In this episode of The CTO Show with Mehmet, I sit down with Rob Duffy, CTO of HealthEdge, to unpack how healthcare—one of the last industries to modernize—is finally undergoing a deep digital transformation. Rob shares how his journey through companies like Amazon, Kindle, Time Inc., and Expedia prepared him for leading one of the most complex transitions in technology: taking healthcare systems from legacy mainframes to cloud-native platforms.

We discuss the hype vs. reality of AI, what true ROI looks like, and why cultural change is the hardest part of transformation. Whether you’re a tech leader, investor, or founder, Rob’s perspective sheds light on how to drive meaningful change in regulated and lagging industries.

Key Takeaways

• Why healthcare has lagged in digital transformation and how SaaS is shifting the landscape

• The real challenges of replacing mainframes and legacy systems in regulated industries

• AI in practice: from demos and hype to real ROI and human-hour savings

• Building an AI-first culture and making adoption stick inside organizations

• APIs, interoperability, and the future of system integration

• Career advice for aspiring CTOs: why learning the business matters as much as tech

What You’ll Learn

• How to navigate transformation in industries with entrenched legacy systems

• The single most important metric for measuring AI impact

• Why cultural adoption is the true unlock for enterprise AI

• How APIs and interoperability shape the future of healthcare and beyond

About the Guest

Robert Duffy is an accomplished technology leader with an extensive background in product development and engineering. Rob previously served as the Chief Product and Technology Officer at Drizly, an Uber Company, where he played a pivotal role in scaling the company’s product and engineering teams post-acquisition. His leadership at Drizly was instrumental in driving innovation within Uber Eats' grocery delivery services, showcasing his ability to merge technology with user-centric solutions. Prior to his tenure at Drizly, Robert held significant positions at industry giants including Salesforce.com, Amazon, and Time Inc.

At Salesforce, Rob excelled as the Vice President of Software Engineering, leading the team responsible for the Lightning Web Stack, which handles billions of API calls per day. At Time Inc, he served as VP of Engineering for its video and content platform that powered more than 300 content apps for 91 media brands with 139 million unique monthly users. At Amzaon, he was Head of Strategic Initiatives for the Kindle Store Platform, the content experience powering hundreds of millions of e-commerce transactions on the digital stores (books, audio books, video, and mp3) across all of Amazon's devices (fire tablet, kindle, echo, fire TV, and mobile apps).

https://www.linkedin.com/in/platformduffy/

https://healthedge.com/

Episode Highlights

• [02:30] Why healthcare is the last major industry to transform

• [06:45] Mainframes, legacy systems, and the cost of change

• [12:00] AI hype vs. real-world ROI examples

• [20:00] Building an AI-first culture and driving adoption

• [27:30] Governance, security, and evaluating new AI tools

• [33:00] Pilot programs and scaling cultural change

• [38:00] AI’s role in cloud optimization and legacy refactoring

• [44:00] APIs as the next big unlock for enterprise systems

• [46:30] Rob’s advice for aspiring CTOs: learn the business first