Episode 39 : Jonathan Clarkson (CPO, Southwest Airlines) | Loyalty isn’t earned, it’s experienced

Today on the show we have Jonathan Clarkson, Vice President and Chief Product Officer at Southwest Airlines, where he has led the charge of building products and building loyalty experiences that help the airline win more customers and drive growth. His marketing foundation was shaped by iconic brands like Dr Pepper, Pizza Hut, and PepsiCo, giving him a sharp lens on how brands earn both attention and trust.And outside of work, you might find him running a race, exploring Napa or New York, or cheering on his Mustang at SMU.In this episode, Jonathan and I will dive into how experiences, AI, and smart product design work together to create lasting customer loyalty—with real examples of what loyalty looks like at Southwest Airlines and what it means for today’s consumers.Key Takeways from my conversation with Jonathan today:Loyalty is felt, not earned"It’s the little wins—smooth check-ins, fun touches, thoughtful surprises—that make customers keep coming back- not just rewards or points—but for the experience"Smart tech, personal touch"Use AI to simplify complex tasks and deliver tailored experiences, but combining that technology with empathy to keep the human connection aliveProducts level up logically" Build products with benefits that make sense step by step. Each upgrade should feel obvious and worth it—step by step, customers see why moving up makes sense.