Robert "Bob" Ambrogi is a Massachusetts lawyer and legal journalist who has been writing and speaking about legal technology, legal practice, and legal ethics for more than two decades. He authors the award-winning blog LawSites (since 2002), writes a longtime column for Above the Law, and hosts LawNext, a leading podcast featuring the innovators driving what's next in law.
Maui Gevero is a legal pricing and analytics leader who partners with corporate legal departments to modernize outside counsel engagement and drive measurable value. As Senior Manager of Legal Advisory at PERSUIT, he advises global in-house teams on data-driven sourcing strategies, alternative fee arrangements, and market-based pricing solutions.
Stop building separate AI playbooks. Learn how one legal department and firm collaborated successfully—and gain a step-by-step framework, pricing tactics, and proven results to replicate today.
What Will You Learn
Attorneys will learn how a corporate legal department and law firm developed one shared AI playbook together instead of building separate playbooks.
What Will You Gain
Attorneys will gain a step-by-step overview of what was built, the collaboration's origin story, and the short- and long-term business impacts of the relationship.
Key topics to be discussed:
This course is co-sponsored with myLawCLE.
Date / Time: May 21, 2026
Closed-captioning available
Moderator, Bob Ambrogi | Above the Law
Robert “Bob” Ambrogi is a Massachusetts lawyer and legal journalist who has been writing and speaking about legal technology, legal practice, and legal ethics for more than two decades. He authors the award-winning blog LawSites (since 2002), writes a longtime column for Above the Law, and hosts LawNext, a leading podcast featuring the innovators driving what’s next in law. He also hosts Legaltech Week, a weekly legal tech journalists’ roundtable. In addition to his journalism, Bob represents news organizations and serves as executive director of the Massachusetts Newspaper Publishers Association, which advocates for the First Amendment and freedom of the press.
Bob is a 1980 graduate of Boston College Law School and is admitted to practice in Massachusetts. He has built his career at the intersection of law, journalism, and technology, becoming one of the most widely recognized voices covering legal innovation in the United States.
Bob was named to the inaugural Fastcase 50 in 2011, an honor recognizing “the law’s smartest, most courageous innovators, techies, visionaries and leaders.” In 2017, he received the Yankee Quill award for journalism from the Academy of New England Journalists and was honored by the ABA Journal as a Legal Rebels Trailblazer. His earlier honors include the 1993 President’s Award from the Massachusetts Bar Association. His LawSites blog has been repeatedly recognized among the top legal technology blogs, including induction into the ABA Journal’s inaugural Blawg 100 Hall of Fame in 2012.
Bob is a fellow of the College of Law Practice Management and a past-president of the Massachusetts Bar Foundation. For 13 years, he co-hosted Lawyer2Lawyer, the longest continuously running legal podcast, produced by the Legal Talk Network, before signing off in 2018. He also wrote the Web Watch column for Law Technology News (now Legaltech News) from 1999 to 2013.
Bob has spent more than four decades at the forefront of legal media and legal technology coverage. Earlier in his career, he served as editor-in-chief of The National Law Journal and as editorial director of ALM’s Litigation Services Division. Before joining ALM, he was with Boston-based Lawyers Weekly Publications, where he was the founding editor of Lawyers USA and editor-in-chief of Massachusetts Lawyers Weekly. In 1994, he founded legal.online, the first internet newsletter for lawyers. Today, through LawSites, LawNext, Above the Law, and Legaltech Week, Bob continues to chronicle the people, products, and trends reshaping the practice of law.
Maui Gevero, Legal Advisory | PERSUIT
Maui Gevero is a legal pricing and analytics leader who partners with corporate legal departments to modernize outside counsel engagement and drive measurable value. As Senior Manager of Legal Advisory at PERSUIT, he advises global in-house teams on data-driven sourcing strategies, alternative fee arrangements, and market-based pricing solutions.
Professional foundation rooted in finance, legal pricing, and compliance with a blend of financial services expertise and sophisticated law firm pricing strategy.
Serves in a senior leadership role within the Legal Advisory team at PERSUIT. Selected as a featured speaker at industry events including General Counsel Conference East, sharing insights on legal pricing trends, alternative fee structures, and the impact of AI and analytics on legal services delivery.
Active participant in the legal operations community contributing to ongoing dialogue around innovation in legal procurement and value-based pricing. Engages with corporate legal leaders, law firms, and industry organizations to advance transparency, efficiency, and strategic alignment in the legal marketplace.
Prior to joining PERSUIT, served as Senior Financial Analyst on the pricing team at Latham & Watkins, leading complex client pricing engagements and developing financial models supporting high-value matters and alternative fee portfolios. Earlier held roles at Goldman Sachs in compliance and asset management, developing analytical foundation and experience navigating regulatory frameworks and sophisticated financial environments.
SESSION 1 – The Collaboration Gap is the Real Problem | 1:00pm – 1:20pm
Despite parallel AI investments, only 3% of corporate legal departments and law firms pursue a joint adoption strategy. This siloed approach mirrors the billable hour’s fragmented evolution and prevents both sides from capturing AI’s full strategic value
SESSION 2 – Start Small, Measure Everything, Build from There | 1:20pm – 1:40pm
Successful AI collaborations begin with focused pilot projects rather than sweeping overhauls. Teams should define clear metrics from day one, track outcomes rigorously, and use early wins as the foundation for scaling adoption across broader workstreams
SESSION 3 – Pricing Must be Part of the Collaboration from Day One | 1:40pm – 2:00pm
Pricing cannot be an afterthought in AI partnerships. Embedding fee discussions into the collaboration’s foundation ensures efficiency gains translate into transparent, value-based billing that aligns law firm incentives with corporate client expectations and shared business outcomes.