legal-operations
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Evan Wong
Evan Wong is the co-founder and CEO of Checkbox, a legal AI company he started in Sydney in 2016 and now runs from New York. Checkbox builds an AI 'legal front door' that lets in-house legal teams intake, triage and automate routine work through a no-code, drag-and-drop platform. A serial entrepreneur who launched his first company at 17, Wong studied Commerce and Law at UNSW, was named to Forbes 30 Under 30 Asia in 2019, and in early 2026 raised a US$23M Series A that valued Checkbox at roughly US$100M. His customers include large enterprises such as PepsiCo, SAP, Telstra and Woolworths.
Jim Delkousis
Jim Delkousis is the founder and CEO of PERSUIT, a New York-based legal technology company that helps corporate legal teams run competitive, transparent processes for hiring outside counsel. A former DLA Piper litigation partner with 25 years in BigLaw, he left the partnership in 2016 to build a platform that shifts legal buying from billable hours toward outcomes and value. PERSUIT now works with Fortune 1000 legal departments and thousands of law firms, and in 2025 expanded into legal spend and matter management by acquiring Apperio.
Olga V. Mack
Olga V. Mack is the CEO of TermScout, an AI-powered contract certification platform that grades contracts as fair, balanced, and market-ready before negotiation even begins. A serial legal-tech CEO and former general counsel, she earlier ran Parley Pro through its 2022 acquisition by LexisNexis and stayed on to lead CounselLink. She is a six-time TEDx speaker, a Stanford CodeX fellow, the Generative AI Editor of the MIT Computational Law Report, an adjunct professor at UC Law SF, and the author of multiple books on boards, blockchain, and legal operations. Born in Ukraine and educated at UC Berkeley, she has spent her career trying to make law less of a bottleneck and more of a service.
Kathy Zhu
Kathy Zhu is the co-founder, CEO, and general counsel of Streamline AI, an intelligent intake and workflow automation platform built for in-house legal teams. A former first commercial lawyer at both Medallia and DoorDash, she built Streamline AI to solve the bottleneck she lived through firsthand - legal teams drowning in unstructured requests with no metrics to prove their value. Born in Shanghai and raised across four continents, she trained as a corporate lawyer at Wilson Sonsini before deciding that the tool she wished existed was worth leaving a dream job to build.
Basha Rubin
Basha Rubin is the CEO and co-founder of Priori, a legal marketplace that uses data instead of firm letterhead to match in-house teams with vetted outside counsel. She started the company in 2013 straight out of Yale Law School with classmate Mirra Levitt, at age 25 and with no business or technology background. A decade later she has raised more than $20 million, built a network spanning the $800 billion legal-services market, and become one of the most recognized voices arguing that how companies buy legal help is broken and fixable.