Don't Let Your Location Limit You - Stories from a Remote Work Pro, Stephen Stanbury

Don't Let Your Location Limit You - Stories from a Remote Work Pro, Stephen Stanbury

Nine years of remote work, two layoffs over video calls, and a journey from Jamaican radio journalist to Foundpreneur — Stephen Stanbury has seen it all, and he's not holding back. Stephen Stanbury went from getting a letter of termination two months into his first job to becoming a Director of Operations at a fully remote company — all built on grit, Fiverr voiceovers recorded from his closet, and a refusal to let his Caribbean location be a ceiling. In this episode, Stephen unpacks what the remote work landscape really looks like in 2026, what mistakes Caribbean professionals keep making, and why your LinkedIn profile might be the most important job application you never sent. He also shares the story behind his new venture, Foundpreneur — a platform dedicated to spotlighting Caribbean entrepreneurs on a global stage. What we cover: * How Stephen went from freelancing on Fiverr (using his company's internet) to Director of Operations — and what it really takes to climb in remote work * Why your LinkedIn profile, personal brand, and AI searchability are now more important than your resume * How to stand out in a global applicant pool when everyone has an AI-optimised CV * The Caribbean Remote Work Conference 2026 — and why you need to be there Ready to build your remote career on your own terms? Head to theremoteislander.com [https://theremoteislander.com/] for resources, episode notes, and more. Guest: Stephen Stanbury — Remote Work Veteran, Personal Branding Strategist, and Founder of Foundpreneur | Find him on LinkedIn: https://www.linkedin.com/in/stephenstanberry/ [https://www.linkedin.com/in/stephenstanberry/] You can find all of our links here: https://linktr.ee/theremoteislander [https://linktr.ee/theremoteislander] Links mentioned: BairesDev [https://applicants.bairesdev.com/register?referrer=pM9DGdd4] Keron Rose's Blog [https://keronrose.com/are-you-struggling-to-get-paid-by-international-clients-in-the-caribbean/] EF SET 15-minute test [https://www.efset.org/quick-check/] *Edit: Payoneer has stopped its referral program but you can sign up for an account here [https://www.payoneer.com/].

7 Remote-First Companies That Hire Globally — Including Where You Are (Ep. 24)

Seven companies. Zero geographic restrictions. All hiring globally - and yes, that includes you. In this episode, I break down seven remote-first companies that are genuinely worth your time as a Caribbean or LATAM professional.  Not companies that "allow" remote work - companies where remote is the foundation.  From the creative-as-a-service world of Superside to the radical salary transparency of Buffer, this is your no-fluff shortlist of employers who have already built the infrastructure to hire you, pay you, and support you across borders. Key topics covered: * Why remote-first culture matters more than remote-friendly policy — and how to tell the difference * Automattic, GitLab, Zapier, Superside, SafetyWing, Remote.com, and Buffer: what each company does and what to expect going in * Why written English is your competitive advantage — and how to sharpen it before you apply * Three practical principles for actually landing a role at any of these companies Ready to take your remote career seriously? Start at theremoteislander.com. You can find all of our links here: https://linktr.ee/theremoteislander [https://linktr.ee/theremoteislander] Links mentioned: BairesDev [https://applicants.bairesdev.com/register?referrer=pM9DGdd4] Keron Rose's Blog [https://keronrose.com/are-you-struggling-to-get-paid-by-international-clients-in-the-caribbean/] EF SET 15-minute test [https://www.efset.org/quick-check/] *Edit: Payoneer has stopped its referral program but you can sign up for an account here [https://www.payoneer.com/].

Stop Applying to the Wrong Jobs — Remote Work Guide for Caribbean Professionals (Ep. 23)

Stop wasting time on job boards that weren't built for you — here's exactly where Caribbean professionals should be looking for legitimate remote work that pays in USD. If you've ever applied to a "remote" job only to discover it's US-only buried in line four of the description, this episode is for you. I break down the actual platforms, search strategies, and scam red flags — no fluff, no gatekeeping — categorized by industry so you can move fast and move smart. In this episode: * Why LinkedIn and Indeed fall short for Caribbean job seekers — and how to use them smarter * 9 international remote job boards that genuinely mean worldwide * Caribbean-specific platforms you probably haven't bookmarked yet * How to spot scams before they waste your time * How to get paid in USD from the Caribbean (Wise, PayPal, Payoneer and more) * A 6-step action plan to execute this week, completely free Your remote career starts with the right map — head to theremoteislander.com for more resources to help you get there. You can find all of our links here: https://linktr.ee/theremoteislander [https://linktr.ee/theremoteislander] Links mentioned: BairesDev [https://applicants.bairesdev.com/register?referrer=pM9DGdd4] Keron Rose's Blog [https://keronrose.com/are-you-struggling-to-get-paid-by-international-clients-in-the-caribbean/] EF SET 15-minute test [https://www.efset.org/quick-check/] *Edit: Payoneer has stopped its referral program but you can sign up for an account here [https://www.payoneer.com/].

From Survival Mode to Remote Career: Oshido Christie on Careevo's Method (Ep. 22)

Landing a remote job from the Caribbean in 90 days or less — is it actually possible? This episode breaks down exactly how. Sacha sits down with Oshido Christie, Remote Career Strategist and Chief Operations Officer at Careevo, to talk about what it really takes for Caribbean professionals to break into the international remote job market. Oshido shares how he went from selling resume templates on Etsy to building a full ecosystem — job board, AI-powered tools, and coaching — designed to keep Caribbean professionals home while earning what they deserve. No fluff, no gatekeeping — just the real process. In this episode: * Why mindset is the biggest barrier to landing a remote job (and what to do about it) * The 3-part positioning system: resume, LinkedIn, and intro script * How Careevo's Job Alignment Tool helps you apply smarter, not harder * What the Authority Suite is and who it's built for * The Caribbean Remote Job Board: a centralised hub coming to change the game Ready to start your remote career journey? Head to theremoteislander.com [https://theremoteislander.com/] Guest: Oshido Christie, Remote Career Strategist & COO at Careevo TikTok/Instagram: _.oshido._ | LinkedIn: Oshido Christie | YouTube: https://www.youtube.com/@UC387mOsaN5rNkRGmm-1fXEA You can find all of our links here: https://linktr.ee/theremoteislander [https://linktr.ee/theremoteislander] Links mentioned: BairesDev [https://applicants.bairesdev.com/register?referrer=pM9DGdd4] Keron Rose's Blog [https://keronrose.com/are-you-struggling-to-get-paid-by-international-clients-in-the-caribbean/] EF SET 15-minute test [https://www.efset.org/quick-check/] *Edit: Payoneer has stopped its referral program but you can sign up for an account here [https://www.payoneer.com/].

How to Get Hired by BairesDev in 2026: Caribbean & LatAm Guide (Ep. 21)

BairesDev is still one of the best doors into USD-paying remote work from the Caribbean — but the way in has changed, and most applicants don't know it. In this episode, I break down the 2026 version of BairesDev: what's new in their application process, who they're actually hiring (hint: it's not just developers), and how Caribbean and Latin American professionals can position themselves to stand out in a pool of over 2.4 million applicants a year. Straight facts — what you need to know before you apply. What's covered: * How BairesDev's AI-driven talent matching system actually works * Who's being hired in 2026 — including non-technical roles in HR, marketing, and finance * Why Caribbean professionals have a structural nearshore advantage * 5 practical tips to sharpen your application right now * The truth about the talent bench and what silence really means Ready to go remote? Start at theremoteislander.com [https://theremoteislander.com/] You can find all of our links here: https://linktr.ee/theremoteislander [https://linktr.ee/theremoteislander] Links mentioned: BairesDev [https://applicants.bairesdev.com/register?referrer=pM9DGdd4] Keron Rose's Blog [https://keronrose.com/are-you-struggling-to-get-paid-by-international-clients-in-the-caribbean/] EF SET 15-minute test [https://www.efset.org/quick-check/] *Edit: Payoneer has stopped its referral program but you can sign up for an account here [https://www.payoneer.com/].