Dru Armstrong was named CEO of AffiniPay, the parent company of LawPay, in July 2021. Less than a year later, AffiniPay shook up the legal tech landscape by acquiring MyCase, one of the leading law practice management platforms, in a deal that also included four other practice management products: CASEPeer for personal injury firms, Docketwise for immigration practices, Soluno for billing and accounting (which it recently sold), and Woodpecker for document automation.

One reason that deal was so notable was that, until then, LawPay had been the legal tech equivalent of Switzerland – a neutral integration partner with virtually every practice management platform out there. But in acquiring one of the major players in the market, that legal tech Switzerland seemed to suddenly lose its neutrality.

Now, two and a half years into the job as Affinipay CEO, Armstrong is our guest on this episode of LawNext to discuss that acquisition, where the company is today, and why the marriage of fintech and legal tech matters to legal practitioners. She also shares her plans for the company’s future, including how it will incorporate generative AI across its various products.

Armstrong and host Bob Ambrogi spoke live in Miami at the TLTF Summit, a conference produced by the Legal Tech Fund, a VC fund focused on legal tech, where she spoke on a panel on the intersection of fintech and legal tech. She was previously on this podcast in June 2022, at the time the MyCase acquisition was announced, and was also on our Legaltech Week podcast.

Thank You To Our Sponsors

This episode of LawNext is generously made possible by our sponsors. We appreciate their support and hope you will check them out.

  • Paradigm, home to the practice management platforms PracticePanther, Bill4Time, MerusCase and LollyLaw; the e-payments platform Headnote; and the legal accounting software TrustBooks.

  • DocReviewPad, the easy-to-use app to review, organize issue code, and produce documents

  • CARET serves over 10,000 firms with practice management and document automation technology to enable savvy professionals to refocus their expertise on what truly matters.

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Photo of Bob Ambrogi Bob Ambrogi

Bob is a lawyer, veteran legal journalist, and award-winning blogger and podcaster. In 2011, he was named to the inaugural Fastcase 50, honoring “the law’s smartest, most courageous innovators, techies, visionaries and leaders.” Earlier in his career, he was editor-in-chief of several legal publications, including The National Law Journal, and editorial director of ALM’s Litigation Services Division.