Ep # 187: 97% Trial-to-Paid, 21-Day Sales Cycles, and the New SaaS ROI Bar ft. Sara Wyman (CEO, Stackpack)

In this episode of Across The Funnel, Adil Saleh sits down with Sara Wyman, Founder & CEO at Stackpack, to explore how vendor management is changing as companies deal with AI spend, tool sprawl, renewal pressure, and the need for clearer ROI. Sara explains why finance teams are often the first wedge into an account, how Stackpack helps customers get fast visibility into contracts and spend, and why usage, engagement, and data under management are the clearest signs that a customer is getting value. The conversation also covers trial-to-paid conversion, close velocity, pricing shifts toward usage-based models, the growing messiness of the AI vendor market, and why human judgment still matters even as teams use AI to move faster. It is a practical episode on post-sale value, retention, expansion, and how modern B2B teams should think about software buying and customer adoption in an increasingly noisy market.