He Stopped Climbing the Ladder and Built His Own Door episode artwork

EPISODE · Jun 26, 2026 · 54 MIN

He Stopped Climbing the Ladder and Built His Own Door

from Designing Schools · host Dr. Sabba Quidwai

Jacob Kantor was the number one sales rep everywhere he went - McGraw Hill, LAUSD, Varsity Tutors, Revolution Prep. He could have kept doing that forever. Instead, he created JK K12 Consulting and gave himself a title nobody had ever heard of: Chief DODO, which stands for District Office Door Opener.In this episode, we dig into what it actually took to design a career from scratch, why the best first meeting is one where you never mention the product, what the post-ESSER trust gap looks like from someone who sits between EdTech companies and district leaders every day, and how he built a weekly practice of giving people their flowers publicly on LinkedIn that changed everything.If you're a school or district leader, this conversation shows you what trust-building looks like from the other side of the table. If you're someone thinking about designing your own path instead of following a traditional one, Jacob's story is proof that it's possible, and that the messy middle is part of it.Dr. Sabba Quidwai is the CEO of Designing Schools and author of "Designing Schools: How Design Thinking Makes YOU Irreplaceable in the Age of AI." She works with schools and districts worldwide to help educators thrive in an AI-powered world.Jacob Kantor's website: https://thejacobkantor.comJacob on LinkedIn: https://www.linkedin.com/in/thejacobkantor

Jacob Kantor was the number one sales rep everywhere he went - McGraw Hill, LAUSD, Varsity Tutors, Revolution Prep. He could have kept doing that forever. Instead, he created JK K12 Consulting and gave himself a title nobody had ever heard of: Chief DODO, which stands for District Office Door Opener.In this episode, we dig into what it actually took to design a career from scratch, why the best first meeting is one where you never mention the product, what the post-ESSER trust gap looks like from someone who sits between EdTech companies and district leaders every day, and how he built a weekly practice of giving people their flowers publicly on LinkedIn that changed everything.If you're a school or district leader, this conversation shows you what trust-building looks like from the other side of the table. If you're someone thinking about designing your own path instead of following a traditional one, Jacob's story is proof that it's possible, and that the messy middle is part of it.Dr. Sabba Quidwai is the CEO of Designing Schools and author of "Designing Schools: How Design Thinking Makes YOU Irreplaceable in the Age of AI." She works with schools and districts worldwide to help educators thrive in an AI-powered world.Jacob Kantor's website: https://thejacobkantor.comJacob on LinkedIn: https://www.linkedin.com/in/thejacobkantor

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He Stopped Climbing the Ladder and Built His Own Door

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This episode was published on June 26, 2026.

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Jacob Kantor was the number one sales rep everywhere he went - McGraw Hill, LAUSD, Varsity Tutors, Revolution Prep. He could have kept doing that forever. Instead, he created JK K12 Consulting and gave himself a title nobody had ever heard of: Chief...

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