Return of the CTO: Inside Conor Sibley’s AI-Driven Comeback

In this powerhouse episode of Software Leaders Uncensored, host Steve Taplin sits down with Conor Sibley, the returning CTO of Higher Logic, to unpack why he left—and then rejoined—the company he helped scale. Conor dives deep into what it takes to run a 75+ person engineering team, his approach to enterprise-wide AI transformation, and how his angel investing background shaped his strategic mindset. From AI-powered documentation to turning LLMs into productive team members, Conor lays out a clear blueprint for the future of software development. He doesn’t mince words either: “AI or die.” This episode is a must-listen for engineering leaders, SaaS operators, and innovators navigating the AI revolution.