Jerry Levine

Chief Evangelist and General Counsel

Jerry Levine is the Chief Evangelist and General Counsel at Leah (formerly ContractPodAi), a globally recognized legal technology leader with nearly two decades of experience at the intersection of law, AI, and digital transformation — work that earned him recognition as a Top USA General Counsel by Legal500. Over the past year, Jerry has steered the company through a complete rebrand from ContractPodAi to Leah ("a bit like renovating your house while still living in it"), reinvigorated its partner ecosystem through new deal structures and collaboration frameworks, and led a series of internal standardization projects that turn the company's own tools on itself. A vocal proponent of human-first AI, he champions a trust-by-design philosophy in which explainable models, risk-based delegation, and strong data governance enable legal teams to move faster without sacrificing judgment, accountability, or compliance with evolving data protection laws. Jerry sees the modern legal leader as a "student of the future" — strategic not by virtue of being in the room when documents are signed, but by earning enough trust to be there when decisions are made, asking uncomfortable questions about efficiency, automation, and even the nature of legal work itself. Looking ahead, he is closely tracking how agentic AI is reshaping legal talent strategies, dissolving traditional boundaries between legal, compliance, and technology, and elevating a new generation of lawyers fluent in data, judgment, and cross-disciplinary collaboration. Based in the NYC area, Jerry is a sought-after speaker and writer for publications, podcasts, webinars, and industry events, where his sharp, witty, and direct voice translates complex legal-tech ideas into practical guidance for in-house teams navigating a rapidly changing profession.