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