In this episode of Across The Funnel, Adil Saleh sits down with Kyle Racki, Co-Founder and CEO of Proposify, and Proposify to explore why proposals remain the “digital handshake” in mid-market and enterprise sales, what teams actually buy proposal software for (speed, consistency, fewer errors, better buyer visibility), and how this category is evolving alongside contracts, CPQ, CLM, and digital sales roms. Kyle shares how Proposify navigated SaaS market cycles, moved from early scrappiness to raising capital, then returned to a profitability-first operating style, plus why adding products matters when markets are big but not infinite. He and Adil also pressure-test the AI hype, including the Dunning–Kruger trap where “easy to build” often means “easy to build something fragile,” and they connect that to real-world product work like tech debt, replatforming, and why Proposify 3 existed as a reset for modern shipping speed. On the customer side, Kyle walks through onboarding and time-to-value, including a candid example where an AI template generator hurt conversions because it was slow and produced mediocre outputs, which pushed the team toward simpler AI uses and a more reliable services-led “launch kit” to get customers live faster with the right setup, guidance, and early support.