About Us

Our Company

Pineapple, formerly known as Ollo Caribbean, was founded with a bold vision: to empower entrepreneurs and businesses in the Caribbean and beyond by bridging the gap between innovation, education, and execution. We’ve redefined what it means to be a resource for modern businesses by merging the best of digital marketing, startup insights, and recruitment solutions into a comprehensive platform.


As of 2025, Pineapple is your one-stop hub for:


  • Cutting-Edge Digital Marketing Solutions: From expertly managed campaigns to innovative tools like GoHighLevel CRM, we deliver strategies designed to boost visibility, drive conversions, and grow revenue.
  • Corporate English Training: Helping global teams communicate confidently through tailored ESL programs that meet the demands of the modern workplace.
  • Career Development Services: Empowering job seekers with our 9-Step Career Coaching Program to excel in remote opportunities and global markets.
  • Remote Recruitment Services: Connecting businesses with top-tier, trained, and vetted virtual professionals, ensuring the right fit for every role.


We’re also passionate about knowledge-sharing. Our blog delivers the latest insights on marketing, startups, and technology trends, keeping you ahead in an ever-changing digital landscape.


Whether you’re an entrepreneur seeking growth, a business looking to elevate your marketing efforts, or a job seeker aiming to thrive in a remote role, Pineapple is here to support your journey. Together, we can revolutionize how businesses are run, scaling your vision to new heights.


Let’s Build a Smarter Future Together!

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Our Team

Meet the faces behind Pineapple.

Mellesia Lewis

Founder & CEO

Ashley Gayle

Office Manager