A wave of digital transformation is sweeping across Caribbean start-ups as entrepreneurs embrace artificial intelligence (AI) to scale their businesses, improve customer experiences, and streamline operations. Leading this charge is Nadeen Matthews Blair, founder and CEO of Crescent Advisory Group, whose AI training module in the prestigious RevUP Caribbean Incubator Programme has yielded impressive results for participating entrepreneurs.

Less than a year after participating in Blair’s “Going Digital and AI” module as part of the RevUP Incubator’s fifth cohort, entrepreneurs report significant business improvements and competitive advantages through strategic AI implementation.

ChatFlow

Michael Mullings, CEO of ChatFlow, a company specialising in AI-powered customer support solutions for businesses across the Caribbean, credits the training with helping his company scale operations.

“Since the RevUP ‘Going Digital’ module, we’ve doubled down on our mission to improve customer support across emerging markets using practical, AI-powered solutions,” Mullings said.

His company has implemented several key innovations inspired by Matthews Blair’s training. “One major shift we made was building our own internal AI onboarding agent — a Claude Sonnet and OpenAI-powered virtual assistant that trains our team on platform features and security protocols,” Mullings explains. “Rather than relying on manual training spread across drives, we digitised it into an intelligent agent that can onboard new team members 24/7, saving us hours of internal set-up time.

“Even outside our own product, we’ve taken Nadeen’s advice to test small, scale fast. Tools like Claude and Notion AI have been crucial in helping us generate content, write knowledge base articles, and even script customer training videos. Every hour saved on repetitive content is time we invest back into growth and relationships.”

The results speak for themselves—ChatFlow recently won the Jamaica Stock Exchange Pitch Competition, has pitched to members of FirstAngels Caribbean, and is in due diligence for an investment by the group.

“I appreciated the push around digital storytelling. I owe a lot of the clarity I gained around digital positioning to Nadeen’s workshop,” he added.

Pivotal DSS

For Dr Nik Pearson, founder of Pivotal DSS, a decision support platform designed to help manufacturers and distributors grow profitably without the need for in-house analytics or complex IT systems, AI has become a “virtual team member”, supporting everything from strategy to execution. “I’ve used ChatGPT, Claude, CoPilot and some other lesser-known tools extensively to accelerate everything from persona development and customer messaging to product design, grant applications and investor materials,” Pearson explained. “What I’ve found most valuable is how AI enables me to keep momentum even when resources are tight. It helps me think better, work smarter and stay focused on delivering value to clients.”

Since participating in the RevUp programme, Pivotal DSS has secured funding through the Microsoft for start-up programmes.

The Brand Mint

The impact extends beyond tech companies. Tomekha McCarthy, CEO of The Brand Mint, which specialises in artist management and music marketing, has incorporated AI as a supportive tool to translate strategic thinking into structured outputs more efficiently.

“Given the multifaceted nature of our work—from artiste management to music marketing and education—it’s proven useful in accelerating the process of getting our complex ideas into a clearer, more workable format,” McCarthy stated.

While maintaining their distinctive voice and authenticity, Brand Mint has found AI valuable for overcoming “blank-page moments” and exploring initial structures for content development.

Showfa Express

Showfa Express, led by CEO Jamie Hall, is redefining last-mile logistics and e-commerce in Jamaica by embedding AI directly into its operational core. From fleet routing and staff scheduling to partner growth and platform development, artificial intelligence is baked into most layers of the business.

At the centre is Showfa AI, an internal agent built into the company’s API stack and operating system. It analyses, categorises, and reconciles thousands of customer and driver transactions in real time each week, automating what used to take hours and ensuring speed, accuracy, and accountability at scale.

On the e-commerce side, Showfa AI dynamically generates and tests product descriptions, marketing copy, and layout options to help corporate partners drive more sales and engagement through the company’s Pages platform.

“We’re not experimenting. We’re executing,” said Hall. “AI is helping us scale efficiently without losing control. It’s a core part of how we operate.”

Expert-led training makes

Matthews Blair’s module within the RevUP Programme focuses on helping entrepreneurs prioritise and evaluate technology investments, leverage AI safely for business growth, and gain hands-on experience with AI tools tailored to real-world business scenarios.

“What sets successful AI implementation apart is having a structured approach to assessing and selecting high-impact digital investments based on criteria like ROI, scalability, and alignment with business goals,” said Blair. “Our training emphasises not just the technology, but the strategic thinking behind digital transformation.”

With over 20 years of experience in strategy, AI and digital transformation at organisations such as McKinsey & Company, JPMorgan Chase, and National Commercial Bank Jamaica Limited, Matthews Blair brings world-class expertise to Caribbean businesses.

New opportunities

Applications are now open for the sixth cohort of the RevUP Caribbean Incubator Programme, offering Caribbean-based entrepreneurs with high-growth start-ups 90 hours of management and investment readiness training, one-on-one coaching, local and international mentorship and access to angel investors and grants. Female founders are especially encouraged to apply. The application deadline is May 30.

For companies and executives looking to begin or accelerate their AI journey, Nadeen Matthews Blair’s boutique advisory firm Crescent Advisory Group offers specialised services in AI strategy development, implementation, and hands-on training for teams, leaders and boards.

“We help businesses demystify AI and create practical adoption plans that deliver measurable results,” explained Matthews Blair. “From identifying the right AI tools for your specific challenges to training your team and measuring ROI, we provide end-to-end support that transforms AI from a buzzword into a genuine competitive advantage. The success stories from the RevUp programme demonstrate that Caribbean businesses don’t need massive budgets to leverage AI effectively—just strategic guidance and a willingness to innovate.”