In this pop-up podcast episode from Imagine AI Live 2025, Chris Madden sits down with Navin Jenovathas, Head of Revenue at Expertise AI (formerly Chatsimple). They dive deep into how the company is reinventing inbound sales using contextual AI, de-anonymizing web traffic, and creating custom conversational journeys based on user intent and role. Navin breaks down how Expertise AI helps companies turn passive website visits into qualified pipeline using a smart, adaptive interface. From tailoring conversations for CEOs, sales heads, and marketers — to surfacing microsite content dynamically within chat — this episode explores the real future of AI SDRs. You’ll also hear insights about platform consolidation, vendor bloat, and leaving a legacy through tech. (0:00) Welcome & Introductions (1:20) Why marketing traffic isn't enough (3:12) Adaptive UI that personalizes by buyer role (4:28) Moving toward a unified sales platform (5:21) The unique vibe at Imagine AI Live (6:08) Empowering solopreneurs to leave a family legacy (6:40) Where to find Expertise AI