Tim Heicks talks with me about my early days in SaaS, the evolution of PLG and enterprise software, and my journey to Winning by Design. We also discuss my book on PLG, new perspectives on freemium, and how AI is changing GTM — from human touch to search and discovery — as well as what I look for when evaluating companies for acquisition.
Episode Breakdown
00:00 – Introduction and guest background
01:11 – Early days in SaaS and entrepreneurship
03:13 – Evolution of PLG and enterprise software
06:13 – Joining Winning by Design
09:11 – Writing the PLG book for the masses
12:19 – Consulting and value add for companies
16:00 – New perspectives on PLG and freemium
23:06 – AI’s impact on GTM and human touch
31:16 – AI search and the future of discovery
36:03 – Evaluating companies for acquisition