Once: Cracking the Six-Figure EdTech Enterprise Sale with Matt Pasternack

Join Pete in conversation with Matt Pasternack, Founder of Once, who's built a $2M+ ARR company selling high-ticket reading intervention programs to the nation's largest school districts.Matt reveals how he navigated the high-stakes education sales landscape by creating artificial compelling events through academic research partnerships - an ingenious approach that generated a 10% positive response rate from typically unresponsive district leaders.Pete and Matt dissect why selling to individual principals was abandoned despite impressive open rates, why Once exclusively targets the top 500 districts with six-figure deals, and the fascinating "trust importation" strategy that unlocked enterprise sales when Matt's own EdTech credentials weren't enough.The conversation highlights the stark differences between selling EdTech to IT departments versus academic officers - including how misunderstanding a single term like "authentic reading" can immediately end a sales conversation.Once's high-touch, relationship-driven approach has powered them to mid-six figure deals with a lean three-person sales team, proving that in education, trust and relationships trump traditional sales tactics.More on Once here: https://www.tryonce.com/ Sales motion details: Reading tutoring upskilling service, Top 500 district targets, Chief Academic Officers and principals as buyer personas, mid-five to mid-six figure ASP, 12+ month sales cycle with year-long validation periods.