Arjun Pillai and Stevie Case unpack what’s working right now in B2B GTM and what breaks as you scale. Stevie shares how the CRO role evolves over time at Vanta, expanding from sales to owning the full customer journey globally. She gives a grounded definition of product-market fit: it’s not an ARR milestone, it’s something you can hear in customer conversations, and if you’re constantly fighting for dollars, PMF likely isn’t there yet.

They dig into pipeline evolution, including why inbound is powerful early but has a ceiling, and how Vanta built a true outbound engine by scaling SDR capacity and operationalizing new messaging, methodology, and AE-SDR collaboration. Stevie also makes a clear case for cold calling, especially for early-stage companies with limited awareness, as long as the outreach is thoughtful and informed. Finally, she outlines Vanta’s AI approach: use AI to supercharge reps by automating prep, follow-ups, and repeatable workflows, then democratize top-performer plays and enable teams to build their own agents.