The best leaders don’t just solve problems; they fix the system.

In this episode, Aaron Kopel sits down with Earl Shaw, CIO at Renaissance Benefits & Health Insurance, to talk about what it really takes to rebuild trust and performance within an organization under pressure. Earl discusses how his love for strategy and puzzles shaped his leadership style, and how embracing unfamiliar opportunities made him a more well-rounded enterprise leader.

Earl also shares his take on what stays the same and what changes in an AI-driven world. He highlights why communication and change management are key, as tools like Microsoft Copilot reshape work, and why top technologists need more than just technical skills. In this conversation, Earl shows that momentum ultimately comes from clarity, curiosity, and the discipline to fix the system.

Key takeaways:

• Great leaders solve challenges like puzzles with critical thinking and strategy
• Communication builds trust faster than speed alone
• Liberal arts, like critical thinking, storytelling, and communication, are just as essential for shaping well-rounded IT leaders

Episode highlights

(00:00) Intro

(01:04) Key moments that shape leadership

(05:25) How listening and innovation turned IT services around

(13:11) Why liberal arts matter for technologists in the AI age

(17:47) The power of storytelling in technology

(20:04) How AI is accelerating business growth and innovation

(23:51) Why knowing every aspect of the organization powers technology success

(25:52) Rapid-fire questions

(32:31) Why curiosity and adaptability matter in tech leadership

Earl Shaw on LinkedIn: https://www.linkedin.com/in/earl-shaw/ 

Aaron Kopel on LinkedIn: https://www.linkedin.com/in/aaronkopel

Explore Renaissance Benefits & Health Insurance: https://renaissancebenefits.com/ 

Explore Project Brilliant: https://projectbrilliant.com

The Science of Scaling by Benjamin Hardy: https://a.co/d/76xHeGD 

Buy Unlocking Momentum: https://a.co/d/hKPFqoS