Charlie Youakim
CEO / Sezzle
By Dylan Roche
Sezzle, founded by Charlie Youakim, stands out in the growing buy-now-pay-later market, offering interest-free payment plans and exclusive deals with top brands like Amazon and Walmart. With ambitions to expand into a financial services hub and shopping destination, Youakim said Sezzle aims to integrate technology across all departments to enhance efficiency and capitalize on global talent, while maintaining a startup mentality and strong partnerships to sustain its growth.
Nobody is saying cash or credit cards are things of the past, but with the rapid development of fintech in today’s modern market, it’s clear that consumers want more options for payment. What’s more, they want plans that let them pay on a realistic schedule (buy now, pay later!) and maybe even take advantage of some special discounts along the way (exclusive deals on top brands!).
With his accomplished background in technology, Charlie Youakim saw the potential for this emerging technology and established Sezzle. “We’re in a really exciting sector of buy-now-pay-later—it’s really become an important payment method,” he said. “BNPL currently represents around 6% of market penetration in the United States in terms of people’s preferred payment method.”
Youakim started his career as an engineer software developer when he finished business school 14 years ago, establishing his first company in the form of a mobile payment app for parking called Passports. He knew he liked working in payment software, but he eventually moved toward retail because he saw it as “the more exciting sector.” Just like that, Sezzle—an amalgamation of the words “sell” and “sizzle”—was established.
“Here are the cultural elements we really believe in: One of those is to act like an owner. One of those is we want to be driven to succeed. One is that we want to be great communicators.”
Buy Now, Pay Later—and Beyond
Even though buy-now-pay-later (BNPL) occupies only about 6% of the U.S. market, Youakim sees huge potential growth, potentially reaching upward of 20% payments market share. “We’re in a growing sector, we’ve got a great high-quality product with great margins, and we’re growing at a pretty rapid clip,” he observed. Currently, Sezzle has 55% gross margins and 35% revenue growth. Its total revenue for 2023 was about $160 million.
Even with BNPL’s potential to grow within the payments market share, Youakim wants to see Sezzle do more. While the app currently lets users set up payment plans when they buy goods—all without any interest—and get access to exclusive deals with brands like Amazon, Walmart, and Target, among many others, Youakim had a bigger vision.
“We want to become a financial services hub for the customer,” he said. This would entail bringing on more banking options for the customer to make Sezzle their home base for financial services and products. It could also make the app a shopping destination, so it becomes, in Youakim’s words, a “combo platter” of shopping and banking.
“Customers, when they download the Sezzle app, can use it for banking, of course, but they can also use this for searching for great discounts and places to use our payments products, while also saving themselves lots of dollars in the process,” he said. “Let’s say you’re shopping in a Macy’s. Our vision is that when you check out, we automatically apply discounts that we found for you on the web and save you 10 bucks along the way while you’re shopping with us.”
“The team is really driven to drive gross margin north at a higher rate than our operational expenses as we grow the business.”
A Startup Mentality
For a company to create software like this, Sezzle can’t limit technology to any single department or team, Youakim explained. Tech has to be something that all team members are involved in. “In the old era of technology, a lot of companies used to have a tech team, and it’d be a shared resource across the entire company, but it would also be working on your products and services,” he said. “We don’t follow that model. What we do instead is, within our budgetary processes, I require our teams that are traditionally non-tech to add tech to their team, and I really push for it.”
Of course, he admits, he doesn’t really have to push that hard—once his team members see results, they’re usually happy to take this approach. Typically non-tech units, such as marketing and sales, are automated as much as possible making them much more proficient.
Efficiency in hiring is another priority that benefits Sezzle. With its remote-first approach to business, the company can tap into talent abroad, where there’s a lower cost for human resources, all without ever eliminating positions in the United States.
“If we’re able to hire teammates in other locations that have a lower cost to bring on to the company, everyone wins,” Youakim said. “We can treat everyone better within the company because we’re able to spread out the benefits across our team members.” South America, specifically Colombia, has proven to be an important location for Sezzle’s workforce, with about 40 new employees brought on within a six-month period of time.
Even with growth, Youakim believes it’s important to maintain a startup mentality, where he as a co-founder and CEO isn’t afraid to roll up his sleeves and do work beyond his job as owner, setting an example for the 300 people he has in his employ.
“The startup mentality helped us get through some pretty tough times as a company,” he said. “And now that we’re in this really good time for us, I think we can keep the momentum carrying forward.”
He also believes in the value of pushing and challenging everyone within Sezzle—it’s never about simply just getting the job done. “What I find is that employees love to be challenged. They love to make the day fly by because they’ve got enough work,” he said. “People get immersed in what they’re doing, and they aren’t clock-watchers; they’re willing to put in the extra here and there to ensure a project gets done or a deadline is met. And everyone supports each other to go the extra mile.”
“When you’ve got a high-performing partner in the space, you have to fight to keep that relationship.”
Competition, Partnerships and Transparency
This same desire for challenge extends to the way Youakim views competitors, such as Klarna or PayPal. When he sees the successes of companies similar to his, it makes him realize he wants to do better. He looks at what they’re doing right and where they might need improvement, all so he can ensure Sezzle serves customers in the best way possible.
Just as important as competition, however, is partnership. “Choosing the right partnerships is really important for a company and its ongoing success, no doubt about it,” he said, noting that Amazon has been a key partner for web services from the very beginning, as has Google for internal operations, and the warehouse line provider Bastion, which provides capital. Youakim sees managing these relationships as crucial to success.
The final part of Youakim’s vision for leadership comes down to consistency and being able to adequately communicate the values you have to everyone on your team. This, he says, will ensure that everyone on your team is moving forward together. He values the wisdom of business leaders such as Warren Buffett, particularly with regard to one of his oft-cited quotations: You can hold a rock concert, and that’s OK. You can hold a ballet, and that’s OK. But don’t hold a rock concert and advertise it as a ballet.
“Basically, say what you are and do what you are,” Youakim said. “Tell your team, be transparent, let them know what your cultural values are that you believe in. … You can adjust, but don’t be a flip-flopper. Make the team clear on what you expect and push forward.”
