HeadOffice, a Jamaican fintech startup, emerged as the winner of the Fintech Islands Experience 2025 (FiX25) Startup Pitch competition, securing the grand prize of a non-dilutive cash award of US $10,000 to inject into the business.
Held on the final day of FiX25, the largest international fintech event in the Caribbean, this year’s Startup Pitch showcased some of the region’s most innovative fintech entrepreneurs. The Startup Pitch competition was open to early-stage fintech founders with company offices in the Caribbean or founders residing in the Caribbean who have raised less than US $1.5 million from investors’ funding. The nine finalists, selected through a rigorous accelerator program, were evaluated based on their market validation, product innovation, business model, and ability to tell their stories with authenticity and passion.
Hailing from various Caribbean nations such as Barbados, Jamaica, and Trinidad, each finalist had four minutes to pitch live on the main stage. They presented to a distinguished panel of judges and an audience of international fintech stakeholders. The judges included Chris Cochran, Executive Director of Entrepreneurs Across Borders; Nneka Etoniru, Executive Vice President of Global Brand Strategy at Avenue Z; Simon Johnson, Investment Officer at IDB Lab, a subsidiary of the Inter-American Development Bank; Ife Badejo, Founder and Chief Executive Officer (CEO) of Islandpreneur International LLC; Ulili Onovakpuri, Managing Partner at Kapor Capital; and Spragga Benz, Performing Artist and CEO of Redsquare Productions LLC.
Revolutionizing Business Management with HeadOffice
Khary Sharpe, Founder of HeadOffice, captivated the judges with his vision of a “super app” designed to simplify accounting and business operations. Describing HeadOffice as the “future of accounting and business management”, Sharpe pointed to the app’s capability to streamline various business tasks, including payroll and invoicing for retainer clients, helping to redefine business management for companies across the Caribbean.
“HeadOffice is an all-in-one accounting platform that automates complex financial operations, saving businesses both time and money,” Sharpe said. “It takes the average accountant nearly 268 hours annually to prepare and file tax returns. HeadOffice automates everything—from invoicing clients and tracking expenses to calculating taxes and preparing financial reports—turning months of work into minutes.”
Celebrating the Finalists
David Dick, Co-Founder and CEO of Monytri, was awarded second place and a non-dilutive cash prize of US $5,000. Monytri is a fintech platform designed to revolutionize the way people engage with financial assets. The Monytri app aims to connect users to major brokers, banks, and financial institutions, allowing them to gift stocks and exchange-traded funds seamlessly.
Meanwhile, third place went to Raquel Seville, CEO and Founder of Dataffluent, a research and data science company focused on financial insights and modeling for publicly traded entities in developing and emerging markets. She received a non-dilutive cash prize of US $2,500.
Support and Mentorship
This year’s Startup Pitch was held in partnership with The TimePledge Network, a global initiative promoting financial inclusion and entrepreneurship. TimePledge provided mentorship to the finalists, with renowned fintech expert Matteo Rizzi conducting training sessions to prepare them for the stage.
The finalists also benefited from words of wisdom from the winner of the 2024 Startup Pitch, Jarryon Paul, the founder and Chief Executive Officer of Sunshine, the world’s first stablecoin remittance exchange. Paul, while giving an update on Sunshine’s performance, stressed the importance of authenticity, building deep relationships, and prioritizing personal growth as key drivers of entrepreneurial success.
“From last year to this year, we’ve nearly doubled our membership, growing from just over 1,000 to around 2,000 members. Our revenue has increased, our team has expanded, and we’ve now moved beyond Trinidad and Tobago,” he reported.
Caribbean’s Fintech Future is Bright
Meanwhile, the Co-founder and Chief Technical Officer (CTO) of Fintech Islands, Curt Persaud, reflecting on the competition, called it a success. He noted that the quality of ideas that were pitched speaks to the considerable talent and innovation present in our region.
He added, “We are dedicated to supporting the development of early-stage fintechs by offering platforms such as this competition and mentorship. These resources aim to assist them in transforming groundbreaking ideas into innovative solutions that will influence the future of financial technology in the Caribbean and beyond.
Saved as ‘winner’
(Center) Winner of the FiX25 Startup Pitch competition, Jamaican Khary Sharpe, Founder of HeadOffice, celebrating his US $10,000 win with (from left) Matteo Rizzi, founder of The TimePledge Network; Co-founder and CEO of Fintech Islands, Allison Hunte; (fourth from left) Co-founder and CTO of Fintech Islands, Curt Persaud and Andrew B. Morris, Founder and CEO of The Fintech Agenda and Chief Content Officer, Fintech Islands.
Saved as ‘second place’
(Center) David Dick, Co-Founder and CEO of Monytri, secured second place in the competition with a non-dilutive cash prize of US $5000.
Saved as ‘third place’
(Center) Raquel Seville, CEO and Founder of Dataffluent, was awarded third place and a non-dilutive cash prize of US $2500 in the keenly contested Startup Pitch competition.
