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The Kennedy-Mighell Report

Fresh Voices on Legal Tech with Jackie Schafer

·43 min·4 clips
A former wedding singer reveals how reading the room helps lawyers understand AI without technical jargon.
The episode begins with hosts Dennis Kennedy and Tom Mighell introducing their Fresh Voices series, aimed at showcasing diverse perspectives in legal tech. They welcome guest Jackie Schaefer, founder and CEO of ClearBrief AI, who starts by describing her background as a career litigator at firms like Paul Weiss and in government roles. Schaefer explains that ClearBrief is a Microsoft Word add-in that helps lawyers visualize evidence while writing, automate tedious tasks like site checking and hyperlinks, and is used by hundreds of legal organizations globally. When asked about communicating technology to lawyers, Schaefer attributes her skill to her past as a wedding singer, emphasizing the importance of understanding the audience's concerns, such as security and practical impact. The hosts then explore technology competence, with Schaefer noting that lawyers using ClearBrief tend to have a growth mindset, experimenting with AI tools in advance of deadlines. She details ClearBrief's features, including how it allows associates and partners to collaborate by sharing matter folders and automatically displaying evidence and legal sources. Schaefer recounts her career journey, highlighting a pivotal asylum case where visible evidence changed a judge's mind, inspiring ClearBrief's focus on evidence visibility. The discussion shifts to generative AI, with Schaefer advising against using ChatGPT for legal work and instead recommending purpose-built tools like ClearBrief, which offers features like instant hyperlinked timelines. She explains how judges and law clerks use ClearBrief to manage large records and improve efficiency. In the final segment, Schaefer gives best advice using a 'Back to the Future' analogy, urging lawyers to experiment with AI, and suggests ways for law students to enter legal tech, such as reaching out to founders on LinkedIn. She recommends following humorous legal tech voices like Conan Hines and Matt Margolis. The episode wraps with parting shots, including Schaefer's tip to use ClearBrief for automated table of authorities, Tom's recommendation of the Airolo app for travel eSIMs, and Dennis's use of ChatGPT as a project manager.

As heard by us

A grounded career story connects Paul Weiss, Alaska appellate work, and the legal experience behind Clear Brief.

This Fresh Voices episode looks at legal technology first as a career question, not a product pitch. The guest's path runs from a summer associate role at Paul Weiss in New York, where her first day coincided with Lehman Brothers' collapse, to in-house work at an Alaska native…

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Why you'd press play

You get a legal-tech career story that starts on the day Lehman Brothers collapsed and moves from Paul Weiss to Alaska appellate work.

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