Rob Saccone
Legal tech builder and operator with ~25 years in the industry, focused on applied AI in the legal space and experience as a founder, advisor, and C-suite executive.
Best podcasts with Rob Saccone
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Mar 23, 2026 • 50min
[LIVE] Dissecting the Claude Legal Plugin: A Live Technical and Legal Teardown
Josh Kubicki, lawyer, law professor, and AI practitioner, and Rob Saccone, legal-tech builder and operator with ~25 years of experience, open the Claude legal plugin and dissect its 200-line playbooks. They walk through the NDA skill files, compare plugin outputs to raw model outputs, run cross-model skill checks, and debate security, local file access, and how playbooks scale for legal triage.
Oct 8, 2025 • 48min
89 - Legal Innovation Lessons: What Works, What Doesn't, and Why with Rob Saccone
Rob Saccone, CTO at Lega and a legal tech veteran with over 25 years of experience, shares invaluable insights on the lessons learned from failed innovations like Clearspire and Atrium. He emphasizes the importance of adapting law firm business models to client needs and the pressures AI places on traditional billing. Discussing the challenges of alternative fee arrangements, he warns of the risks of not investing in innovation. Rob also explores the potential of practical Gen AI deployments and the need for a shift in partnership mindsets to foster growth.
