January 27, 2025

#131 How American Express Consistently Reinvented Itself for the last 175 years w/ Ryan Cailliet—VP of Research and Design at American Express

45 minutes

More than ever, we expect more from our technology.

With self-driving cars from Tesla, AutoPay, and AutoSaving, as well as same-day shipments and grocery delivery, we expect our technology to think for us, not the other way around. Historically, large legacy companies have failed to make this a priority, thinking that traditional operational models and hand-holding SOPs are enough to retain the business of millennials and Gen-Z.

In this episode, we discuss how American Express has reinvented itself over the past two centuries. It started as a freight forwarding company and continued to innovate with traveler's checks, credit cards, and, eventually, a strong digital technology experience. Ryan joined American Express in its next iteration of doubling down on its mobile app experience, modernizing its credit card application offering to utilize all the data available to eliminate the misleading “pre-qualification—all to cater to the new rising market of Gen Z through their “Apply with Confidence” Product.

Actionable Takeaways

✅ Redefining Product Management

"My job is not to be right. My job is to get it right…and a lot of the product managers (are) so focused on proving their value and how good they are that they can't afford to be wrong.

But the longer you go in your career, you find out that being right—out of the gate is probably the worst outcome that you can drive." - Ryan Calliet

Pro Tip: Many failed products were based on an influential individual trying to sound smart at the cost of doing the legwork required to find the right solution and get the execution right.

Even if Ryan is wrong, the first couple of attempts and the lessons learned in those failures usually give the insights needed to get it right the next time.

✅ Building Trust through Being Considerate in the Design Process

"Acquisition is your first experience with a brand. We want to make sure we get off on the right foot, build a trusting relationship and that you come back to us as you grow and evolve over time." - Ryan Calliet

Pro-Tip: Ryan's user-centered design fosters transparency and trust, essential for customer relationships amid skepticism. After months of effort, their pre-qualification experience failed because customers lacked trust in it, viewing it as not a guarantee of approval from Gen Z, new to the credit card market. The team refined their plans to ensure successful approval outcomes. This challenging process required collaboration with legal, compliance, and credit bureaus. Ultimately, it resulted in strong adoption among Gen Z.

✅ Taking Calculated Risks

"Risk-taking is a part of this job. You can't know how people will react to a product until it’s out there. (Counting on evidence) “Beyond a reasonable doubt” is great because you have to make that judgment." - Ryan Calliet

Pro-tip: Being data-driven 100% of the time isn't possible. Eventually, you have to make a judgment call. So, if you feel like you're at least 75 percent confident, which in the legal system is “beyond a reasonable doubt,” it's worth trying out the idea.

If you're less than 75% and closer to 50%—or less than 50%, maybe it's time to take the idea back to the drawing board and continue your research until you have more confidence in another direction.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.wayofproduct.com

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By Caden Damiano

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