Meet an Enrich Member: Rodrigo Oliveira
Today we’re chatting with Rodrigo Oliveira, the CTO at Glassdoor. We love how Rodrigo describes himself — “I’m passionate about using technology to empower people—whether through jobs, health, or personal growth.”
Tell us a little bit about yourself:
I’m Rodrigo Oliveira, a tech executive, entrepreneur, and software engineering leader. I currently lead engineering, data, and ML at Glassdoor as CTO, where I’m focused on reimagining career discovery through AI. I’ve previously co-founded a fitness app acquired by WW, where I then served as CTO.
What was your first job? What did you learn there?
My first job was as a soccer coach for under-10 girls (while in college). It taught me the foundations of leadership: how to motivate different personalities, simplify complex ideas, and build a team culture that balances learning with fun. I also learned the importance of meeting people where they are, whether it’s a kid struggling with coordination or an engineer ramping up on a new system, progress starts with empathy and clear communication.
What’s something you’ve changed your mind about recently?
I used to think that AI-generated code would only help with boilerplate. But now I know it can meaningfully accelerate architectural thinking and strategic design when paired with a thoughtful prompt or toolchain.
What’s something you want to get better at this year?
I want to deepen my ability to apply AI, from rapid prototyping to designing agentic systems that solve real problems. At the same time, I’m increasingly curious about the edges: where AI enhances human connection versus where it falls short. I want to explore how we can use AI to support more meaningful, human-centered experiences—especially in areas where authenticity, empathy, and trust can’t be fully automated.
What books are on your bedside table or Kindle?
I tend to gravitate toward books that explore the human condition, systems of power, and long arcs of progress. Favorites include Sapiens by Yuval Noah Harari, 1984 by George Orwell, and Pillars of the Earth by Ken Follett. I like books that zoom out to show how we got here—or zoom in to show what people endure and build through time.
Who is your dream Enrich member?
Someone from Duolingo. I really admire how they rode the mobile wave to build an addictive, mission-driven product—and how they’re now leaning into the AI wave with the same creativity and discipline. I’d love to connect with someone who helped shape that trajectory, especially around product, growth, or applied AI.
