Bringing Modern EdTech to Underserved Schools with Robby Cobbs & Kyle Sumrow of Tech My School
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In this episode of Tech Can’t Save Us, Paul speaks with Robert Cobbs, CEO and founder of TechMySchool, and Kyle Sumrow, the organization's director of development
This week on Tech Can’t Save Us, host Paul David is joined by Robert "Robby" Cobbs, CEO and founder, and Kyle Sumrow, director of development at TechMySchool. As the Caribbean’s leading EdTech consulting nonprofit, TechMySchool serves over 40 schools across Puerto Rico, the U.S., and internationally, helping them modernize systems and create student-centered learning environments.
They discuss the fundamental disconnect in modern education, where schools often have more technology than ever but feel overwhelmed and underprepared to use it effectively. Robert and Kyle explain how educator hesitation and a "retreat from technology" driven by parental concerns about screen time are shaping the current landscape.
Key conversation points include:
- Individualized Tech Plans (ITPs): How TechMySchool uses a non-judgmental, data-driven approach to diagnose school needs across educational systems, adult learning capacity, and student empowerment.
- The "Flock Leader" Program: A sustainable model that pays stipends to teachers to step into leadership roles, ensuring schools build long-term internal savvy rather than relying on one-off workshops.
- The Puerto Rico Context: The unique challenges facing students in Puerto Rico, who often lack access to basic infrastructure like public libraries and enter the continental U.S. workforce several grade levels behind their peers.
- Leading Through Curiosity: Why the most successful school transformations happen when leadership prioritizes a growth mindset and models a love of learning for their students.
Robert and Kyle also share insights from their international careers—spanning from Saudi Arabia to Switzerland—and explain why their "terrible business model" of trying to work themselves out of a job is the most ethical way to support schools.
Find more about TechMySchool here: https://techmyschool.org
Robert Cobbs: https://www.linkedin.com/in/robertcobbs/
Kyle Sumrow: https://www.linkedin.com/in/kyle-sumrow-869516183/