Fighter Jets, Fintech, and the Frontier of AI: Mastering the Art of Adaptable Leadership with Gregory Gorman

In an era when artificial intelligence is reshaping entire industries and the pace of software innovation feels almost unmanageable, the question of leadership—what it looks like, how it adapts, and who embodies it—has never been more vital. The technology sector is confronting one of the fastest paradigm shifts in decades, and with that change comes a demand for leaders who can inspire resilience, adaptability, and purpose amid uncertainty.

So, how does a modern leader guide technical teams through seismic transformation without losing sight of human connection?

Welcome to Crafted Journeys, brought to you by Digital Artisans. In the latest episode, host Suzy DeLine sits down with Gregory Gorman, ESEP, Director of Developer Relations at PayPal, to explore a career that spans fighter jets, fintech, and the frontier of AI. Together, they unpack Gorman’s evolution from electrical engineer at McDonnell Douglas to developer advocate and executive leader—revealing the craftsmanship behind decades of technological and personal growth.

Highlights from the conversation…

Resilience as a leadership skill: Gorman explains why adaptability—honed through decades of change from defense tech to digital payments—is a leader’s greatest tool.

Engineering precision meets human empathy: From cockpit systems to PayPal’s developer relations, he draws parallels between software reliability and trust in people.

AI and influence: Gorman shares PayPal’s pioneering efforts to ensure AI systems like ChatGPT accurately represent company data—showing how influence and integrity intertwine in the age of large language models.

Gregory Gorman, ESEP, is a seasoned technology executive and systems engineer with more than three decades of global experience across aerospace, enterprise software, and fintech. As Director of Developer Relations at PayPal, he leads initiatives that connect developers with innovation at scale. Before joining PayPal, Gorman spent 14 years at IBM, where he guided developer ecosystem strategy, oversaw site infrastructure and security, and helped launch the pioneering Watson IoT business unit. His earlier career included leadership roles at Telelogic, Honeywell, and McDonnell Aircraft, where he directed teams building mission-critical software for commercial and defense aviation systems.

Article written by MarketScale.