Meet the CEO Helping Enterprises Turn Cold Pipelines Into Revenue
Ruben Harris is not waiting for the future to arrive. He’s already running it.
The CEO and Co-Founder of OutRival — a YC-backed AI company supported by Initialized Capital, Google Ventures, and SoftBank — Ruben is building the infrastructure behind a new class of enterprise worker: Digital Workers that don’t wait to be contacted. They reach out. They re-engage lapsed students, revive cold pipeline, warm insurance leads, and close the gap between opportunity and revenue through real voice, text, and email conversations at scale.
It’s a category higher education, insurance, and travel have long underestimated. OutRival is making that the competitive advantage.
His path here wasn’t linear — it was layered. Investment banking. Three startups spanning education, healthcare, and politics. The co-founding of Career Karma, a platform built to open doors for people who didn’t have the map. Each chapter added a dimension: financial fluency, sector depth, a founder’s instinct for where the market hasn’t caught up to the problem.
As an emerging developer with his company, Harris Towers, Ruben is helping to address a gap Miami residents know well but rarely see solved. TRINITY — the portfolio’s flagship development, brought to life through CO2 Homes in partnership with Borges Architects, 64North, Cetoute Design Group, and Kobi Karp — is a curated collection of three modern residences situated at the edge of Buena Vista and Little Haiti. Each home spans more than 3,000 square feet across multiple levels, with private elevators, rooftop hot tubs and cold plunges, and floorplans designed to balance connection with privacy.
The concept draws from lived experience. Ruben and his partners have lived in intentional co-living environments alongside founders of Asana, the Facebook Like Button, and Google Maps — spaces where proximity to the right people accelerated everything. Trinity is that same spirit, reimagined for Miami: homes that function equally as startup headquarters, creative studios, multi-generational residences, or simply a life lived with more intention, in the heart of the city rather than away from it.
For those who wanted more than a condo but less than a waterfront compound — and who refused to leave Wynwood, Midtown, or Brickell to get it — TRINITY is the answer.
And somewhere in between, Carnegie Hall. Ruben is a classically trained cellist — a detail that is less a footnote and more a frame. Precision. Timing. The discipline to master something difficult because the work demands it.
That’s the through-line.
Congratulations to a legacy builder operating at full range.
Learn more at https://www.outrival.com/
