CEO of OutRival (YC W19)

Ruben Harris is the Co-Founder and CEO of OutRival, an AI company building digital workers, also known as conversational AI agents, for contact centers in high-touch, high-volume industries. While OutRival began by transforming admissions teams in higher education, its digital workers are now being deployed across healthcare, financial services, and other sectors where customer experience is critical and contact centers are essential. These AI agents integrate with enterprise systems like Salesforce, Epic, and PeopleSoft to streamline communication, accelerate outcomes, and reduce manual workloads across outbound and inbound channels like phone, text, email, and voicemail. Before OutRival, Ruben co-founded Career Karma, a Y Combinator-backed platform that helped hundreds of thousands of people reskill and break into tech careers. Under his leadership, the company raised $52 million from investors including SoftBank, GV, Initialized Capital, and Kapor Capital. Ruben also co-created the Breaking Into Startups podcast after writing a viral blog post about moving to Silicon Valley without a job and landing one within three weeks. The podcast reached over 3 million people and built one of the largest online communities focused on economic mobility and career transitions. Earlier in his career, Ruben worked in investment banking, then joined mission-driven startups like Honor (elder care), Hustle (civic engagement), and AltSchool (education) where he focused on partnerships and business development, collaborating with academics, union leaders, and political organizers on systems-level change in healthcare, outreach, and personalized learning. Originally from Atlanta, Ruben got his start organizing hackathons and nonprofit events while studying business and music. A classically trained cellist, he has performed at Carnegie Hall, taught music, and even landed placements with Def Jam. After spending nearly a decade in the Bay Area, he now lives and works in Miami with the OutRival team. He’s an active member of the NAACP, a chess enthusiast, and a frequent speaker on the future of work, education, and AI. Myers-Briggs: ENTJ