Jessica Strickland

Jessica Strickland is the founder and CEO of Matchmaker AI, an AI-powered concierge matchmaking platform based in Austin, Texas. With three years of professional matchmaking experience and nearly two decades in corporate leadership before that, she blends data, psychology, and old-fashioned human intuition to help people find real compatibility. Jessica is deeply versed in the frameworks behind lasting relationships, from attachment theory and conflict styles to personality systems like the Enneagram and Myers-Briggs, and she draws on real intake data from hundreds of singles to spot the patterns most people miss. She speaks candidly about the modern dating landscape, including the structural supply and demand imbalances reshaping how people meet, the limits of swipe-based apps, and wha...