3244: From Mainframes to AI: Paula Paul on Building Software That Lasts

What happens when four decades of hands-on engineering experience meet today’s fast-moving AI and open-source ecosystem?

In this episode of Tech Talks Daily, I sit down with Paula Paul, Founder and Distinguished Engineer at Greyshore, to explore that intersection. Paula began her tech career in the early 1980s writing code for IBM mainframes and has since become a trusted voice in enterprise modernization, cloud adoption, and open-source governance. Today, she advises organizations on how to build with confidence in an era defined by complex software supply chains, generative AI, and evolving SaaS models.

We recorded this conversation during a time when many organizations are feeling the pressure to adopt AI and modernize legacy systems, but struggle with where to begin. Paula offers grounded insights on how to break down replatforming into value-driven streams and why a “big bang” transformation approach is often more risk than reward. She also talks about the critical role of open source in business today—not just from a tooling standpoint, but in terms of responsibility, transparency, and community.

Paula’s perspective is refreshingly practical. She believes AI is a natural evolution of decades of computing and storage expansion but urges companies to start with targeted experiments and thoughtful team collaboration. She also shares her experiences as a woman in tech since the 1980s, reflecting on what’s changed and what hasn’t and how leadership dynamics continue to shape opportunities for women in the industry.

Beyond the code, Paula draws a fascinating parallel between music and technology. As a board member of the Brookline Music School and an oboe and English horn student, she explores how musical thinking can enhance software development's rhythm, structure, and leadership.

If you’re navigating modernization, curious about AI’s role in development, or wondering how to make open source work for your organization—technically and strategically—this episode has something for you. How are you balancing technical ambition with long-term value? Let’s continue the conversation.