Ruben Harris

Ruben Harris is the Co-Founder and CEO of OutRival, creator of AI-powered Digital Workers that give every customer a dedicated assistant. OutRival makes it possible for brands to genuinely care about every single person they serve. It partners with them from first inquiry through every stage of the customer journey, with Digital Workers that remember every conversation, keep every promise, and bring in the right human at the moments that matter. OutRival started in higher education admissions and now serves schools, insurers, and travel brands across millions of conversations a month. Most partnerships begin with Warm Outbound calls, emails, texts, and voicemails that reach every inquiry within minutes. From there, OutRival maps the full customer journey with each partner and extends Digital Workers across onboarding, support, renewal, and re-engagement, so the relationship keeps growing long after the first conversation. As Ruben puts it, caring is the input, and performance is the output. Before OutRival, Ruben co-founded Career Karma, a Y Combinator-backed company that became the largest career transition platform in the country, helping hundreds of thousands of people reskill and break into tech careers. The company raised $52 million from investors including SoftBank, GV, Initialized Capital, and Kapor Capital. It is where the OutRival playbook was born: real call floors across three countries, proving that outreach at scale can still make every person feel known. Ruben also co-created the Breaking Into Startups podcast after a viral blog post about moving to Silicon Valley without a job and landing one in three weeks. The show reached more than 3 million people and built one of the largest communities focused on economic mobility. Today he hosts The New Normal (https://thenewnormal.fm/), where presidents, chancellors, and C-level executives share what it takes to genuinely serve every person who counts on them. Earlier, Ruben worked in investment banking, then joined mission-driven startups including Honor (elder care), Hustle (politics), and AltSchool (education). Originally from Atlanta, Ruben studied business and music. A classically trained cellist, he has performed at Carnegie Hall and landed placements with Def Jam. After nearly a decade in the Bay Area, he now lives in Miami, where he plays chess and develops real estate through Harris Towers, including TRINITY: https://www.liveattrinitymiami.com/