At Aderant’s Momentum Global Conference, A Drive Towards AI-Enabled Cloud Innovation and ‘Unmatched Client Experience’

As he took the stage before the nearly 1,000 people assembled in the ballroom of the Omni Hotel in Dallas to open his company’s Momentum Global 2025 user conference May 20, Aderant President and CEO Chris Cartrett said he preferred to think of his talk not as a keynote, but as a kick-off. But by […]

As he took the stage before the nearly 1,000 people assembled in the ballroom of the Omni Hotel in Dallas to open his company’s Momentum Global 2025 user conference May 20, Aderant President and CEO Chris Cartrett said he preferred to think of his talk not as a keynote, but as a kick-off. But by the time I left the conference two days later, I could not help but think that his kick-off – and much else at the conference – was also a bit of a kick in the butt.

Even as Cartrett (pictured above) and other speakers heralded the benefits of the company’s new generation of AI-enabled, cloud-based business and financial management products, they did so to an audience that is still betwixt and between – with many users still loyally rooted in the terra firma of the on-premises products upon which Aderant originally built its reputation.

Ever since 2017, when Aderant first released Expert Sierra, the cloud version of Aderant’s Expert financial management software, the company’s sights have been set squarely on the cloud. When Cartrett – with Aderant since 2014, after moving there from Thomson Reuters – was named CEO in 2022, his express mission was to aggressively advance a cloud-first strategy throughout Aderant’s suite of solutions.

The company significantly advanced that strategy at last year’s Momentum conference with its release of Stridyn, an AI-driven cloud platform designed to unify all of Aderant’s cloud products within a cohesive interface.

And it further advanced that strategy at the conference with the launch of another four cloud-based applications – Cloud Accounts Receivable (AR), Cloud General Ledger (GL), Stridyn Analytics, and askMADDI – and enhancements to other cloud applications, such as AI-powered generation of billing narratives in iTimekeep.

The momentum on display at Momentum has proven successful for the company. In his kick-off, Cartrett highlighted 2024 as a record-breaking year for the company’s growth and said 2025 was on track to be even stronger.

Driving much of that growth was Sierra, the cloud version of Expert, which grew by 234% over the last two years, Cartrett said. In just the first quarter of this year, 11 new firms have gone live on Sierra, and last year, 47 firms went live. To help drive all this, the company hired 110 new employees in 2024.

But it cannot be overlooked that Aderant, after all, is a company whose roots go back nearly 50 years to its founding in 1978. For many of those earlier years, it was on the strength of its on-premises products that it was able to establish and build a significant customer base among large and mid-sized law firms.

Even in the face of all this momentum towards the cloud and AI on display at the conference, I spoke to several customers – primarily at larger law firms – who told me they are quite happy with their on-premises versions of Aderant’s software. They said they have no interest in moving to the cloud – at least not for now.

Some told me that they spent years customizing and tailoring the software to make it a perfect fit for their firm, and, having done that, they are in no hurry to walk away.

So when I say that Cartrett’s kick-off might also have been a bit of a kick in the butt, I do not mean to suggest that he is pushing any of his customers off on-premises versions of Aderant’s software.

In fact, I directly asked him whether Aderant had any plans to follow the example of e-discovery company Relativity – another business that built its reputation on its on-prem software long before building its cloud platform, and which recently announced that it will require all new cases to be in the cloud starting in 2028.

Cartrett responded that he has no plans to do anything similar, and that if such a date were ever to come, it would be very far off into the future.

Still, to this observer, it did feel that Aderant is performing a delicate balancing act between its legacy customers and its cloud customers. And, to the extent it is a balancing act, then for any customers still teetering, Aderant is explicitly, if gently, encouraging them to join the cloud side.

In fact, during the opening session, Andy Hoyt, Aderant’s chief technology officer, and Josiah Chaves, an Aderant veteran who was recently named the company’s chief client officer, made this crystal clear through two slides they presented.

The first, titled “The Path of Innovation Adoption,” outlined how transitioning to the cloud would “revolutionize your experience and productivity” and enable customers to “fully leverage the cloud’s potential and our refined, feature-rich platform.”

Following that was a slide titled, “Come to Sierra” that outlined the key benefits for customers of moving to Aderant’s cloud platform:

• Stridyn Analytics.
• Next-gen financial management.
• Stridyn architecture and platform services.
• Powerful integrations.
• MADDI automation and insights.
• Robust cloud infrastructure.
• Enhanced UI.

Clearly, Aderant’s leadership sees the future in the cloud. And many of its legacy customers have already made that move and all its new customers start there.

But for those customers still using Aderant’s on-premises software, maybe Momentum’s three days of product releases and in-depth demonstrations will motivate them, at last, to let go their earthly tethers.

New Cloud Financial Apps

As Aderant’s executives took the stage last week to announce these new products, the centerpiece was Aderant’s launch of four cloud financial management applications. Together, the applications represent a major step forward in the company’s transition to the cloud, as well as in its plans to integrate AI across every product and every workflow.

At that product announcement session, Derek Schutz, director of product management, platform and data, demonstrated how the new Cloud Accounts Receivable module can automatically process cash receipts, match invoices, and handle complex allocation scenarios with minimal human intervention.

“Very easy, very all in one place, very simple to navigate around,” Schutz told the audience.

The Cloud General Ledger application, meanwhile, is aimed at automating what has historically been one of the most manual aspects of law firm financial management. As Michael McKay, vice president of engineering, explained during a demonstration, the new system allows drill-down inquiries that allow users to trace any journal entry all the way down to its source – whether it is a time entry, AP invoice, or bill – without having to involve IT staff or run custom SQL queries.

“It’s really able to give you that 360-degree view of your data so you can see everything that’s going on without having to involve other people in that process,” McKay said. 

MADDI AI Integration

Another development highlighted at the conference was Aderant’s extension of askMADDI, Aderant’s AI assistant, across all its cloud applications. Aderant first released MADDI two years ago, and last year made askMADDI available on a limited basis within specific products. But now it is integrated within the Stridyn platform and able to deliver context-aware answers in any of Aderant’s cloud applications.

CTO Hoyt described askMADDI as a “virtual associate” that can field natural language queries about firm data and operations. During a demonstration, he showed how a user can ask a question such as, “Give me the top client by AR balance,” and quickly receive a formatted response that could be exported or further refined.

Hoyt emphasized that the AI isn’t just about data queries but also about system guidance. “AskMADDI will tell you exactly step-by-step how to do that,” he said, referring to the system’s ability to provide procedural guidance for complex software tasks.

Hoyt and Chief Product Officer Doug Matthews outlined what they described as Aderant’s four strategic pillars for AI development:

• Customer centricity, meaning the development starts with customer need and value.
• Responsible AI, meaning it is developed responsibly in a human-centric way.
• Domain excellence, meaning it is developed with “unmatched” knowledge of the legal tech domain.
• Technical excellence, meaning it is building products using state-of-the-art AI architecture.

One-Touch Time Entry

While the bulk of Momentum’s attendees are law firm finance and billing professionals, it is the legal professionals who may be particularly interested in one of the new uses of AI in a product unveiled last week.

That product is the new version of iTimekeep Premium, which extends the passive-timekeeping capabilities that were already part of the product to enable what Cartrett described as “one-touch time entry.”

Now, iTimekeep uses AI to automatically plug-in action codes and work descriptions based on matter details and document analysis, significantly reducing the manual work required for time entries.

Unlike some other passive-timekeeping products on the market, Cartrett said, iTimekeep’s AI is trained on real results drawn from Aderant customers, learning from the vast amounts of clients’ historical data drawn from Aderant’s BillBlast product to understand when time entries are accepted or not.

“We know information about our clients and what actually gets paid,” Cartrett told me. “We know what gets rejected, we know what is accepted.”

‘Borderless’ Service Strategy

Beyond products, a central theme throughout the Momentum conference was delivering an “unmatched client experience,” as Cartrett described it. This is a primary strategic focus for the company, he said, with multiple executives and initiatives aligned around transforming how Aderant serves its law firm clients.

In his opening kick-off, he used an analogy to a restaurant he frequents to illustrate the transformation Aderant seeks to achieve.

“The word we would use, unmatched. It was an unmatched experience inside that restaurant. So that, to me is what I want to talk about for all of you. I think where we need to be as a business and what my promise is to all of you is that Aderant is going to give you an unmatched client experience.”

He described a three-pillar approach to achieving that:

1. Product Innovation: Encompassing enhanced software capabilities and AI integration.
2. Process Improvement: Including streamlined internal operations and self-service capabilities.
3. People and Structure: Organizational changes within Aderant to eliminate silos.

Cartrett highlighted the recent appointment of Josiah Chaves as chief client officer, emphasizing a new “borderless” approach to client service that is intended to eliminate handoffs between departments.

Chaves, speaking at the event, outlined his role as bringing together traditionally siloed functions.

“It really is about bringing this roadmap to life through our service delivery,” Chaves said. “And as we think about how to connect with you better and more strategically, it is about all of us across Aderant understanding the things you’re trying to accomplish as a firm.”

In this new role, Chaves said, a major focus of this will be on enhancing customers’ experience in migrating to Sierra and reducing their effort in making that migration. Key aspects of this include:

• Verification-ready onboarding, in which Aderant’s services team now handles some 650 critical tests for Sierra migrations.
• A new “hypercare” program providing extended post-implementation support at no additional cost.
• Business-critical account management, providing a higher level of white-glove service for select clients.

Even before launching these programs, Chaves said, Aderant’s service improvements had resulted in 20% faster time to resolve support tickets and 25% reduction in support tickets.

“But we think we can do better,” he said, “and so we’re continuing to build out new programs to connect to you in a way that helps you accomplish that migration into Sierra.”

Related to this is a new initiative to provide customers with an expanded array of self-service capabilities. These include:

• Redesigned and expanded Aderant Academy, the company’s product-learning portal, with learning plans and snippet videos.
• An elevated customer enhancement portal, where customers can submit product requests and other customers can vote them up or down. So far, customers have submitted 529 ideas, of which nine have shipped and 59 are currently in development.
• New knowledge base articles, designed to address gaps in documentation.
• Self-serve dashboards for all Aderant apps, all of which will also include mobile access.

In his opening remarks, Cartrett described this new approach to customer service as “establishing a borderless experience across our solutions and assisting our clients in solving their biggest business challenges.”

Executives in the Hot Seat

Another core theme of the conference was transparency, and that was best demonstrated in 90-minute “Hot Seat” session during which a series of executives took the hot seat to face pointed questions about the company’s recent challenges.

Aisling Fenelon, Aderant’s vice president of North America sales, was candid when asked about the company’s historical weaknesses in reporting.

“Where I feel like we’ve fallen short … is in that management layer in between,” she said. “How do you actually look at all the ships in the sea and understand where they’re going and where you might want to turn in a different direction?”

But pointing to the launch of Stridyn Analytics at the conference, she added, “But I do think that we are turning it around pretty quickly.”

When he took the hot seat, CTO Hoyt provided insights into Aderant’s technical evolution and quality initiatives. He revealed significant improvements in system reliability, having reduced system regressions by 70%.

But he said even that was not enough, and the Cartrett had given him and his team their marching orders: “Within the next year, no regressions in software.”

For his part, Cartrett, asked about his biggest mistake as CEO, said it was in not pushing himself and the company hard enough in his early days of taking the helm.

“I look at when I first took over, I think there for a little while we had settled on what we were doing was winning, but we weren’t pushing ourselves to not just lead, but dominate – dominate in a way that we don’t let the little startups be the creative idea leaders.

“Why aren’t we doing the creative ideas? I feel like too often we were first to be second and I don’t necessarily know that was the right strategy as we transition more into being the more creative leader.”

The Road Ahead

I had a chance to sit down with Cartrett at the conference and record an interview for my LawNext podcast, which should be released sometime soon. In that interview, he painted a picture of an industry – and a company – in transition.

“Right now, I’ve got seven different product lines serving seven different groups o,” he said. “You can already see the handwriting on all of this – which is merge to where it becomes something that is more of a monumental change,” suggesting a future where individual applications give way to integrated workflows.

A big piece of driving that integration will be AI, he said. Too many law firm executives fear that AI will replace jobs, he suggested, whereas the reality is that it will help them do their jobs better.

Building A Community

For someone like me who writes about legal tech, attending a user conference can be enlightening. Too often, much of what I hear about a company is spoon fed to me by its executives and marketing teams. But at a user conference, I get unfettered access to the actual users, as well as to some of the more rank-and-file people who work at the company.

My takeaway was that there is unique culture within Aderant’s user community. In his opening remarks, Cartrett asserted, “I would argue there’s about 600 people in this room that have my cell phone number.” I have no way of verifying that claim, but I did hear from customers that they appreciate the approachability and transparency of the company’s leadership.

This seemed evident throughout the conference, from the Hot Seat session I described above where executives fielded tough questions to the pavilion area where clients demonstrated their own innovations using Aderant technology.

At one point during the Hot Seat session, in what appeared to be an unscripted exchange, the moderators invited Frank Puleo, president of the independent, nonprofit Aderant Expert Users Community, to stand up in the audience and offer his thoughts on the conference and what could be done to improve it in future years.

Puleo, associate director of finance systems at Proskauer Rose LLP, offered several suggestions for improving the conference, such as more diverse training content – including more in-depth content for customers who are still on Expert – and better categorization of sessions by intended user.

From what I could tell, the conference drew attendees from law firms globally, ranging from major international firms to smaller regional firms. Of the attendees I spoke to, some were new to Aderant, some were old-timers.

But the common thread throughout was that they are all grappling with similar challenges around efficiency, compliance and client service in an increasingly competitive legal market.

In the face of those challenges, the conference made clear that Aderant is positioning itself as not just a software vendor to law firms, but as a strategic partner.

The success of that strategy will likely be measured not just in product adoption, but by whether Aderant can deliver on Cartrett’s promise of an “unmatched client experience.”