Jacob Kantor on why listening, trust, and grit matter in transforming education.
INTERVIEW | by Victor Rivero
When it comes to selling to school districts, Jacob Kantor doesn’t just talk the talk — he walks right through the door. Literally.
With more than 17 years of experience in education technology and roughly $50 million in cumulative sales, Jacob has become a trusted name across K–12 edtech. He’s led sales for top companies like McGraw Hill, Varsity Tutors, and Collegewise, and now consults with fast-growing names such as aiEDU, Stride K12, and Outlier. Through EDLIT — a platform he co-founded to connect edtech companies with district leaders in meaningful, non-sales conversations — he’s helping reshape how partnerships are built.
‘A crucial message for edtech founders: Prioritize educator collaboration. Seek substantive feedback, challenge assumptions, and design solutions that genuinely address educational needs.’
From his early days navigating L.A. school sites with MapQuest printouts to facilitating AI-powered pilots across rural America, Jacob’s journey is both impressive and deeply human. We sat down with him to learn more about his story, his insights into the evolving edtech landscape, and why he believes relationships — not just products — are what move the needle in K–12.
What inspired your entry into education and the edtech space?
As a first-generation immigrant who arrived in the United States from Ukraine at the age of five, I intimately understand the transformative power of education. My family’s narrative of resilience—exemplified by my brother’s leadership as an Emergency Room director—underscores the critical role educational opportunities play in immigrant success stories.
My professional trajectory in educational technology began in 2007, during the Great Recession, when I joined McGraw Hill as a per diem. Tasked with navigating the Los Angeles Unified School District’s (LAUSD) extensive network of 550+ elementary schools—a logistically complex assignment in the pre-smartphone era—I relied on nightly Mapquest route planning. This initial role rapidly evolved, and I was soon leading professional development training for the district’s English Language Arts program, Treasures.
How did those early experiences shape your sales approach?
The logistical challenges of working across such a massive district — especially before we had GPS and smartphones — taught me patience, resourcefulness, and the importance of face-to-face connection. Every school visit was an opportunity to learn and build trust, not just sell.
What differentiates effective education leaders in your experience?
Through my interactions with educational leaders and innovators, I’ve discerned a critical distinguishing characteristic: the most successful educators are those who demonstrate intellectual fearlessness. They are willing to implement potentially paradigm-shifting interventions, understanding that educational progress rarely occurs within perfectly aligned conditions. The only constant in education is perpetual change.
‘…the most successful educators are those who demonstrate intellectual fearlessness.’
What do you think holds back innovation in schools today?
Often, it’s a lack of support or misalignment between the solution and what educators actually need. Even well-intentioned tools can fail if they’re introduced without listening to the real, day-to-day challenges of teachers and administrators.
How can technology truly transform education?
Educational technology represents a powerful mechanism for pedagogical empowerment. When strategically implemented with rigorous fidelity, technological solutions can fundamentally alter student learning outcomes. However, this potential is contingent upon collaborative development—a principle often overlooked by technology companies that design solutions without substantive educator input.
HAPPY TO HOST. Jacob recently moderating a panel of key edtech leaders including Sophia Mendoza, Board Member ISTE+ASCD; Julia Fallon, Executive Director, State Educational Technology Directors (SETDA); and Patrick Gittisriboongul, Assistant Superintendent of Technology and Innovation, Lynwood Unified School District. The session was on, “Procurement for CTOs & District Leaders: The Good, The Bad, & The Ugly.”
Where do you see the biggest missed opportunities for edtech companies?
Not involving educators early and often in the product development process. Some of the most successful solutions I’ve seen are built alongside teachers, not just for them.
‘Some of the most successful solutions I’ve seen are built alongside teachers, not just for them.’
How would you describe today’s edtech landscape and its trajectory?
The current educational technology ecosystem presents both challenges and extraordinary opportunities. Despite diminished venture funding, innovative solutions are emerging that demonstrably improve student metrics. Companies like Tutored by Teachers exemplify impact-driven approaches, while others, such as Paper, illustrate the risks of solutions that lack student-centric design.
The advent of artificial intelligence represents a particularly transformative frontier. District leaders are increasingly seeking AI tools that can optimize administrative efficiency—with some aiming to reclaim up to one hour of daily operational time through strategic automation.
What are some encouraging trends you’ve seen recently?
My recent participation in the Education Accelerator Summit at Stanford University reinforced my optimism. Witnessing seventh-grade students conceptualizing impactful entrepreneurial ventures underscores the potential for innovation. The future of education belongs to those committed to meaningful, student-centered transformation.
Insights, Podcasts & Real Conversations That Move EdTech Forward. Jacob shares observations from interviews, panels, and conversations across the K–12 edtech landscape. Topics include current challenges, emerging practices, and how educators and companies are approaching technology, policy, and implementation in schools. LEARN MORE
What’s your advice for edtech founders trying to make an impact?
A crucial message for edtech founders: Prioritize educator collaboration. Seek substantive feedback, challenge assumptions, and design solutions that genuinely address educational needs.
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Victor Rivero is the Editor-in-Chief of EdTech Digest. Write to: victor@edtechdigest.com
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