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In this webinar, we explore how real General Counsels (GCs), including George Hypolite (New Mexico Department), are using AI and legal automation to scale legal operations, reduce manual work, and drive real change. In this video, we explore: Why legal departments must treat their tech stack as a strategic roadmap — not just a reaction to immediate problems How to navigate overlapping tools in the legal tech market (e.g., CLM, ELM, workflow automation) The pitfalls of “one system to rule them all” and why the best legal ops teams pursue a rationalized, hybrid tech approach How to frame legal tech needs using IT's language (e.g., business capability models) to win buy-in Real-world advice on managing IT pushback and articulating legal-specific functionality (intake, matter management, NDA workflows, document-heavy processes) Lessons on avoiding “application proliferation” while still addressing nuanced legal team needs Whether you’re leading legal operations or planning your department’s tech roadmap, this conversation offers actionable insights to help you balance innovation, budget, and enterprise alignment. #legaltechnology #legalsolution #legaltech #legalops #legalautomation ⏱️Timestamps 00:00 – Introduction by Evan Wong, CEO of Checkbox 01:05 – Meet George Hypolite: From NFL to General Counsel 02:40 – Story behind “The Rabid Goldfish” nickname 04:25 – Setting the scene: Why legal teams are turning to AI & legal automation 06:04 – Introduction to Legal Automation and Agile Methodologies 07:09 – Communication and Flexibility in Legal Process Automation 09:32 – The Economics of AI vs. FTEs in Legal Departments (Legal Automation Software ROI) 12:21 – Efficiency and Empowerment through Legal Tech AI 13:56 – Prioritization and Sponsorship of Legal Technology Solutions 15:00 – Overcoming fear: Will legal automation software replace jobs? 18:00 – Why AI augments legal professionals (not replaces them) 20:39 – NDA Automation Process and Live Demo (Legal Workflow Automation in action) 22:00 – “AI Literacy” and Training Teams to Use Legal Technologies 26:00 – Encouraging AI Use in Legal Operations While Setting Guardrails 30:00 – What Legal Tech AI Can (and Can’t) Do Well Today 32:08 – Continuous Integration, Feedback, and Legal Operations Software Improvement 36:00 – Legal Document Summarization & Research (Future of Legal Technology) 40:00 – Research Tools, Verifying AI Output, and Legal Technology Solutions in Practice 44:10 – Importance of Strong Use Cases in Legal Tech Innovation 47:00 – Final Thoughts on the Future of Legal and Digital Transformation in Legal Teams 🎉 Where to find Checkbox • Website: https://www.checkbox.ai/ • Twitter: / checkboxai • LinkedIn: / checkboxai 🔗 Other Resources https://www.checkbox.ai/in-house-lega...