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.
Resources Mentioned in this Episode:
Build vs. Buy Framework
Referenced during the conversation about opportunity cost, internal capacity, and helping districts evaluate whether it makes more sense to build solutions internally or partner externally.Summer School vs. Tutoring? What the Research Says
Nancy and Elana discuss how research around summer learning design, implementation, and outcomes can help districts better understand what drives impact and where common misconceptions still exist.Get in touch with Nancy: LinkedIn
Elana Leoni, Host
Elana Leoni has dedicated the majority of her career to improving K-12 education. Prior to founding LCG, she spent eight years leading the marketing and community strategy for the George Lucas Educational Foundation where she grew Edutopia’s social media presence exponentially to reach over 20 million education change-makers every month.
Nancy Livingston, Guest
As the CEO of NSSI, Nancy has over two decades of experience in driving academic excellence and talent development in K-12 schools. As the former Chief of Schools for KIPP Nashville, she oversaw the expansion of the network from five to seven schools while building the core infrastructure to support teaching and learning. At KIPP NYC, Nancy led a significant realignment of curriculum, assessment, and professional development strategies, resulting in substantial gains in student performance. Her career also includes leadership roles at Achievement First and KIPP Foundation, where she focused on scaling talent programs and academic systems. She was a founding teacher of KIPP Sunshine Peak Academy in Denver, CO and a TFA Corps Member in New Orleans. Nancy holds an MBA from the Yale School of Management and graduated Phi Beta Kappa and cum laude from Davidson College. She lives in Nashville, TN with her husband Steve and son Ulysses.
About All Things Marketing and Education
What if marketing was judged solely by the level of value it brings to its audience? Welcome to All Things Marketing and Education, a podcast that lives at the intersection of marketing and you guessed it, education. Each week, Elana Leoni, CEO of Leoni Consulting Group, highlights innovative social media marketing, community-building, and content marketing strategies that can significantly increase reach, relationships, and revenue.
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