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Legacy B2B software wasn’t built for how teams work today. And that gap is what creates slow adoption, poor outcomes, and failed implementations. In this episode of The SaaS Playbook, Jenny Vo speaks with Dan Koukol, Co-Founder & CEO of Digit Software, about what causes legacy systems to fail and how SaaS leaders can build better products by focusing on usability, configurability, and customer outcomes. Drawing from years of consulting and operating experience, Dan explains why many systems promise simplicity but deliver complexity, and how leadership decisions shape product success long before code is written. In this episode, we cover: • Why legacy systems fail in modern SaaS environments • How leadership responsibility shapes product direction • Designing configurable software for real-world operations • Turning data into proactive insight with AI • Measuring success through customer outcomes, not vanity metrics • Scaling product depth without sacrificing usability This episode is designed for SaaS founders, product leaders, and B2B operators building software meant to scale in complex industries. 👇 Episode discussion and insights are in the comments Dan's Links: LinkedIn: / danielkoukol Digit: https://www.digit-software.com/ Music from #Uppbeat https://uppbeat.io/t/abbynoise/shocki... License code: N2PYVKCFUCMJNN6G