(Dr.Naeem Ul Hassan)
In today’s challenging business environment, several female FinTech entrepreneurs have emerged, choosing to transition from promises of traditional career success to carving out new frontiers and transforming the way business is done by disrupting socio-cultural norms. Dawn Nelson is one such pioneer. Dawn is getting noticed for her revolutionary initiative to drive digital payment education in the Caribbean using school transactions with her start-up MyCashlessClass.
“My years of experience working with players in the FinTech industry in the Caribbean showed very clearly that having an idea is simply not enough. Even being able to prove that your solution does what it says it will do is not enough.”
She continued, “Fintechs are usually not just fighting to find the best path to achieve scale and impact in an ecosystem where ease of doing business is still elusive, but are also swimming against the grain of entrenched resistance to digital solutions based on inherent mistrust of anything digital that you find in the Caribbean.”
Despite successfully implementing several prominent digital payment implementation projects at national scale in Trinidad and Tobago, Dawn readily admits that converting the school environment to one that embraces new digital options is by far her greatest challenge to date. As the Founder and CEO of MyCashlessClass, a digital marketplace with the vision for all school offices and school cafeterias to be located in an easily accessible one stop shop,” Dawn shared, “I soft launched the concept in late 2024. I conducted several focus groups with local schools and a few cafeterias to understand exactly what mattered to them. I was stunned by how many school administrators and teachers view digital solutions with a degree of fear. I also found that there were many of them who did not use digital solutions in their own lives.”
MyCashlessClass aims to make school transactions easier, cheaper and more convenient for working parents while teaching kids the value of financial responsibility and helping them to become digitally comfortable. The school office and cafeteria benefit from greater efficiency in their record keeping, savings when it comes to the reduction in printing costs and also saving time from trying to contact parents to deal with last minute school transactions that were missed. The platform is free for school offices and cafeterias to join and the MyCashlessClass team takes care of creating the digital stores.
“MyCashlessClass allows parents to make purchases from the digital school office at any time from the comfort of their computer or phone, just like shopping on Amazon. Students can use their MyCashlessClass Student cards to tap and pay in school. They don’t need a phone.” The school office and cafeteria scan the cards using the secure MyCashlessClass app. Payments are processed through Visa, the global payment powerhouse, using Cybersource. No card details are stored and all transactions are encrypted using tokenization.
Dawn credits her motivation behind launching this revolutionary project to following the old adage; Necessity is the mother of all invention.
“I had dropped my son off at school in mid 2024 and arrived at work when he called to say, ‘Mom, yesterday was the last day to pay for something and the event is this morning, and I cannot attend because I didn’t submit the form and pay the money.’ So here I was, leading digital payment projects at a country level, but as a parent, I couldn’t send money to my son in school in real time. That didn’t sit right with me and that was the birth of MyCashlessClass.”
Dawn credits her creativity to her diverse career background, observing service delivery in more mature markets, embracing design thinking and always keeping excellent customer service at the forefront. Starting her career as a medical representative allowed her to travel extensively during her early chapter; Germany, Luxembourg, the United Kingdom, the Eastern Caribbean, Canada, and the United States.
By the age of 29, she held her first managerial position as the Marketing Administration Manager of Barbados Mutual, now Sagicor, and fully crossed the bridge into the business world. She gained experience working in other sectors; Supply Chain logistics, Health Care, and IT consulting, before eventually taking her place as an expert and leader in restructuring government entities for Digital Payment implementation. She often led the design team for the public facing service interface as well. “Working across many diverse fields honed my inner consultant and shaped my philosophy of always being open and curious. When it comes to harnessing what will drive the stakeholders’ perception of value, you need to embody adaptability and versatility in different scenarios. It was lessons learnt along my journey from medical representative to entrepreneur that gave me that lens. Achieving successful digital payment transformations wouldn’t have been possible without it.”
Dawn makes time for mentoring and inspiring future corporate leaders. She has spoken at numerous conferences, such as the Clico Youthpreneurship Conference 2025, AMCHAM’s T.H.I.S conference and NEDCO’s three-day business forum, where she discussed navigating today’s digital world.
She notes that with modernization and expansion of globally available financial systems, the trend toward digital-first banking, and the growing focus on financial inclusion, the scope for FinTech entrepreneurship is rapidly growing. Entrepreneurial role models are crucial in guiding, inspiring, and highlighting the skills and mindset required to build successful businesses. Building a profitable FinTech business in today’s environment requires all the expected due diligence; fully comprehending the applicable laws and regulations, prioritizing security and customer service from the first day, fully automating deployment procedures where possible, including leveraging AI; and embracing continuous testing to drive service resiliency.
Dawn offers additional guidance to help future female FinTech entrepreneurs achieve career success.
“Targeting the disruption of inefficient legacy structures is the best way to design an impactful solution. By stepping out of cultural comfort zones with empathy and a customer first mindset, you can grasp opportunities that not only shape your character and prepare you for future success but that also change lives in real and tangible ways. Have the guts to do it. Do not be afraid to pursue your goals.”
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