Is remote work “gatekeeping” real?
The honest answer Someone applies to a handful of remote jobs, hears nothing back, and decides the people talking about remote work online must be hoarding the real opportunities. It’s a story that keeps circling in Caribbean remote work spaces, and it’s aimed at people I know personally. This piece breaks down where that accusation […]
Pick, Choose and Refuse: Krishna Dewor’s Remote Work Career
Getting to the point where you can pick, choose and refuse remote jobs, rather than take whatever comes your way, comes down to three things: tailoring your resume for every single application instead of using one version, understanding how ATS software filters resumes before a human ever reads them, and building a real LinkedIn presence […]
What Remote Employers Really Look For When Hiring (with Tahirah Webster-Banks)
What remote employers look for when hiring goes beyond your resume. Tahirah Banks-Webster, founder of AlphaNorth Global and ShipSmart, runs her hiring process in three phases: a LinkedIn shortlist, a real skills challenge, then the interview. She’s watching for an active LinkedIn profile, a proper email salutation, thoughtful (not obvious) AI use, and evidence you’ve […]
Remote Jobs From the Caribbean: The Real Gap
Remote jobs from the Caribbean are harder to land not because opportunities don’t exist, but because of four fixable gaps: relying on degrees over demonstrated skills, misunderstanding how ATS systems actually work, leaving default location filters set to the wrong country, and near total invisibility on LinkedIn, where Caribbean professionals make up just half of […]
How to Pay Taxes as a Remote Worker in Jamaica
If you are a remote worker living in Jamaica and earning income from a foreign employer, you are required to pay taxes in Jamaica on your worldwide income. You must register with Tax Administration Jamaica (TAJ), request self-employed status, and file quarterly estimated payments as well as an annual return by March 15. Your employer […]
Remote Work in the Caribbean: Lessons From 9 Years with Stephen Stanbury
Remote work for Caribbean professionals is more accessible than ever in 2026, but success requires more than applying on job boards — it demands a visible personal brand, keyword-optimised LinkedIn presence, and the ability to distinguish remote-first companies from those that merely permit working from home. Caribbean professionals who invest in building an online presence […]
Remote-First Companies Hiring Globally
Remote-first companies hiring globally include Automattic, GitLab, Zapier, Superside, SafetyWing, Remote.com, and Buffer — all of which hire talent regardless of geographic location, with no requirement to be based in the US or Europe. Caribbean and Latin American professionals are eligible to apply, and the infrastructure to pay and employ them across borders already exists. […]
Remote Jobs for Caribbean Professionals That Pay USD
Remote jobs for Caribbean professionals are available on platforms like Hire LATAM, Work Better Now, WeWork Remotely, and South — boards that explicitly hire outside the US. Searching for “worldwide” in location filters and using LinkedIn’s NOT operator to exclude “US only” listings significantly improves results. Payment can be received in USD via Wise, PayPal, […]
Remote Jobs for Caribbean Professionals: The 90-Day Plan with Oshido Christie
Remote jobs for Caribbean professionals are achievable in 90 days or less with the right positioning strategy. The key steps are optimising your resume and LinkedIn for international standards, targeting roles that align with your specialised experience, and applying consistently using a structured daily routine — not mass-applying to every listing. The Caribbean job market […]
Remote Job Search Tips for Caribbean Professionals with Priscilla McClure
Caribbean professionals can land remote jobs faster by targeting fewer, well-researched roles instead of mass-applying, optimising their LinkedIn profile as a digital resume, and entering interviews with specific questions and recommendations that demonstrate they already think like a team member. The Caribbean accounts for just 0.5% of LinkedIn users — and that invisible gap is […]