Leading Legal in a Product-Led Company

Summary In this episode of Uplevel View, Stephanie Corey sits down with Betsy Cantrell, VP of Legal at HighLevel, to explore how legal teams must evolve in fast-moving, product-led organizations. Betsy shares her journey from a highly structured corporate legal environment at Intel to building a scrappy, agile legal function from scratch in a startup. The conversation dives into how legal teams can move from being perceived as blockers to becoming strategic partners embedded within product development. Key themes include integrating legal into product workflows, hiring adaptable talent, leveraging legal operations, and—most critically—embracing AI as a core driver of efficiency, scalability, and relevance. Betsy emphasizes that the biggest risk today isn't using AI imperfectly—it's not using it at all. This episode is a must-listen for legal leaders looking to modernize their function, scale effectively, and stay ahead in an AI-driven world. Links & Resources UpLevel Ops: http://UplevelOps.com Above The Law: http://AbovetheLaw.com Keywords Legal Operations, Product-Led Companies, In-House Counsel, AI in Legal, Legal Tech, Startup Legal, Compliance, Privacy Law, Workflow Automation, Legal Strategy, General Counsel, Legal Innovation, AI Adoption, Corporate Law, Legal Leadership 🎧 Episode Highlights (with timestamps) 00:00–00:33 – Why legal involvement often comes too late in product-led companies 01:13–01:49 – Betsy's journey: from Intel to building a startup legal team from scratch 02:18–03:05 – The cultural shift: from legal authority to proving value 03:05–04:08 – Why legal must understand product and user experience 05:33–06:31 – Hiring for startups: curiosity over specialization 06:53–07:48 – Learning new legal domains (like privacy) on the fly 08:06–08:47 – Why the first hire was legal ops—not a lawyer 11:01–11:27 – The power of exposure and learning across domains 12:21–13:05 – Using competitors and AI as benchmarks for decision-making 15:13–16:11 – Embedding legal into product workflows without friction 16:55–17:34 – Using AI agents to flag legal risks automatically 20:29–20:45 – Why complex intake forms fail 21:37–22:28 – AI agents replacing repetitive legal review work 23:30–24:13 – The real risk: not adopting AI fast enough 27:01–27:43 – AI as a headcount multiplier for legal teams