The inside story: How CardFlight grew from 0 to 65,000 small-business customers in all 50 US states in 6 years

CardFlight CEO shares the story behind the company before CardFlight for the first time.
Derek Webster
Founder & CEO
Aug 12, 2020

Let’s start with a little-known fact about CardFlight. The company you know today as the brains behind SwipeSimple started out as a very different idea.

When I left the world of management consulting and my job at Oliver Wyman in 2011 and embarked on a new entrepreneurial chapter of my professional life, I initially had my sights on the consumer loyalty market and bringing the marketing power of rewards programs to small, local businesses. So I started LocalBonus, which allowed consumers to earn cash-back rewards from local merchants using their existing credit and debit cards.

Here’s what the LocalBonus homepage was, circa 2013:

LocalBonus raised over a million dollars of venture capital, signed up 800 partner small businesses, and even got written about in TechCrunch a few times. 

We learned a lot as we hustled to sign up new merchants and onboarded them for the program. Trying to establish a base of engaged consumers and participating small businesses - and getting the consumers to purchase more from small businesses in our network - was a complicated juggle and struggle.  The more we got to know the ins and outs of small businesses, the more we realized that there was another pain point besides customer loyalty, and a bigger area of opportunity out there.

CardFlight was born.

Or at least, that’s the “pretty” version of the story. 

The reality is that it’s a grind. It’s never comfortable to quickly change strategies and ditch what’s not working. The reason CardFlight has been successful is because we’ve powered through those setbacks and challenges — to maintain the tenacity and discipline to execute no matter what challenges were in our way, while also being nimble and responsive to the needs of our customers. 

Even CardFlight didn’t start out as the company and SwipeSimple product suite you know today. Our first product was the CardFlight Software Development Kit (SDK), which clients like Indochino, Peloton, and Reformation used to easily accept “card present” payments in their custom mobile apps.

Here’s a screenshot of an early CardFlight homepage, before SwipeSimple even existed:

For the record: we sold and supported the CardFlight SDK since 2014, but have not taken on new integrations in the past couple of years. 

Now SwipeSimple is our primary focus and source of revenue. We’re incredibly proud of the robust solutions we’ve built for small businesses on the go, in their store, and at their computer. 

This past week, we made the Inc. 5000 list of fastest-growing companies for the third time in a row. Few companies make the list two times, and even fewer make it three times. 

CardFlight was recognized on the Inc. 5000 list of fastest-growing companies in 2018, 2019, and 2020. Since the list measures growth over a 3-year period, that means we’ve made the list every time we’ve been able to qualify for it. Our first paying customers were onboarded in 2014. The 2018 Inc. 5000 list, the first year for which we ranked, measured growth from 2014 to 2017.

The versatility of our cloud-based solution and the focused execution it took to build it ended up being invaluable for small businesses around the country this year, as they adapted to social distancing guidelines to keep their customers and employees safe. A global pandemic certainly wasn’t something we anticipated or planned for — but it’s both gratifying and humbling that the versatility we built into SwipeSimple is able to help small businesses adapt and recover from this unprecedented event.

As I look back on the past several years, I’m grateful to our team, all the small businesses that use our easy-to-use software solutions, and the merchant acquirer and ISO channel that serves them.

Now I’ll leave you with thoughts of two of our very early hires.

First, from Paul Tower, Sr. Director, Application Development:

I’ve been here since we were just starting out. The past seven years here have been an incredible journey to be a part of as we built out our team, launched—and then kept updating and improving!—SwipeSimple, and brought our technology to over sixty thousand merchants and counting. I’m grateful to have been able to contribute to building CardFlight into what it is today, and I look forward to many more years of helping to develop safe and simple to use payments technology for small business merchants.

And here’s Natalia Leonardis, VP of Business Development:

This accomplishment is yet another sign of CardFlight’s sustained, stellar growth since inception—a feat that wouldn’t have been possible without our amazing partners. We're firm believers in the value of our dynamic channel and are grateful to our partners at leading merchant acquirers and independent sales organizations – including ten of the top thirty U.S. merchant acquirers – who have collaborated with us to bring our innovative, reliable solutions to merchants everywhere. As the payments industry continues to adapt to reflect today’s consumer needs and changing technology, we’ll be there every step of the way to help our partners and their customers access the tools they need to build and grow small businesses nationwide.

Thanks for your attention and support over the years. To learn more about the Inc. 5000 award, read the press release.