The Transformation Trap: Why Software Modernization Is Harder Than It Looks

Screaming in the Cloud

In this episode of Screaming in the Cloud, Corey Quinn talks with Jonathan Schneider, CEO of Moderne and author on Java microservices and automated code remediation. They explore why upgrading legacy systems is so hard, Schneider’s journey from Netflix to building large-scale code transformation tools like OpenRewrite, and how major companies like Amazon, IBM, and Microsoft use it.

They also discuss AI in software development, cutting through the hype to show where it genuinely helps, and the human and technical challenges of modernization. The conversation offers a practical look at how AI and automation can boost productivity without replacing the need for expert oversight.

Show Highlights

(2:07) Book Writing and the Pain of Documentation

(4:03) Why Software Modernization Is So Hard

(6:53) Automating Software Modernization at Netflix

(8:07) Culture and Modernization: Netflix vs. Google vs. JP Morgan

(10:40) Social Engineering Problems in Software Modernization

(13:20) The Geometric Explosion of Software Complexity

(17:57) The Foundation for LLMs in Software Modernization

(21:16) AI Coding Assistants: Confidence, Fallibility, and Collaboration

(22:37) The Python 2 to 3 Migration: Lessons for Modernization

(27:56) The Human Element: Responsibility, Skepticism, and the Future of Work

Links

1. Crying Out Cloud Podcast & Newsletter: https://www.wiz.io/crying-out-cloud
2. Modern (Jonathan Schneider's company): https://modern.ai
3. LinkedIn (Jonathan Schneider): https://www.linkedin.com/in/jonathanschneider/