In this episode of All Things Marketing and Education, Elana Leoni talks with Jacob Kantor—a former district insider turned EdTech consultant—about how companies can stop being ignored and start being trusted. Known as the “Chief DODO” (District Office Door Opener), Jacob has built his career on bridging the gap between solution providers and the educators they’re trying to serve.
With humor and honesty, Jacob breaks down what most EdTech teams get wrong when trying to connect with district leaders (and how to flip the script). Instead of pushing products, he champions a human-centered approach built on listening, curiosity, and real follow-through. From prepping before meetings to sending thoughtful, non-transactional follow-ups, Jacob explains how to build relationships that lead to long-term partnerships that go beyond short-term sales.
Together, Elana and Jacob explore:
Why leading with curiosity and empathy beats pushing a product
How to write outreach emails that district leaders actually want to read (and why naming the pressure they're under matters)
What most vendors misunderstand about administrators’ day-to-day pressures—and how to reframe your first call to serve them
Why implementation misalignment breaks trust, and how to avoid it by knowing who actually uses your product
The powerful influence of behind-the-scenes word-of-mouth, and how to earn a good reputation without even realizing it
This episode is packed with tactical advice, hard-earned wisdom, and gentle reminders that relationship-building is the most strategic move EdTech companies can make.
🎧 Plus: Why simply following up after a great conversation (without selling) can be the easiest way to build trust with a district leader. Jacob shares how he uses warm, low-pressure follow-ups to stay top of mind and turn one good meeting into a long-term relationship.
Resources Mentioned in this Episode:
Mentioned for social selling strategies on LinkedIn. Jacob’s approach echoes some of these techniques.
Referenced as a model for strong district relationships and educator engagement. Jacob highlights a 3-hour webinar with high administrator turnout as a sign of trust and partnership.
The 4-Hour Workweek by Tim Ferriss
Jacob mentions Ferriss’s outreach experiment with students emailing high-profile people to push past fear of rejection.
Matt Tower / Whiteboard Advisors
Referenced for his EdTech funding trend analysis—particularly around AI investment.
Nonprofit mentioned for leading AI literacy efforts in K–12. Jacob talks about Alex Coran and their early work before ChatGPT’s popularity.
AIEDU’s Free AI Literacy Curriculum
This resource includes free classroom-ready lessons designed to help educators teach students the fundamentals of artificial intelligence. Ideal for middle and high school settings, it's a nonprofit-backed toolkit created with both teachers and equity in mind.Putting AI to Work in Schools Is Difficult. A New Toolkit Outlines How to Do It
New toolkit from Education Week offers practical guidance for school and district leaders navigating how to use AI effectively and ethically. It’s a must-read for anyone serious about supporting educators through smart, human-centered adoption.Get in touch with Jacob: 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.
Jacob Kantor, Guest
In my 17 years, I have been THE sales guy who has always captured the top spot.
Places I've worked....
LAUSD
McGraw Hill
C2 Education
Revolution Prep
Collegewise
Spark Education
For the last 2+ years I started JK K12 Edu (Consultancy) & coined myself as Chief DODO - District Office Door Opener. Full-time Consulting Clients Include, but aren't limited to - Stride K12, aiEDU, Outlier (sold to Savvas), Gladeo, Singleton Foundation for Financial Literacy and Entrepreneurship, Virtu Academy, IEP&me , Frenalytics , Slyngshot , READ , Physics Wallah , Toddle
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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