Selling into schools is rarely as straightforward as most teams expect.

District leaders are navigating competing priorities, long approval cycles, staffing challenges, and increasing pressure to justify every decision. At the same time, EdTech companies are trying to build trust, move deals forward, and prove their value in a crowded market.

Nancy Livingston, CEO of the National Summer School Initiative (NSSI), joins Elana for an honest conversation about what actually drives K-12 purchasing decisions and why so many organizations misunderstand the realities of selling into education.

Drawing from experience on both sides of the table, Nancy shares what surprised her most after moving from district leadership into sales, where deals typically stall, and why trust-building looks very different in education than in other industries.

The conversation explores the tension between empathy and momentum, the hidden complexity of procurement, and the role marketing plays in helping districts feel informed, confident, and ready to move forward.

If your team is trying to better understand how decisions really happen inside schools, this episode offers a grounded look at the process behind the partnership.

What You’ll Learn

Why K-12 sales cycles are far more complex and relationship-driven than most teams expect
How empathy, trust, and timing shape whether deals move forward or stall out
Why the status quo is often a stronger competitor than another vendor
What district leaders actually look for before committing to a partnership
How procurement, funding structures, and internal approvals quietly influence decision-making
The role marketing plays in building credibility long before a sales conversation begins

Why it Matters

Too many organizations approach education sales as a faster-moving commercial process. But school systems do not make decisions in isolation, and they rarely move quickly without trust, alignment, and internal clarity.

Nancy’s perspective is a valuable reminder that successful partnerships are built through patience, responsiveness, and a real understanding of how districts operate. For marketers especially, this shifts the work away from pushing urgency and toward creating the kind of credibility and education that helps decisions move forward over time.