Sandbox to Scale: The Early Childhood Landscape with Playground's Sasha Reiss

How can AI, automation, and smarter business operations help childcare providers navigate rising costs, shrinking margins, and an increasingly challenging funding landscape?

I recently sat down with Sasha Reiss, Co-founder & CPO of Playground, in a special GSVtv Podcast to discuss the future of early childhood education, childcare management technology, and the business challenges facing preschool owners and operators.

Sasha shares the very personal origin story of Playground, an early childhood education software platform recently acquired by Procare Solutions, and how a simple app built for a family-owned preschool evolved into a solution designed to streamline childcare operations. We talk about how AI agents and automation can help providers manage enrollment, tuition collection, parent communication, administrative tasks, and marketing while giving educators more time to focus on children — plus the economic pressures reshaping the childcare industry, including changes in federal and state childcare subsidies, Head Start funding uncertainty, rising operating costs, declining enrollment, and the impact of universal Pre-K on private childcare providers. Sasha explains why operational efficiency, differentiated programming, and stronger enrollment strategies are becoming essential for sustainable childcare businesses.

Sasha also hares advice for early-stage EdTech founders on building products around real customer needs, understanding the complexities of education markets, and why sales, marketing, and change management are just as important as great technology.

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Stream the conversation now:

• YouTube: https://asugsvsummit.com/video/sandbox-to-scale-the-early-childhood-landscape-with-playgrounds-sasha-reiss-gsvtv-podcast
• Spotify: https://open.spotify.com/episode/3t6MWFvfxrKMHVs5fuzd2l?si=Sifl2tzNRWeQ6nmVFnAb-g
• Apple Podcasts: https://podcasts.apple.com/us/podcast/sandbox-to-scale-the-early-childhood-landscape/id1809279842?i=1000797827488