RevUP Caribbean hosts landmark weekend retreat 7.0, graduating 13 cohort 7 founders

 RevUP Caribbean Limited, the English-speaking Caribbean’s virtual business incubator, successfully concluded Weekend Retreat 7.0 on Sunday, July 12, 2026, at Couples Sans Souci in Ocho Rios, Jamaica. 

The three-day event, themed “What It Takes to Be a Great CEO,” brought together 13 graduating Cohort 7 founders for an intensive, immersive programme of learning, investment readiness preparation and peer connection, marking the climax of RevUP Caribbean’s seventh five-month incubation programme.

The Retreat, held from July 10 to 12, 2026, featured five CEO Excellence Pillar sessions led by accomplished founders and business leaders from Jamaica, Trinidad and Tobago and Silicon Valley, a competitive Elevator Pitch Event, panel discussions and a Closing Ceremony. The Development Bank of Jamaica served as a strategic partner, with additional support from a coalition of private sector sponsors whose combined investment of over US$40,000 made the Retreat possible.

Since its founding in 2021, RevUP Caribbean has trained over 185 founders across the English-speaking Caribbean, with an investment track record of US$3 million deployed through its affiliated angel investor network, FirstAngels Caribbean. Retreat 7.0 marked a significant milestone, introducing for the first time a cohort of paying RevUP alumni and specially invited sponsors as active participants in the learning experience alongside the graduating cohort.

Sandra Glasgow, Managing Director, RevUP Caribbean Limited, said, “This was our most ambitious Retreat to date. We raised over US$40,000 from our sponsors to bring these thirteen founders to Couples Sans Souci for three days of world-class mentorship from people who have built real businesses in real Caribbean conditions. What struck me most this weekend was the quality of the conversations; the honesty from our speakers, the courage from our founders, and the generosity of every person in that room who gave their time and expertise freely. Cohort 7 graduates today into a community of 185 Caribbean founders who have walked this path before them. That community does not end at graduation.”

The Five Pillars of CEO Excellence

Retreat 7.0 was structured around five Pillars of CEO Excellence, each led by a practitioner with direct experience of the challenges Caribbean founders face:

•       Pillar 1: Strategy was led by Kirk-Anthony Hamilton, Founder and CEO of Infiniti Partnership Inc. and Co-Founder of Tech Beach, whose platforms have facilitated over US$300 million in Caribbean investments and connected participants controlling in excess of US$140 billion in equity and investment capital. A 2015 Obama recognition recipient and World Economic Forum participant, Hamilton challenged founders to ask not how hard they are working, but where they are choosing to play.

•       Pillar 2: Talent was led by Simone Clarke-Cooper, Founder and CEO of SimSpeak Communication Services Limited, former Chief Communication Officer at GraceKennedy Limited and Jamaica Chamber of Commerce Entrepreneur of the Year. Clarke-Cooper addressed the critical challenge of attracting and retaining talent without a corporate budget, and the cost of delaying hard decisions.

•       Pillar 3: Sales was led by Dominique Himiob, Founder and Managing Director of Amāre Probiotics Limited, Trinidad and Tobago, who built a nationally distributed probiotic food and drinks brand from a kitchen in 2015 in a market she had to create from scratch. Himiob’s session drew on her journey to distribution through Hadco Limited, one of Trinidad and Tobago’s leading distributors.

•       Pillar 4: Execution was led by Dwayne Samuels, Co-Founder and CEO of Samelogic, a Silicon Valley-based agile feedback experimentation platform. A Mandeville, Jamaica-born entrepreneur who raised institutional venture capital and was recognised by the United Nations as one of the 100 Most Influential People of African Descent in Business in 2018, Samuels challenged founders to build execution systems rather than simply work harder.

•       Pillar 5: Scaleup and Professionalisation was led by Audley Reid, Co-Founder and CEO of R.A. Williams Distributors Limited, whose company listed on the Junior Market of the Jamaica Stock Exchange in 2024, raising J$400 million in an oversubscribed IPO. Reid’s session addressed the systems, governance structures and financial discipline required to grow a founder-led business beyond its founder.

All five Pillar sessions were facilitated by Adrian Tait, Partner and Head of Advisory Services at PricewaterhouseCoopers Jamaica, and Toni-Ann Reid, Senior Manager, Advisory Services, PwC Jamaica, who guided panel discussions and Q&A sessions with the founders throughout Saturday and Sunday.

According to Adrian Tait, Partner and Head of Advisory Services, PricewaterhouseCoopers Jamaica, “It was a privilege to be in that room. The quality of thinking these founders demonstrated across both days, the strategic questions they asked, the honesty they brought to the exercises, the way they engaged with each other and with the speakers, was genuinely impressive. The RevUP programme is clearly building more than businesses. It is building leaders.”

 Elevator Pitch Competition

The Retreat opened on Friday, July 10, with the Elevator Pitch Competition. All 13 Cohort 7 founders competed before a judging panel comprising the five CEO speakers and the PwC facilitators. Cash prizes were awarded as follows:

• First Prize: USD 1,200 — Dennis Eccleston, Synergy Performance
• Second Prize: USD 1,000 — Dr. Judlyn Telesford-Checkley, Grenada Grows
• Third Prize: USD 750 — Dwayne Harris, MeetAbie

Dominique Himiob, Founder and Managing Director, Amāre Probiotics Limited, Trinidad and Tobago, stated that what moved her most was how much these founders already knew. “They asked sophisticated questions about category creation, about first-customer strategy, about building a sales engine that does not depend on the founder. These are not beginners. They are future leaders of the Caribbean economy, and they are thinking like it,” she opined.

Audley Reid, Co-Founder and CEO, R.A. Williams Distributors Limited, shared, “When I look back at where R.A. Williams started, in a small pharmacy in Clarendon in 2009, and where we are today, nationally distributed, publicly listed on the JSE, exploring regional expansion, I know that the single biggest shift was the decision to professionalise. To build systems instead of relying on myself. That journey did not happen overnight, and it was not comfortable. But it was the most important decision I ever made as a CEO. I hope that is what the founders took from Saturday morning.”

Sponsors and Partners

Weekend Retreat 7.0 was made possible through the generous support of the following partners and sponsors:

• Strategic Partner: Development Bank of Jamaica
• National Commercial Bank Jamaica Limited
• Sagicor Investments
• Caribbean Climate-Smart Accelerator
• Restaurant Associates Limited
• 7Krave
• Lifespan Spring Water
• Pan Jamaica Group Limited and CB Facey Foundation
• Rocketship
• Liberty Business
• GraceKennedy Financial Group
• The JMMB Group
• EZTix
• Radeos