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John Sheldon of SmileDirectClub: How To Create A Fantastic Retail Experience That Keeps Bringing Customers Back For More

An Interview With Orlando Zayas

Make it memorable. From our line of category-disrupting oral care products available in thousands of retail stores nationwide to our own SmileShops, making a statement that leaves a lasting imprint on your customers is important. Retail can serve as another means to grow your brand awareness. That’s why carrying through our iconic blurple branding was essential for building brand awareness at retailers like Walmart and CVS — it’s like 6-feet of an in-store billboard trafficked by millions every day.

As part of my series about the “How To Create A Fantastic Retail Experience That Keeps Bringing Customers Back For More”, I had the pleasure of interviewing John Sheldon, Chief Marketing Officer at SmileDirectClub.

In this role, he focuses on delivering the best possible experience to customers in order to continue growing SmileDirectClub and reach more people searching for affordable access to a straighter and more confident smile. As the Chief Marketing Officer, John oversees all digital media, paid media, creative development, social media, communication tactics, and experiential initiatives for the brand. As a results-driven marketing leader, John continually builds a track-record of success and is a champion for creating strategic plans based on key insights.

John has a strong background in digital transformation and innovation across a range of industries. He previously served as Chief Revenue Officer of Fresh Direct, a food tech company and the Northeast’s leading online fresh food grocer. He was also the Senior Vice President of Innovation Portfolios for Mastercard driving innovation globally for the company, and the Head of Strategy at eBay Enterprises Marketing Solutions. He has launched and worked with dozens of digital-first brands and lead the strategy to bring many great brands into the digital ecosystem.

John earned a B.S. in Economics with a concentration in Finance from the Wharton School of the University of Pennsylvania.

Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

I started my career in investment and securities consulting, but I quickly fell in love with e-commerce and digital marketing. Throughout my career, the roles, brands and industries I’ve worked in are vastly different, but they form a pattern. I bring an existing skillset, build a new capability, and then learn something along the way that dovetails nicely into my next chapter. I have always been drawn to roles that allow me to problem-solve and create a framework for the solution. Disruptive businesses are a great home for those like me who are motivated by creating something new. I love digging into customer data for insights just as much as dreaming up pie-in-the-sky ideas that generate irrational brand love. I get to do both at SmileDirectClub.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘takeaways’ you learned from that?

Back when the Internet was made of wood, I took a role at a consulting company that was focused on CRM. We set my title as “E-commerce Evangelist” when I came through the door. Interestingly enough, my presence alone unlocked the imagination within that company to explore the early days of e-commerce, before I really accomplished anything there. We quickly changed my title to focus on strategy. The takeaway I learned was that as a leader, you have to make sure that the team knows they have permission to think outside of their lane.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

I have been really fortunate to have two people teach me grit and resilience — skills that have benefitted me greatly in my career. For a person that is naturally impatient, these are crucial traits to develop. The first is Tobey Choate. He was my manager at the consulting company I mentioned before. I had never struggled to connect with a leader before, but our styles were very different, and I was banging my head against the wall. We were both the get-in-early types, and I used that time to try to communicate. For weeks, I would go into his office in the morning and basically sit there until he talked to me. He would ignore me. It took a long time, but I wore him down and he became an important mentor for me. There are still challenges for which he is my first call for help to think through. The second is Marc Fleishhacker, my leader at eBay. Honestly, his persistence is one of the true forces of nature. I would just observe his ability to stay with a problem like I was watching brain surgery. Enraptured.

Is there a particular book, podcast, or film that made a significant impact on you? Can you share a story or explain why it resonated with you so much?

Team of Teams by Stanley McChrystal is a favorite book and governs a lot about who I am as a leader. One of my favorite concepts from the book is “eyes on, hands off.” I would summarize it as, “If I can see what you are doing, what your queue of work is and how you are prioritizing, I don’t have to be up your shorts.” Make your work visible broadly.

What do you think makes your company stand out? Can you share a story?

SmileDirectClub has made teeth straightening — something only a small percent of the population could afford before — accessible to everyone. The transformation our Club Members experience from getting a smile they love is life changing, and their before and after photos speak for themselves. Sharing their stories is a key component of our marketing.

In a recent review, one of our customers said, “SmileDirectClub has literally changed my life!! I used to be self-conscious about my teeth for as long as I can remember. Growing up my parents couldn’t afford braces for me or my sisters. Nothing compares to how easy this is. Thank you SDC for my new confidence and new smile!!”

We’ve changed well over a million lives now, and we look forward to changing millions more.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

Find a job that inspires you at a company whose mission you’re passionate about. Every week we send a newsletter called “Inspired by Why” that showcases our customers’ incredible transformations. We send it so our Team Members can see the difference they are making in the lives of our customers and feel energized about our mission to increase access to premium oral care.

I’d also recommend you do something once a day that grounds you, and helps you focus on the most important things in life. For me, it’s a daily walk after work with my wife to decompress and talk about anything other than work.

Ok super. Now let’s jump to the main questions of our interview. The so-called “Retail Apocalypse” has been going on for about a decade. The Pandemic only made things much worse for retailers in general. While many retailers are struggling, some retailers, like Lululemon, Kroger, and Costco are quite profitable. Can you share a few lessons that other retailers can learn from the success of profitable retailers?

Agile omnichannel retailers who invested heavily into digital and e-commerce fared relatively well throughout the pandemic. SmileDirectClub is omnichannel, and we’ve found it beneficial to give our customers options and be wherever they want and need us to be. We offer three ways for our customers to get started: doctor-prescribed remote impression kits, or a visit to one of our SmileShops or Partner Network locations. When the pandemic hit and stay-at-home mandates began, we had the ability to quickly flip our business from a vast majority of customers getting started in our SmileShops to nearly 100% using our impression kits from the comfort and safety of their homes — practically overnight. Additionally, ensuring you’re providing a great experience digitally continues to be important. We’ve introduced enhancements to our customers experience with our telehealth platform during the pandemic, adding features such as a video chat with our Dental Care team or an app that makes following your treatment plan that much easier. Business models with flexibility and agility adapt better during this ever-evolving, ongoing pandemic.

Amazon is going to exert pressure on all of retail for the foreseeable future. New Direct-To-Consumer companies based in China are emerging that offer prices that are much cheaper than US and European brands. What would you advise retail companies and eCommerce companies, for them to be successful in the face of such strong competition?

Focus on the customer experience. If you deliver a fantastic experience, your customers will become life-long advocates for your brand and provide the best marketing you could ever imagine. Approximately a quarter of our Club Members come to SmileDirectClub from referrals and we work every day to get that number to be even higher.

What are the most common mistakes you have seen CEOs & founders make when they start a retail business? What can be done to avoid those errors?

Often, I see them overestimating the size of their target or not really understanding who their customer is. When you think you are “for everybody” you don’t end up talking to your real audience in their language, nor do you create the experience they want. Look to data to drive your decision making and get a profile of your customer base.

This might be intuitive, but I think it’s helpful to specifically articulate it. In your words, can you share a few reasons why great customer service and a great customer experience is essential for success in business in general and for retail in particular?

Creating a great customer experience is essential because a bad experience can do serious damage to your brand. According to the White House Office of Consumer Affairs, dissatisfied customers typically tell nine to 15 other people about their experience; some tell 20 or more. Customer referrals are one of the most cost-efficient ways to acquire customers and grow your business, and you don’t grow your business with referrals by delivering a bad experience — it’s the inverse. And now, in a world of Facebook, Instagram, TikTok, Twitter and others, sometimes they tell millions. These brand reputational challenges are really critical to monitor and manage.

We have all had times either in a store, or online, when we’ve had a very poor experience as a customer or user. If the importance of a good customer experience is so intuitive, and apparent, where is the disconnect? How is it that so many companies do not make this a priority?

I think companies can lose track of the customer and what the customer wants when they’re prioritizing growth, but keeping your focus on the customer is actually one of the best ways to grow and scale our business.

Can you share with us a story from your experience about a customer who was “Wowed” by the experience you provided?

Our Team was really moved by a video of young girl receiving a SmileDirectClub impression kit for the first time as a surprise from her mom. She had wanted to straighten her smile for so long that the sight of our well-branded impression kit brought her to tears. It shows how strongly your smile can impact your confidence, and that even the idea of beginning the SmileDirectClub smile journey brings our customers so much joy.

Did that Wow! experience have any long-term ripple effects? Can you share the story?

Yes — that young girl is Madelyn and we actually loved her story so much that we decided to turn it into a video and share it with the world. We know so many other teenagers — the largest segment in orthodontia — can relate to her story.

A fantastic retail experience isn’t just one specific thing. It can be a composite of many different subtle elements fused together. Can you help us break down and identify the different ingredients that come together to create a “fantastic retail experience”?

For me, it’s the combination of three things:

  1. A great discovery experience. Allow me to explore and learn about how to meet my needs.
  2. A great solution experience. Provide true clarity about why this product/solution is the best to meet my need.
  3. A great service experience. Make it easy for me to do business with you over and over again through informed, attentive, polite and fun experiences.

Ok super. Here is the main question of our interview. Based on your experience and success, what are the five most important things one should know in order to create a fantastic retail experience that keeps bringing customers back for more? Please share a story or an example for each.

  1. Make a great first impression. From the warm and friendly greeters to the cheerful blurple walls and Instagram-able “Smiles Made Here” signs, we want our customers to feel welcome and rest assured that their smiles are in good hands.
  2. Listen to your customers. We spend time with all our customers to get to know them and understand their motivation to straighten their teeth. We ask questions like, “How long have you been thinking about clear aligners?” or “If you could fast forward 6 months and have the new smile you’ve always wanted, how would you feel?” They’re motivated by a milestone like an upcoming wedding, a new baby, the start of a new career, or maybe their smile is something they’ve always felt self-conscious about and they want to make a life-changing transformation. Understanding why your customers are coming to you is essential to making a connection with your customer.
  3. Provide instant value. Customers don’t walk out of a SmileShop with their aligners because creating a highly customized, one-of-a-kind product takes a little time. However, that doesn’t mean our customers have to wait to start their journey to a smile they love. Our customers walk out the door with free whitening to begin to brighten their smiles that same day — keeping the excitement alive.
  4. Make it memorable. From our line of category-disrupting oral care products available in thousands of retail stores nationwide to our own SmileShops, making a statement that leaves a lasting imprint on your customers is important. Retail can serve as another means to grow your brand awareness. That’s why carrying through our iconic blurple branding was essential for building brand awareness at retailers like Walmart and CVS — it’s like 6-feet of an in-store billboard trafficked by millions every day.
  5. “Better is better.” This is one of our 7 Truths at SmileDiretClub. We believe in the spirit of continual improvement and are always improving the customer experience. Our leadership team holds weekly reviews of our SmileShop experience and provides feedback on what our highly trained Team Members do well and what they can improve.

Thank you for all of that. We are nearly done. Here is our final ‘meaty’ question. You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

I would move to bring back civility, particularly online. There is no discourse anymore. Anything said offends someone horribly with no benefit of the doubt given. People who hide behind anonymity online have successfully “shouted down,” cancelled or driven millions from engaging on topics they care about. No idea how to solve it.

How can our readers further follow your work?



This was very inspiring. Thank you so much for the time you spent with this!

About The Interviewer: Orlando Zayas is the CEO of Katapult, an award-winning omnichannel payment platform. Zayas is known for his revenue growth strategies and visionary leadership in the eCommerce and retail space. His future-forward expertise has led companies such as GE Capital, Safe-Guard Products International, and DRB Capital. Zayas is also highly committed to providing educational opportunities to underprivileged communities through his philanthropic endeavors. Zayas’ business insights are regularly featured in publications such as Forbes, Entrepreneur Magazine, Retail Insights, and more.




In-depth Interviews with Authorities in Business, Pop Culture, Wellness, Social Impact, and Tech. We use interviews to draw out stories that are both empowering and actionable.

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Orlando Zayas, CEO of Katapult

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CEO at Katapult

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