How Chubbies is Building a Community of Advocates & Lifelong Customers

Gladly Team

Read Time

7 minute read

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Chubbies, the brand that’s all about building that Friday at 5pm feeling, is not only known for their bright colored, retro-style shorts, but more importantly, their close-knit community of advocates and loyal fans.

I had the pleasure of chatting with Tom Montgomery, Co-Founder and Chief Digital Officer of Chubbies, on Radically Personal, a podcast by Gladly where we talk to leaders of today’s most innovative brands about their approach to delivering radically personal customer service.

During my discussion with Tom, we talked about the power of building community amongst your customer base, how text message is becoming the channel of choice, and so much more.

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Building community doesn’t just entail selling products and services consumers like. It’s about focusing on the individual and going above and beyond during every interaction you have with them. At Chubbies, going above and beyond for their customers is the norm and those great experiences not only get shared publicly, but they turn a one-time customer into a customer for life.

“It’s one of the things that we’ve tried to embody in the way we approach customer service and customer experience, in general, is give people such positive experiences and such interestingly positive experiences that they become stories and they become conversations.”

Tom Montgomery

Co-Founder & Chief Digital Officer

Listen to this episode on Apple podcastsSpotify, or on the web at

In addition, in the era of instant-everything, it’s no surprise that text message is becoming an increasingly popular channel amongst most consumers, especially a younger demographic. Chubbies launched text message with Gladly last year and it’s proven to become the channel of choice for most customers—in fact, it’s making up about 1/3 of Chubbies contact volume and shows no signs of slowing down.

“… if you want live communication, there’s not a great experience outside of SMS because your chat experience is live, but you’re tied to a website. Your voice experience is live, but because it’s such an arduous channel for our team to handle…and email is inherently this latent lag channel because there’s so much structure to the conversation.”

Tom Montgomery

Co-Founder & Chief Digital Officer

And finally, what’s Radically Personal without getting radically personal? I was excited to learn that Chubbies is launching Foundation 43 later this year—a foundation aimed at supporting mental health. There are 43 muscles in your face, which are used to show—or sometimes hide—emotion, the way you’re feeling or the way you’re thinking. The foundation is partnering with other organizations that are on this pursuit of supporting ongoing mental health and well-being efforts. We are so excited to hear more about this incredible work later this year.

Tom, thanks again for being such a great partner and friend to Gladly and sharing the same passion for great service that we do.

Be sure to listen in to the full episode where we talk about all this and a whole lot more.

Listen to this episode on Apple podcastsSpotify, or on the web at


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