VC 2: How Cassie Young Picks Winners Before They Even Leave Their Jobs

Episode notes

Cassie Young is a General Partner at Primary Venture Partners, a $1B AUM early-stage firm in New York backing category-defining SaaS, fintech, and vertical software companies. Before investing, she spent 15 years as a GTM operator, serving as Chief Revenue Officer at Sailthru and later Chief Customer & Commercial Officer at Marigold (Campaign Monitor, Sailthru, and other martech brands), where she scaled global sales, marketing, and customer success organizations. Today, Cassie leads investments while also running Primary’s Impact program, giving founders access to a 30-person team across talent, GTM, and strategic finance, and she continues to teach operators through programs like Pavilion and Duke’s Innovation & Entrepreneurship board. Discussed in this episode: How Cassie “accidentally” became a VC after 15 years in GTM leadership. The career advice Bill Gurley gave her that changed her trajectory. Why Primary refuses to say “platform” and instead built a 30-person Impact team. How she actually sources pre-seed/seed founders before they leave their jobs. Primary’s 5-part Founder Outcomes Framework (vision, talent, JDCE, and more). The difference between real traction vs.