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

What happens when a technologist chooses public service and discovers leadership is less about systems and more about people?

In this episode, Aaron Kopel sits down with Collin Hill, CIO of Indianapolis and Marion County, to explore how service industry experience, local government work, and calm leadership under pressure shape stronger technology leaders. Collin shares his unexpected path into public service and why running technology for his hometown has become the most challenging and rewarding role of his career.

The conversation explores a pivotal moment early in Collin’s CIO journey, when a cybersecurity initiative triggered backlash across the organization and forced a defining leadership choice. Rather than retreating, he leaned in, making a decision that reshaped how security and shared responsibility showed up across the city. He also shares why service industry experience builds the empathy and steadiness needed to lead tech teams under pressure.

Key takeaways

• Service industry experience builds empathy and stronger leadership skills
• Local government offers unmatched responsibility and community impact
• Effective CIOs lead with calm communication and a people first mindset

Episode highlights

(00:00) Intro

(01:50) When playing it safe stops working

(04:39) Why everyone should spend time in local government

(10:45) How working in the service industry makes the best talents

(15:42) Culture is set in the most uncomfortable moments

(19:48) When you have to stand on what you believe

(21:03) Running technology for your own hometown

(23:07) Rapid fire questions

(27:45) Leaving the world better than when you found it

Resources

Collin Hill on LinkedIn: https://www.linkedin.com/in/collin-hill-b178483/
Aaron Kopel on LinkedIn: https://www.linkedin.com/in/aaronkopel

Explore the Information Services Agency of the City of Indianapolis and Marion County: https://www.indy.gov/agency/information-services-agency

Explore Project Brilliant: https://projectbrilliant.com

Explore the Indiana CIO Network: https://techpoint.org/indiana-cio-network/

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

Why should CIOs step away from being the "technical fixer" to lead effectively?

In this episode, Aaron Kopel sits down with Jeff Ton, former CIO of Ton Enterprises, LLC, and a seasoned leader in IT and leadership development. Jeff shares his journey from COBOL punch cards to guiding leaders on transformative expeditions inspired by the Lewis and Clark trail. He explains why leadership is about more than just technical skills and how understanding core values can shape a team’s vision.

Leadership comes with both challenges and rewards, and Jeff explores what it really takes to guide a team. He shares how experiences, even a nature expedition, can offer fresh perspectives and reshape the way leaders see their role.

Key takeaways

• Leadership is about enabling others, not just controlling outcomes
• Strong communication builds trust and drives alignment within teams
• CIOs who focus on people and vision, not just the tech, make the biggest impact

Episode highlights

(00:00) Intro

(01:10) How prioritizing the right projects transforms IT momentum

(06:45) AI as a tool for transformation, not a one-size-fits-all solution

(13:44) On leadership, writing, and walking the Lewis and Clark Trail

(19:11) How to navigate leadership with a balanced perspective

(24:09) Lessons on tech and music

(27:56) Rapid-fire questions

Resources

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

Explore Ton Enterprises, LLC: https://jeffreyston.com/

Explore Project Brilliant: https://projectbrilliant.com

Explore the Indiana CIO Network: https://techpoint.org/indiana-cio-network/

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