George Town, Grand Cayman, Cayman Islands (20 April 2026) – Enterprise Cayman has announced the winners of the 2026 Cayman Islands Business Design Competition, following its sixth annual “Pitch Day” event held on Saturday, 18 April 2026 at The Grand Cayman Marriott Resort. Nine Cayman-born ventures competed for USD $16,000 in cash prizes and wraparound business support services.
Produced by Enterprise Cayman and sponsored by Cayman Enterprise City (CEC), the annual Business Design Competition invites Cayman’s entrepreneurs to showcase their new and innovative business ideas. This year’s competitors were shortlisted from an impressive cohort of over 40 submissions. Programme finalists took part in an intensive series of workshops, project advisor meetings, networking events, and a “Pitch Day” where they presented their final projects to a panel of judges, which included:
Melesia Adderly, Founder and CEO of Women's Haven,
“This year’s cohort truly raised the bar,” said Alyssa Manderson, Programme Manager at Enterprise Cayman. “The creativity, preparation, and quality of execution we saw on Pitch Day were exceptional and reflect the strength of Cayman’s emerging entrepreneurial talent. What stood out most was the calibre of the founders themselves, their growth, confidence, and commitment to building ideas with real potential. We are proud of how far the Business Design Competition has come and excited to continue building on that momentum through our Launch Labs Incubator initiative.”
To date 52 Cayman-born business ventures, including Emailchaser, Island Pet Co., Cogniscent Learning, and CollectSunny, have completed the competition and are part of a growing community of entrepreneurs.
“Our Business Design Competition is about more than just pitching ideas. It’s about strengthening our innovation ecosystem. It’s about empowering individuals to explore real-world problems, validate meaningful solutions, and move one step closer to creating thriving businesses that can succeed both locally and globally,” said Charlie Kirkconnell, CEO of CEC and Chairman of Enterprise Cayman. “We’ve developed and continue to develop a platform where innovators can connect and grow in a welcoming business environment a place where individuals, local businesses, and global ventures can thrive.”
2026 Competition Finalists:
DAYHIREKY – A trusted platform connecting Caymanians and residents to flexible, short-term job opportunities by Erika Wilson
2026 Programme Instructors & Project Advisors: Melesia Adderley, Lauren Christie, Rich Dyer, Isobel Forde, Khurram Hassan, Joshua Hecht, Lance Jefferson, Terita Kalloo, Vlad Logvinov, David Manouchehri, Bartosz Mozyrko, Marta Pires, Stuart Reavley, Cassandra Shea, Michael Staniewicz, Ty Thomas, Ryan Watson, George Wauchope, Omara Whittaker, and Brianna Wilson.
2026 Competition Awards & Winners:
"I’ve pushed boundaries that I didn’t know I had, and it has just been exceptional. I’m so grateful to have been part of this journey, and to Enterprise Cayman for giving me this opportunity to pursue what I think will be an amazing step toward innovation," said Erika Wilson from DayHireKY.
"Throughout this competition I’ve learned that the idea is only really the starting point. The real challenge is creating something that’s clear, defensible, and marketable," said Benjamin Bates from Haven, winner of The Community Impact Award sponsored by HIGHVERN.