Cassindy Chao is a third-generation matchmaker, former Goldman Sachs and JP Morgan Securities investment banker, and tech executive turned premier relationship expert. With a deep understanding of both human connections and high-stakes finance, she blends tradition with modern insights to help professionals find lasting love.
Her matchmaking journey started early—at Wellesley College, she orchestrated a wildly successful mixer for over 100 students, setting the stage for her career. Today, Cassindy is recognized as the top matchmaker for Asian professionals, working with high-achieving clients, including CEOs, doctors, and artists, to navigate the complexities of modern dating.

Beyond matchmaking, Cassindy is the author of Ancient Wisdom, Modern Love: Chinese Wisdom for Dating Success, where she combines Eastern philosophy with practical dating advice. A sought-after speaker, she has delivered sold-out talks at venues like the Harvard Club of New York, or the Museum of Chinese in America, captivating audiences with her insights on love, relationships, and personal branding. She is frequently invited to speak on guiding ultra-high-net-worth families in discussions about dating and marriage, as well as navigating modern relationships with a cultural lens.

Deeply committed to her community, Cassindy serves as Co-President of the Wellesley College Asian Alumnae Alliance, a Development Committee member for Asian Health Services, and an Associate Board Member for the New York Asian Film Festival.
When she’s not matchmaking, speaking, or writing, you might find her playing a fierce game of mahjong (yes, she’s also a mahjong teacher!), making homemade Taiwanese foods, or planning her next adventure—always with great relationships in mind.