From legal pads to AI-enabled in one year

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Jen Barry

Hopkinson & Abbondanza

  • 1990

    Year Founded
  • 25-30

    Number of Staff
  • 2024

    Started Using Clio
  • Portland, Maine, USA

    Location
  • Flat Fee

    Hourly

    Fee Types
  • Corporate Governance and Business Planning

    Estate Planning

    Real Estate

    Practice Areas

Jen Barry, Managing Paralegal, Estate and Trust Administration

Hopkinson & Abbondaza had been practicing law for 36 years without case management software. No central system. No shared record of a matter. No single place where the work of five attorneys, four paralegals, and a dozen-plus support staff across two Maine offices came together. They had legacy billing software, but it didn’t connect to modern tools, and was unable to serve as the kind of connected platform they felt their growing, multi-practice firm needed.

The firm built a strong, well-regarded practice across estate planning, real estate, corporate law, and civil litigation, delivering excellent results for clients over more than three decades. Still, behind the scenes, the administrative work was heavy. Knowledge lived with individuals rather than in shared systems, and keeping things organized across practice areas became more difficult as the firm continued to grow.

When Jen Barry joined the firm in May 2024 as senior paralegal and department head for trusts and estates, the partners recognized her background in legal technology, and saw an opportunity.

“Hey, by the way, we’ve needed case management for, I don’t know, 35 years, could you help?”

In 25 years of estate planning work, this was the third firm she’d joined that had no case management at all. But the willingness to ask the question, and to commit to real change, set Hopkinson & Abbondaza apart from the start.

Going all-in

Jen had deep experience with other platforms from prior firms and knew what to look for: not just features, but how a system would hold up across multiple practice areas and a staff with varying needs. So, she started demoing products. A couple of former colleagues highly recommended Clio, and after evaluating several options, she presented her recommendation. The partners didn’t deliberate long. “They basically just handed the project to me and said, take it and run.”
The firm signed with Clio in late 2024 and attended ClioCon that fall before starting to work in the software. At ClioCon 2025, Jen watched from the floor as two of the firm’s partners sat up in the balcony during the keynote. Their phones came out at first, but then the phones went away. The announcement of Clio Work had their attention and the partners were leaning forward, completely riveted by the presentation. They came back down electric.

“Did you see what that thing can do? We need to talk about this.”

During the keynote, it became clear that Clio was more than a case management system—it was a connected platform that could transform the firm’s operations. With AI-powered research, document drafting, and automated calendar management all tied to the same matters and the same data, disconnection and administrative burden would fall away, and the firm could make an impact with its work like never before. The firm committed to fully implementing a robust platform, including AI tools, and document automation for the entire team, with onboarding for the new tools starting at the end of 2025.

What the work looks like now

A year in, their vision was realized. The same firm that was running on individual memory and manual processes now has an AI-assisted platform humming across every department.

A junior partner—a litigator working without a dedicated paralegal—started using Clio’s AI tools to draft memos, produce stipulated orders, and build frameworks for court filings. Instead of starting from a blank page every time, he always had a usable, structurally sound starting point ready for review. Jen saw similar results when she was asked to draft a stipulated order outside her specialty. She described the matter in plain terms, and what came back needed almost no revision.

“The quality of the product that came out was amazing. It needed a little bit of revision and it was not even really content revision. It was just preference.”

Asked how much time and effort the AI tools are now saving her, Jen didn’t hesitate. “Oh, I’d say hours.” For work outside her core specialty in trusts and estates, where the formatting and framing are unfamiliar, the time savings were, as she put it, “immeasurable.”

On the administrative side, junior staff started feeding scheduling orders into the system to populate attorney calendars with calculated deadlines. Work that previously required step-by-step retraining every time it came up now simply happened in seconds. “This just removes that element,” Jen said. “This removes the need for us to physically enter that information.”

The firm’s research process shifted, too. Before Clio, the attorneys relied on free tools and, in some cases, physical books. With Clio, they got reliable legal research inside the same environment where their matters lived, and the confidence that a closed system kept client information protected.

“It was very important to me to know that Clio uses a closed-loop system and that our client information was not going to be exposed in any way.”

An unstoppable team

What makes this story remarkable isn’t just the technology. It’s how quickly the entire team embraced it. In just one year, Hopkinson & Abandanza implemented a single, shared home for their legal work and the work of running the firm. Matters, research, documents, deadlines, communication, all in one system, accessible to everyone.

Jen did great work to help the transition work for everyone, building on an incredible culture built by the partners that helped foster such rapid transformation.

At a recent partners meeting, Jen expected to deliver a routine technology check-in. Instead, the managing partner started sharing his screen to walk the room through what he’d been doing in the platform. Then a senior partner, someone who still brings a yellow notepad to every client meeting, and who had been candid about his skepticism toward new technology, asked Jen to show him how it worked. He saw what the rest of the team was doing and wanted in.

“To have him show excitement in this meeting, and to have him be interested in the use case that he might have for it, and to actually ask for training. That is not anything like what I was expecting to have happen.”
From the youngest associate to the most experienced partner, the whole team adopted the platform and continues to adapt and find new opportunities. Today, everyone at the firm is looking forward to the lasting impact of this digital transformation, both for their firm, and for the clients they serve