Sandy Ramasawmy, Ashley Paulus, and Katie Wile of Checkout.com
Sandy Ramasawmy, Ashley Paulus, and Katie Wile of Checkout.com.
| Courtesy of Checkout.com

On November 28, 2022—otherwise known as Cyber Monday—U.S. consumers spent $11.3 billion in online purchases, setting a new record as the biggest shopping day of all time. In this age of e-commerce, buying an item online seems like a simple transaction. However, the reality is much more complex. The ecosystem of online payments moves at lightning speed, evidenced by differing currencies across international borders, rapidly shifting regulations, new technologies, and the turbulent rise of cryptocurrency.

As one of the global leaders in digital payments, Checkout.com processes billions of dollars in global transactions each year—all while continuing to innovate in the face of this fast-changing landscape. Its main goal? To simplify payments and help businesses thrive in the digital economy. In turn, their merchants can focus their energy on the product or service they’ve built rather than on network tokens, digital wallets, or pinless debit.

“We need to be dynamic and agile,” says Katie Wile, a U.S. sales director who has supported the company’s recent expansion within the American market. “In addition to providing a product that is proven to work and work well, we must provide a product that’s customizable—each business is unique and will have its own specific needs.”

Navigating the world of cryptocurrency

It takes a global team to create and implement a service like Checkout.com’s—something businesses that sell a product or service online can’t survive without. Take the Singapore-based Ashley Paulus, Senior Director of Customer Success in Crypto. She leads a rapidly growing team that is pioneering efforts in crypto, which enable merchants—both traditional and web3—to accept cryptocurrency payments.

Many people believe we’re in the middle of a “crypto winter” without much activity or momentum in the payments space. However, Paulus says, Checkout.com and its merchants know cryptocurrency will play a part in the future of payments, which is why they are developing web3 solutions and have already launched a stablecoin settlement option for merchants who don’t want to have to deal with traditional fiat currency—or standard banking hours.

“Fintech firms have historically made up a large portion of our overall merchant base, so it was a natural transition for us to start servicing crypto merchants because of our ability to understand the nuances and dynamic needs of these businesses,” Paulus says.

The bigger challenge for Checkout.com, however, is figuring out how to help more traditional companies navigate the onset of crypto. “A big focus for us is on what kind of products would our web 2.0 and e-commerce merchants be interested in,” Paulus says. “I'm really excited for the crypto-native products that we're building that will help service our web 2.0 customer base.”

Building innovative engineering solutions

The company’s engineers play an oversized role in allowing Checkout.com to stay nimble in such an ever-changing industry. They’re the ones responsible for building a stable platform that’s scalable and customizable for any client, currency, and country.

Mauritius-based DevOps engineer Sandy Ramasawmy is part of a team that builds cloud architectures for safely processing global payments. They also use additional in-house tools to strengthen the resilience of Checkout.com’s technology.

“Failure is inevitable, so we’ve created our own tools for which we write experiments and test our applications, which help create a system that’s secure and able to recover quickly,” he says. “This has been one of the great innovations.”

And according to Ramasawmy, there’s always a new challenge or problem to solve. “Checkout.com is a platform that’s built for speed and ability to scale and adapt to business needs,” he says. “We’re creating exciting engineering work within the payment world.”

Finding success as a Checkout.com employee

Neither Wile nor Paulus had prior experience in the digital payment industry before joining Checkout.com—a testament to how the company values people with transferable skills and a desire to learn.

Paulus, for example, built her career in business operations, including two years in Africa as part of the Peace Corps. Before joining Checkout.com, she also delivered an online subscription model strategy for an e-commerce business in Malaysia, “so I thought I knew everything about payments,” she says. “But my experience was on the merchant side, so I realized very quickly I had a lot to learn.”

That didn’t stop her from growing her career at Checkout.com, where she has been promoted twice since joining in 2020 and now works in a global role. Due to the challenging nature of their work, Paulus says, “People who have a strong work ethic, a growth mindset, and are ready to jump in and make things happen will definitely thrive here.”

Wile, who previously worked in sales in the private jet market, relies on her ability to cultivate strong relationships with merchants when working to bring on new business. But more than that, she leans on her innate curiosity.

“I came in relatively green but hungry to learn,” she says. “The world of payments is complex and the landscape is ever changing. You need to stay curious, always. I’m also being exposed to different lines of business daily, so I believe it’s important to lean in. I’m working with merchants in crypto, real estate, traditional retail, ticketing, etc. It’s vital to understand your audience.”

Wile’s ultimate goal is to thoughtfully sign on the right businesses that can benefit from Checkout.com’s product offering—and she takes pride in seeing clients succeed. “Payments can be a strategic lever to pull,” she says. “Ultimately we are here to help our clients reach that next level in the growth and development of their own particular business. When they win, we win.”

To consistently achieve wins for its merchants, the company empowers its employees to strengthen their skill sets and think outside the box. This often comes into play for those in technical roles such as Ramasawmy.

“There are so many great and enthusiastic leaders pushing and encouraging us to present our ideas,” says Ramasawmy, who has completed technical training and certifications sponsored by Checkout.com. “If you think there are ways of improving our existing systems, they will help you achieve it. This enables us to have the opportunity to make a real impact in the payment world.”

Updated 1/6/2023