former-teacher
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Robin Sykes Still Counts in Bear Bucks
Before she led global brand and growth at Securly, Robin Sykes ran an elementary school's reward economy with hand-cut paper. Her career is a lesson in carrying classroom evidence into the boardroom.
Jeff Scheur Graded 15,000 Papers. Then He Rebuilt the Feedback Loop.
A Chicago English teacher turned a 2 a.m. grading ritual into NoRedInk. His enduring idea is disarmingly practical: software should give students room to practice and give teachers more time to teach.
The Teacher Who Kept Marketing to Teachers
He taught eighth grade for nine years and was named Teacher of the Year. Then he spent the next two decades convincing the world's biggest education brands to market like they still remembered the classroom.
Andrew Rowland
Andrew Rowland is the founder and CEO of Classkick, a Chicago-based education technology company whose real-time digital notebook lets teachers see every student's work as it happens and respond instantly with notes, audio, or chat. A former Chicago high-school math teacher known to his students as 'Mr. Roro,' Rowland taught through Teach for America and started a school robotics program before retraining in computer science and working at Google and YouTube. He built Classkick to scale the thing he loved most about teaching: the 'aha' moment and the fast feedback loop. The platform now reaches more than half of U.S. schools and students in 180-plus countries, running on Firebase infrastructure.
Jake Sussman
Jake Sussman is the cofounder and CEO of Marble Health, a virtual behavioral health company that embeds inside American schools to get anxious, depressed and overwhelmed kids into group therapy within days rather than months. He helped build Headway into a mental-health unicorn, then walked away to teach fifth-grade English at a Brooklyn charter school, where one overstretched counselor for hundreds of students convinced him the youth side of the system was broken. In 2023 he founded Marble with fellow Headway alum Dan Ross, betting that insurance-funded virtual group therapy, routed through school counselors, could scale care without waitlists. By late 2025 Marble had run more than 15,000 sessions and raised a $15.5M Series A led by Costanoa Ventures.