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

Good product people do not necessarily come from the customer service gene pool. Like any company, you need a kick ass product team married to a kick ass sales, marketing and support team — unfortunately, that is much harder than one thinks.

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 Jon Squire, Co-Founder & CEO of CardFree.

Jon Squire has more than 20 years of business, marketing and product development experience in financial services and emerging technologies. Jon founded CardFree in 2012 with the vision of filling a gap in the marketplace for an integrated commerce platform for large merchants. Prior to CardFree, Jon served as CMO at CorFire, SK C&C’s global mCommerce division, where he managed sales, business development, strategy and marketing. Jon was also SVP of Mobile Payments at mFoundry where he helped create the first mobile wallet initiatives in the U.S. with retailers, carriers and financial institutions. Between his work at CorFire and mFoundry, Jon has been involved in the two largest mobile payments programs in the nation.

Jon has consistently driven innovation and created world-class product offerings in new categories. He launched the first national mobile P2P offering in partnership with Sprint and PayPal and is well known for his leading-edge work with NFC, barcode and alternative technologies that integrate with the point of sale. Earlier in his career, he also led mobile/e-commerce payment initiatives for Wells Fargo and ran E*TRADE Advisory Services.

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’ve been chasing the mobile payments/commerce space for the better part of 20 years, with a breakthrough a handful of years in, with the Starbucks mobile application. It highlighted those restaurants, and hospitality in general, hold the keys to changing consumer behavior. Over 2 billion transactions and countless pounds later, CardFree provides end-to-end payment, ordering and loyalty services to some of the best brands in the world.

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?

Always make sure you have Wi-Fi coverage! In our first few weeks of announcing CardFree, we were invited late into an RFP for a top 5 restaurant brand. We would only have two weeks to pull off a full end-to-end demo of our ordering platform because everyone else had already been through the six-month process. We eagerly accepted the challenge, and the next two weeks involved a lot of sleepless nights. Come the morning of the demo, no one had slept, pulling an all-nighter to assure we could fire the order into the point of sale. We knew there would be a committee involved in the selection but did not anticipate walking into a room of 75+ people. The meeting was to begin promptly at 8 am, and during the pregame setup, we casually asked what the Wi-Fi network/password was to get online. We were then told that given this room was in the basement of the building, Wi-Fi never worked. Sweat began to form on all our foreheads as our CTO did a fantastic tap dance to buy us time. We ran upstairs and googled the nearest store for a hotspot, but it didn’t open for 30 mins — one of our fearless team members went anyway (what choice did we have?). Upon getting to the store, he began wailing on the window and begging the manager to let him in…he did, we did, and the rest is history. Later, we found out we were the only company to get the order to process successfully!

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?

The demo story highlights that it’s never one person, definitely not the CEO, who forges your success, but rather the team behind you that collectively gets you over the line. We are where we are today largely due to the entire squad pulling as one.

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?

I remember loving Atlas Shrugged as a teen. For me, the concept of success and driving for the best product one can produce largely were born from those pages. Then again, I also loved Jaws, particularly the scene of Hooper, Chief and Quint comparing scars — that kind of bonding makes for unique teams.

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

A rare combination of being built for scale with a foundation of listening to our customers first. We took on a lot of industries by cutting across payments, ordering and loyalty — and in the early days our competitors said we would never be able to build a platform that broad. Listening to what our partners needed and committing to build it at the largest of scales, allowed us to work with amazing brands like Dunkin’, Taco Bell, Sonic, etc. Now our competitors who were pure plays in ordering, payment and/or loyalty are all trying to bolt on components to their architecture.

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

Laugh and balance. In the early days, when my kids still wanted me around, coaching was the perfect escape — you need an activity that forces you to focus 100% on something non-work related. These days being on the water has the same effect.

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?

Nobody expected Amazon and nobody expected a pandemic in our lifetime (apparently other than Bill Gates:), both highlighted a need to ‘be better than the Gap’ and be nimble at the same time. What I mean by that is the brands we empower have embraced the notion that the experience is the differentiator, and that experience has fundamentally changed. Today’s consumer wants their product how they want it or they will just go online, or down the street, and get it from someone else. Torchy’s launched premade drinks and taco trucks (back to their roots) during the pandemic…Dunkin’, already strong in drive thru, pushed folks to leverage the app and stay in their cars driving enormous sales in the drive thru channel…our hotel partners implemented mobile ordering and saw orders jump by 60%…and a ton of our restaurant partners launched Text-to-Pay, Pay@Table and Order@Table to allow the customer to drive their own experience and minimize contact, both driving sales and augmenting staffing shortages.

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?

In an era rife with competitive pricing from retail giants like Amazon, brands looking to win customers (and keep them coming back) must offer a better, more unique and convenient brand experience. It doesn’t just stop there with creating a frictionless customer experience; brands also must create a level of emotional connection between them and their customer and offer value beyond the product itself.

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?

Universally, a fear that technology will lessen their relationship with their customers. One of the great things that has come out of the last few brutal years, is that technology proved it can bridge the gap between the anonymous customer while also driving sales in the toughest of environments. Take the time to evaluate your roadmap and don’t just hire the one-off solution to get your board off your back!

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?

There are just too many choices these days to not be the best — or at least making the customer feel like you’re trying to be the best. If you’re a market that carries a specific hot sauce that I love, but charge 10% more than Amazon does, will I continue to buy it from you -especially if I can get it delivered for free the next day? Only if the market provides other unique benefits like service and products that are hard to replicate. It is without a doubt the most demanding customer base since Veruka Salt, and most retailers aren’t lucky enough to have Oompa Loompa’s.

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?

Good product people do not necessarily come from the customer service gene pool. Like any company, you need a kick ass product team married to a kick ass sales, marketing and support team — unfortunately, that is much harder than one thinks.

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

We’ve got a casual dining partner who recognized our agility on the payments side or the house and casually asked us on our weekly call if we’d ever consider getting into tableside EMV transactions with a terminal. As our name is CardFREE, the jokes became weekly as we mulled it over and looked into the space. More than a handful of people told the same Head of Technology that challenged us to come up with a solution that we could never pull off. Six months later we are in market with a best of class solution that has more features that anyone in the space and the Head of Technology was elated — we killed two birds with one stone, allowing him to leverage one vendor for multiple payment experience (e.g., Pay@Table, Text-to-Pay and EMV) and building a solution that didn’t exist in the market.

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

Time will tell :), but I’d love to think we got a partner for life.

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”? 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.

The five most important aspects to be mindful of are:

Convenience: People are busier than ever and adding to the clicks, calls, stops, payments, etc. they have to do in a given day will only get you dropped from their go-to list. Dunkin’s brand is built around ‘Runnin on Dunkin’ so embracing the natural speed that comes with ordering ahead and skipping the line was a no-brainer for both the brand and the customer. People don’t go to Dunkin’ to lounge and read the paper, they go to get their fuel for the morning and work. Embracing tech that made that easier was a win win.

Frictionless: Similarly adding friction to any part of a customer’s day is never a good idea. When Starbuck’s broke the mold and launched mobile payments, they were hell bent on not slowing the line and not making the customer do more than they would do in a physical card world. A defining moment was when people realized they could reload their gift card standing in line — before they got to the counter — and not be that person who pulls out a checkbook at the grocery store accompanied by groans. Reducing friction increased line speed and drove more sales.

Unique: A lot of the brands we work with are successful because they have unique identities and realize that combining that identity with tailored technology can be a win. TreeHouse Brewing drove massive adoption of mobile ordering by leveraging great training and greeting folks personally by their vehicles during COVID and walking them through the new contactless journey.

Scalability: The last thing you want to do is crush it with a new product only to realize you can’t support the sales and demand. In our early days one of our partners had a novel idea of giving away a free product for bases stolen in the playoffs — this was a first ever on a national level. They also warned us a few days prior that this would be fulfilled via our mobile platform…. luckily, we’d built a network that was focused on the largest of scale (not to say we didn’t melt a few server farms during). Partner with folks who can help you scale, and sleep at night.

Data Mining: Partner with folks that will make your data work for you vs. them using it for their own goals. Your data drives and informs loyalty, repeat business and things like smart pairings. A lot of our partners will look at daypart, food preferences and things like weather to deploy informed marketing strategies — driving both new sales and larger basket.

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. :-)

There is plenty we need to fix right now, but I will stay with climate change for this one. It’s become clear with all the divisiveness in the political/public forum there won’t be any significant change any time soon. I would propose that the private sector try to step in — how about neutral 3rd parties accessing a given companies carbon footprint and then the company sets up a matching funds program similar to 401k’s, that is accessed annually and tax deductible. Employees can also participate in this and also reduce their tax burden. The company can pick from a handful of ways to apply the funds to help fight climate change.

How can our readers further follow your work?

Just visit us at CardFree.com or look for ‘powered by’ at your next great hospitality experience.

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