Summary
In this episode of the Madison Advisory AI Podcast, Amanda Verner Thompson sits down with Teresa Eng, a seasoned technology and operations leader with more than three decades of experience across product development, high tech, banking, and insurance.
Teresa shares what it actually looks like to lead digital and AI-driven transformation inside a small organization — where resources are limited, legacy habits run deep, and change is felt most acutely by people on the ground. Drawing from her work modernizing a 30-person insurance company, she explains why technology is often the easy part, and why culture, trust, and empathy ultimately determine whether transformation succeeds.
The conversation explores how leaders can move from AI overwhelm to clarity, why starting with the real problem matters more than choosing tools, and how building a strong data foundation enables smarter decisions over time. Teresa also reflects on mentoring, giving back, and what leadership looks like in uncertain economic and technological moments.
This episode is for leaders and operators who want practical, grounded insight — not hype — on how to navigate AI, change, and human behavior at the same time.
Takeaways
About the Guest
Teresa Eng is a business and technology leader with more than 35 years of experience spanning product development, high tech, and financial services. She currently leads technology and operations at Commercial One Insurance, a 30-person company in the commercial trucking space, where she oversees modernization, AI adoption, and cultural transformation.
Teresa is known for her emphasis on empathy as a leadership tool and her belief that while technology constantly evolves, culture and human behavior ultimately determine whether change sticks.
Connect with Teresa:
https://www.linkedin.com/in/teresa-eng-0b74537
About the Host
Amanda Verner Thompson is the founder of Madison Advisory AI, a firm positioned at the intersection of AI technology and seasoned advisory judgment. With nearly 20 years of experience as a healthcare investment banker, Amanda launched the Madison Advisory AI Podcast to explore how technology and AI intersect with real operations, real teams, and real human behavior — beyond the hype and buzzwords.
Each episode features thoughtful leaders navigating complexity and making decisions in rapidly changing business environments.
Learn more:
https://www.madisonadvisory.ai
Key Words
AI leadership, digital transformation, empathy in leadership, change management, insurance operations, small business transformation, data foundations, human-centered technology
