#148 From Engineer To COO: Catherine Wong On Leading With Empathy And Scale

What if the fastest way to grow your career isn’t a straight climb but a series of smart, sideways moves that sharpen your empathy and judgment?  In this episode, I had the pleasure of sitting down with Catherine Wong, COO and CPO at Entrata, to unpack how she scales products and people by shaping cultures where every voice is invited, and the best ideas surface early. From engineering during the dot-com downturn to leading global teams through acquisitions and hypergrowth, Catherine shares the habits that turn uncertainty into momentum: practice your voice, ask for real feedback, and reward behaviors that build trust.

We go deep on how product and operations intersect when you’re building an operating system for real estate. Catherine explains why diverse perspectives improve outcomes and how leaders can intentionally signal what matters by recognizing thoughtful execution, not just loud opinions. Her take on the future of work is refreshingly actionable: AI changes the “how,” not the “why.” Whether you specialize or stay broad, treat curiosity like a muscle. Run small experiments, unlearn out-of-date tactics, and stay anchored to clear business outcomes.

You’ll hear practical frameworks for deciding under ambiguity. widen inputs, seek data, welcome dissent, and iterate with agility. Catherine also breaks down visibility tactics for women who are competent but overlooked: volunteer for updates, lead slices of complex projects, and request precise post-meeting feedback. Her story of integrating a UK acquisition while battling imposter syndrome reveals a simple truth: courage plus clarity compounds into trust, scope, and impact.

If you care about culture design, product leadership, AI fluency, and building a resilient career in tech, this conversation is a blueprint you can use today. Follow along, share it with a friend who needs a nudge, and subscribe to get more candid, practical conversations. Loved this one? Leave a review and tell us the bold step you’re taking next.

Resources:
Catherine Wong on LinkedIn
Entrata

Chapters

• 0:00 Welcome And Guest Introduction
• 0:33 Defining Product And Operations Leadership
• 3:16 Career Origins And Early Lessons
• 7:11 Embracing Difference As An Advantage
• 10:06 Cross-Discipline Empathy And Lateral Moves
• 13:02 Designing High-Trust Team Cultures
• 15:24 AI, Skills, And Future-Proof Careers
• 18:05 Finding Your Voice And Getting Feedback
• 20:45 Deciding With Ambiguity And Agility
• 22:44 Mentors, Sponsors, And Continuous Learning
• 24:23 Stretch Moments And Imposter Syndrome
• 26:45 What Lights Catherine Up At Work
• 27:41 To Be Bolder: Final Reflections
• 29:15 Closing And Listener CTA