the carrot approach, not the stick. … And so now you have these big, huge firms, like Holland & Knight and Baker Botts, that are in the cloud and munching on that carrot and seeing improved performance and taking advantage of AI in a way they never could on prem.”

On AI adoption more broadly, Cartrett said the hesitancy of two years ago is gone. He pointed to the recent release integrating Aderant’s iTimekeep with Harvey.

“Firms are so far down that road with Harvey, [Legora], all these other players, [that] bringing that type of efficiency into your back office, with what we’re doing with MADDI and then across other tools, I feel like, is literally a no-brainer now.”

Any regrets? “There is never a day I wake up that I don’t kick myself thinking I did something too slow,” he said. The company began building out its platform roughly three years ago, and it is now delivering “real return for our clients today. … I wish I had known to do that five years ago.”

The Billable Hour Will Remain

As for reports of the death of the billable hour, Cartrett does not foresee it disappearing. But he believes it will occupy a smaller share of the pricing mix as clients demand that firms translate AI-driven efficiencies into lower or more predictable costs.

“The billable hour will remain,” he said, “but I will be crystal clear: Law firms, ultimately, over the course of the next four years, are going to have to shift more and more to outcome-based billing. Every client is asking for efficiencies as it relates to AI and its impact on the bill.”

Fenelon was more sanguine, noting that the profession was predicting the death of the billable hour 25 years ago.

“It doesn’t matter, as long as we’re prepared for the inevitability, whatever that happens to be,” she said. “As long as we have a technology that can support that outcome, or the hybrid of that outcome, then we’ve done our job.”

For Cartrett, the deeper issue is how firms articulate their value. “Most law firms pitch their value based on hours. And what I was trying to explain was, no, your value is your brain — the way you come at this information, the creativity. That’s your value.”

Advice for His Successor

Does Cartrett think Aderant’s next CEO needs legal industry experience? “I do not. I can tell you that up front,” he said.

What the next CEO will need is the ability to lead Aderant through a shift he believes is coming for all of software.

“This idea of applications and products — that world’s gone. It is truly about an operating system and how you’re able to enable things. And that’s going to require an entirely different approach to how you serve your clients.”

His advice for whoever gets the job: Lean on the team. “Our team is so open and free in conversation. We never have a meeting where there’s something left unsaid. No, it’s said, and then we want to go attack it.”

Also, he added, understand the community. Over the last week and a half, as he began telling customers of his departure, “they have been so genuinely happy for me. … I’ve received a zillion emails today, just encouraging emails for me as I go on this next journey.”

The Aderant community of employees and customers, he said, “is unlike anything I have ever dealt with in my life,” and leaving it is what makes him most nervous.

A Parting Warning for Legal Tech

Asked for his unvarnished take on the industry he is leaving after nearly three decades, including his years at Thomson Reuters before Aderant, Cartrett said legal has flipped from laggard to leader.

“We’ve gone from always being laggards to, all of a sudden now, legal is moving forward faster than most industries out there.”

But his optimism about legal’s accelerating adoption of technology came with a warning: The gap may widen between companies that have modernized their architecture and those still maintaining aging systems.

“There are a lot of legal tech companies that have been owned by people for a long time, and they’ve kind of dealt with a little bit of the tech debt, but they’ve not really addressed the problems in the world that we’re all moving into.

“Data is just so critically important. Security becomes more important than ever. And so, if you’re just playing around, limping along [with] some of these old legacy systems, you better be careful.”

Law firms, he said, get this. “They understand that … it’s a new world out there.”

As for Aderant, Cartrett’s assessment was simple: “It’s a unique place. It’s a unique business. It’s one I’m very proud to have been a part of.”