Episode 42: From Fear to Fluency: VP Andy Vitale on How to Lead AI Innovation with Confidence

Andy Vitale has been building with AI since 2015, across healthcare, banking, mortgage, marketing, and now tax software, long before it became a leadership talking point. He was auto-suggesting medical codes at 3M before most people knew what machine learning was. He helped increase loan volume at Rocket Companies by billions of dollars through conversational AI. And now, as VP and Head of Product Design and AI Center of Excellence at TaxWell, he is shipping AI-powered features within a single tax season while spending 75% of his week in AI-related work, at the VP level, hands-on. In this conversation, we trace that full arc: what it looked like to build with AI before it was a trend, how product teams are working differently now, why design systems have become a competitive moat, and what separates the leaders who will thrive in this moment from the ones who quietly become speed bumps. If you have been feeling the pressure to get fluent in AI and lead your team through a transition you are still figuring out yourself, this episode is worth a listen. REFERENCES:Claude: https://claude.aiWisprflow: https://wisprflow.aiFigma Make: https://www.figma.com/make/Cursor: https://cursor.com/ CONNECT WITH ANDY: LinkedIn: https://www.linkedin.com/in/andyvitale/ Website: https://www.andyvitale.com/ Design Executive Council: https://www.designexecutivecouncil.com/ CONNECT WITH KRISTIANA: Website: https://www.worthytolead.co/ LinkedIn: https://linkedin.com/in/kristianacorona Instagram: https://www.instagram.com/worthytolead/ Substack: https://worthytolead.substack.com/