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. Before that, I co-founded a fitness app that was acquired by WW, where I later served as CTO. Across all these roles, I’m driven by building products that meaningfully improve people’s lives.
What was your first job? What did you learn there?
My first job was as a soccer coach for under-10 girls while I was 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, clarity, and patience.
What’s something you’ve changed your mind about recently?
I used to think AI-generated code would mostly help with boilerplate. Now I see how—paired with thoughtful prompts and the right tooling—it can accelerate architectural thinking, illuminate alternative designs, and push strategy forward. It’s become a true creative partner rather than a convenience tool.
What’s something you want to get better at this year?
I want to deepen my ability to apply AI end-to-end, from rapid prototyping to designing agentic systems that solve real problems. I’m also increasingly curious about the edges: where AI genuinely enhances human connection versus where it still falls short. This year, I want to explore how to use AI to support more meaningful, human-centered experiences—especially in domains where authenticity, empathy, and trust still matter more than automation.
What books are on your bedside table or Kindle?
I gravitate toward books that explore the human condition, systems of power, and the long arcs of progress. Favorites include Sapiens by Yuval Noah Harari, 1984 by George Orwell, and The Pillars of the Earth by Ken Follett. I love books that zoom out to show how we got here—or zoom in to show what people endure and build over 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.
