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.

In this candid episode of Software Leaders Uncensored, host Steve Taplin talks with Matthew Mixan, CTO of Decision Logic, about scaling SaaS in the high-stakes world of restaurants. Matthew opens up about his journey from writing code in the '90s to leading a 20-person engineering team today. He discusses why communication beats raw coding talent, how Decision Logic empowers restaurants with inventory, staffing, and AI-driven forecasting tools, and why he passed on launching his own SaaS startup to take the helm of one already poised for growth. If you're navigating product scalability, team dynamics, or AI integration in real-world tech, this episode delivers clarity and inspiration.

In this raw and insightful episode of Software Leaders Uncensored, host Steve Taplin sits down with Jason Tesser, a five-time founder and now CTO/ VP of Engineering at Revvable, to discuss the highs and lows of engineering leadership. Jason shares lessons from his 25-year tech journey, including why data engineering is often the Achilles’ heel of scaling software, how he rebuilt Revvable’s dev team with clear roles, and how a simple autofill Chrome extension disrupted an overlooked industry. Plus, he opens up about job market struggles—applying to 450 roles before finding the right fit—and the importance of staying hands-on, even at the top.