
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
careerkarma.com
suntrustrh.com
breakingintostartups.com
bmo.com
hustle.com
honorcare.com
altschool.com
Miami, Florida, United States
CEO
OutRival
• www.linkedin.com/company/outrivalai
Oct 2024 - Present
Miami, Florida, United States
CEO
Career Karma
• www.linkedin.com/company/career-karma-app
Apr 2018 - Present
San Francisco Bay Area
Co-Host
Breaking Into Startups
• www.linkedin.com/company/breaking-into-startups
Dec 2016 - Present
San Francisco Bay Area
Special Advisor
Hustle
• www.linkedin.com/company/hustle-texting
Apr 2017 - Jul 2018
San Francisco Bay Area
Director of Sales
Hustle
• www.linkedin.com/company/hustle-texting
Aug 2017 - Feb 2018
San Francisco Bay Area
Partnerships & Lead Generation
Honor
• www.linkedin.com/company/joinhonor
Sep 2015 - Apr 2017
San Francisco Bay Area
Advisor
AltSchool
• www.linkedin.com/company/altschool
Aug 2015 - Jan 2016
San Francisco Bay Area
Investment Banking Intern
Brookwood Hill Group, Inc.
Jun 2010 - Sep 2010
Atlanta, GA
Financial Analyst Intern, Acquisitions
Regency Senior Living (Mountain View Retirement, LLC)
May 2010 - Aug 2010
Collegedale, TN
Marketing Manager
WoodLake Entertainment
Sep 2007 - May 2010
Greater Atlanta Area