Eric Westendorf is an unlikely tech entrepreneur. Back in 2011, he was chief academic officer of the E. L. Haynes Public Charter School in Washington, D.C. Teachers at the school kept telling him that they needed better ways to help struggling students catch up on lessons that other students had mastered. There just aren’t enough hours in the day to meet every student’s individual needs, the teachers told him. So he created LearningMatch, a tool that allows teachers to record and share...

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