2025 Winner

Anupama Vaid

Founder & President, ParentSquare

The Entrepreneur Improving Student Outcomes One Message at a Time

A former software company team lead, Anupama Vaid climbed the corporate ranks by excelling at communication. But despite her years of professional experience, as a parent, she often found herself struggling to effectively communicate with her children’s teachers. Enter ParentSquare, which Vaid founded in 2011 to provide accessible digital tools that make it easier for families to engage with their kids’ schools, a research-backed predictor of student success. The last few years have marked a period of aggressive expansion for the company — in 2024, ParentSquare made Inc.’s list of the top 5000 fastest-growing companies, thanks to its whopping 637% three-year revenue growth. Today, the platform serves 20 million students across roughly 4,435 districts helping close the communication gap between home and classroom — one message at a time.

By Laura Entis