Cassandra Toroian
CEO Co-Founder in Delaware and South Florida
Cassandra Toroian, CEO & Co-Founder, Ruley the E-Referee | Co-Founder, Volleybird | Sports Tech Pioneer
A serial entrepreneur with 25+ years of building successful companies, Cassandra Toroian is revolutionizing amateur sports through artificial intelligence. As CEO of Ruley the E-Referee—recently named a finalist in the prestigious 2025 SFIA & Players Impact Start-Up Challenge—she's solving one of sports' most persistent problems: rule confusion that disrupts gameplay and discourages participation.
Ruley's AI-powered platform already serves five sports (tennis, pickleball, padel, golf, and soccer), delivering instant, accurate rule clarification to millions of players, coaches, and parents. Launched in February 2025, the ecosystem has rapidly expanded across iOS and Android platforms, with its proprietary API positioning the company to partner with sports federations, media companies, and global brands seeking to enhance fan engagement and player retention.
In parallel, Cassandra co-founded Volleybird (March 2025), an innovative subscription commerce platform curating premium gear for sports enthusiasts—further demonstrating her ability to identify and capture emerging market opportunities.
Her transition from finance to technology showcases remarkable adaptability: after successfully exiting previous ventures, she completed an intensive Python coding bootcamp at the University of Miami, adding technical expertise to her MBA in Finance and deep understanding of business strategy. This unique combination of business acumen and technical knowledge drives her mission to democratize information and make sports more accessible worldwide.
A sought-after voice on innovation and entrepreneurship, Cassandra has shared insights on CNBC, Bloomberg Television, Fox Business, and in The Wall Street Journal. She authored "Don't Buy the Bull" (2010), with her second book on entrepreneurship and technology forthcoming in 2026.
Drawing from her experience as a Division I tennis player at Lafayette College, Cassandra understands firsthand how sports build character and community. This passion fuels Ruley's core mission: eliminating disputes so players can focus on what matters—the joy of competition, personal growth, and bringing people together through sport.
"Technology should enhance human experiences, not complicate them," says Toroian. "Every disputed call is a missed opportunity for connection. We're building the infrastructure for fairer, more enjoyable sports at every level."