Xplorer Ishara Wickramasinghe

Finding empathy in entrepreneurship

When we launched our new brand, we gave every Xplorer a personalised founder card to represent their individual role in helping shape the future of our company. Why? Because having a strong ownership mindset is part of our cultural DNA. All of us think and act like founders – because, while helping people succeed is what unites and inspires us, it’s ownership and entrepreneurship that defines who we are.

Ishara Wickramasinghe is no exception to this founder mindset. A UX designer for Xplor Pay, Ishara has been developing his inner-entrepreneur since he was a kid – literally. 

“I built my first commercial web application at 11 years old, and got paid for it too,” he says. “This might sound silly, but I think I’ve been an entrepreneur since my young days.”

Ishara’s young days were spent in Kurunegala, Sri Lanka: a town with a population of 30,000 (and a hundred times that in coconut trees). Ishara had access to a computer from about four years old because his older brother scored high in an exam and was gifted a computer from their father’s work. 

Ishara also grew up with driven entrepreneurs around him – namely his late grandmother who was widowed at a young age and had to raise his mother and aunt alone. 

“She was not from a wealthy background. Yet, she managed to take care of her kids by running a small business cooking and delivering breakfast food items to shops. She spent most of her time in front of a smoky wood fired stove and later developed asthma as a result. But, she never complained – not even on those days when she was finding it difficult to breathe. Yet, despite all that pressure, she’s the kindest person I’ve ever known.”

After Ishara got his early start with a computer, he moved onto various freelancing development and designing jobs, and used that income to sustain his education. 

“I knew since I was a little kid that my parents worked so hard to support us, so this was my way of taking some of the pressure off them,” he says.

Beyond freelancing, Ishara has spent his career in various development and UX roles around the world. He’s worked in the Middle East, Sri Lanka and now works in New Zealand, and has worn many hats: Software Engineer, Frontend Developer, Solutions Architect, UX Architect, Branding Consultant, and Creative Team Lead for organisations like Emirates Airlines, Kelloggs, Coca-Cola, Formula 1 and Expedia. 

Despite working for larger brands, his passion for entrepreneurship remained constant. In 2019, Ishara founded a software development company called Creative Tribe, a company that facilitates IT-related local job opportunities in his hometown. He noticed a void in tech jobs where he grew up, as almost all of the software development companies in Sri Lanka are based in the commercial capital of Colombo – which is a three hour commute on overcrowded public transportation. That means employees wanting to make a living for their family ultimately lose out on the time they could be spending with them.

“These people commute hanging to the footboards of trains and buses, betting against their lives. This commute in itself sucks the productivity out of people,” he says. “They leave their homes before the crack of dawn and they come back home quite late into the night.”

Ishara says his hope is to turn his small hometown into an IT hub like the commercial capital, Colombo, and this small but mighty operation is the first step toward this journey. In the last three years, the company has undertaken 15+ software development projects and currently employs a number of full-time permanent employees alongside fixed-term contractors.

Like many Xplorers who previously owned businesses, Ishara is able to apply his freelance and entrepreneurial experience to challenges he encounters at Xplor, and identify real pain points that customers face every day. One truth he’s recognised not only in his work, but also that of his clients, is balancing running a business from a place of passion alongside the inescapable and difficult admin-related tasks.

“Oftentimes, these tedious tasks curtail the passion and the enjoyment of business owners. What I love about Xplor is our solutions take care of most of these tedious tasks like administration, billing and correspondence so more businesses can focus on what they truly love doing,” he says.

It comes as no surprise, then, that the Xplor value that Ishara connects with is “build for people.”

“My interpretation of ‘build for people’ is being empathetic and forgiving in the experiences that we tailor,” he says. “It’s important to share and understand the feelings of our customers in order to understand their pains and challenges. It’s also important to acknowledge that people are prone to making mistakes and therefore the experiences we tailor should be easy to follow with minimal room for error.”

People, it turns out, is also why Ishara chose to work for Xplor.