Ben Segal’s career has two chapters. The first was in sports and entertainment venues— spending time with the Yankees, Mets, Patriots, Bruins, Madison Square Garden, Barclays Center, and others. Then, he moved into DTC e-commerce. He worked with Freshly, Pair Eyewear, and Thesis. For the past year and a half, he has taken a spin at consulting for over 20 brands. This allowed him to use nearly every tool in the CX tech stack and gain a broader perspective. 

 

Let’s see what he’s learned from working with so many brands big and small that can help you lead yours.


This interview has been edited for clarity.

Gabe: Your career has had an interesting shift—from going deep with one company to getting this broad view across many. Has most of the consulting been in DTC?

Ben: At first, yes. I was with CreateCX, focusing on DTC e-commerce. Now, with The CX Audit, I'm getting back to my roots in in-person experiences—dining, movie theaters, museums, restaurants. These businesses have digital presences, but I'm really interested in improving hospitality and the onsite customer experience.

Gabe: What’s the biggest difference between the in-person world and digital CX? Or is there more overlap than people think?

Ben: Funny enough, I wrote a book about this. I actually think there’s a lot more in common than people assume. In person, you're creating an experience for one individual in real time. In e-commerce, it feels like you're serving millions, but really—each person is alone, on their phone or computer. So it’s still about that one individual. If you can make the experience right for one person at scale, that’s where the magic happens.

Gabe: Interesting. Is there something the DTC world misses that in-person experiences get right?

Ben: Yeah, definitely. DTC brands often try to create personalization through automation—like pulling in a customer’s first name for an email—but it can go sideways fast. We've all seen emails that say “Hello, F.NAME.” It comes off as robotic. In person, there’s more opportunity for genuine, human connection. And if you try to fake it digitally, it can backfire.

Gabe: Totally. I’ve seen so many of those bad personalization attempts. So, how do you find the balance between automation, personalization, and consistency?

Ben: Here’s the mantra I go back to: Automate the predictable, humanize the meaningful. Consistency can come from solid knowledge bases, macros, and process design, but that shouldn’t eliminate warmth. Tools like AI agent assist can help surface context so templated replies still feel personal. The goal is to be reliable without sounding robotic. That’s achievable with the right systems.

Gabe: That’s such a great line—automate the predictable, humanize the meaningful. I imagine that applies to AI, too?

Ben: Absolutely. AI can and should help, but it shouldn’t replace humans entirely. It’s best when it handles the repetitive tasks—stuff that wasn’t enjoyable for agents anyway—and frees them up for more meaningful interactions. I’ve seen human-in-the-loop approaches work well. Done right, the customer experience improves, not just in terms of cost, but in overall quality.

Gabe: Love that. On another note, I spoke to a CX leader recently who said they’re juggling so much, they don’t even know where the real problems are. Have you seen any common warning signs that signal potential issues with customer loyalty?

Ben: Yes, that’s a big focus in my consulting work. Most brands either aren’t tracking early warning signs, or they’re looking at them the wrong way—purely based on ticket volume.

What I recommend is overlaying what customers say with what they do. For example, 20–25% of support tickets might be about “Where’s my order?”—but those customers usually come back and buy again. They're eager for the product.

On the other hand, you might see only 4–5% of tickets about fit issues—glasses not sitting right, shirts not fitting well. That’s a small number, but those customers often don’t return. And they may tell others the product didn’t work. That’s a major churn risk.

So rather than just looking at ticket volume, I suggest tracking customer intent and behavior together to identify the issues that actually hurt loyalty, even if they show up less frequently.

Gabe: That’s so insightful. But that kind of data integration sounds hard—are most brands set up to do it?

Ben: It’s not easy. I’ve seen it done well, but only with custom-built solutions. Every brand has different tools and systems, so there’s no plug-and-play solution—yet. But if someone builds it, that’s going to be the tool everyone wants.

Gabe: Outside of AI, are there any other trends CX leaders should be watching to stay ahead?

Ben: Yes. Given the current economy, there’s more pressure to prove that CX isn’t just a cost center. I’m seeing a shift toward high-impact, low-budget strategies—like retention or win-back campaigns.

For example, using tools like Looker or ThoughtSpot to identify high-spending customers who haven’t purchased in a while. Then, your CX team—who now has more time thanks to AI—can reach out with a personal message. Something like, “Hey, we know you loved this product. It’s coming back.” That kind of proactive outreach can drive real revenue without increasing CAC. It's about showing CX as a revenue generator.

Gabe: That’s powerful, especially in this environment. As we wrap up, what’s one piece of advice you’d leave for CX leaders?

Ben: I know AI is overwhelming and noisy. It’s easy to throw up your hands. But now is the time to lean in. Take the demos. Ask the questions. Try the tools.

It reminds me of the early Internet days—when we were all figuring out AOL, Google, Yahoo, Ask Jeeves. Those who explored and played around understood the evolution better and were better prepared for the future. I think we’re in a similar moment now.

The people who dive into AI, who understand what each version does and how it's progressing, will be the most informed moving forward. So don’t check out. Get curious.

Gabe: Love that comparison. Feels like we’re right at the edge of something big. Whether you end up using a tool or not, there’s a lot to learn from just being in the conversation. Appreciate the time, Ben. You’re doing great work with The CX Audit and beyond—thanks for everything you’re contributing to the space.

Closing thoughts

Ben’s journey reminds us that unforgettable customer experiences start with human connection—whether in-person or online. For customer service leaders, the takeaway is clear: prioritize personalization, embrace AI where it adds value, and always keep your eye on what really drives loyalty. As the CX landscape evolves, those who stay curious, data-driven, and human at heart will lead the way. Now’s the time to lean in, experiment, and turn service into a serious growth engine.

Are you evaluating which CRM tools will help you get an edge over the competition? Check out our guide to help you know what to look for in a customer experience CRM platform.