The Remote Islander

Ever wondered if your organizing skills could become a business that serves clients around the world, from home?

Remote Islanders, this one is for every boss organizer out there. I sat down with Desi-Ann Gordon, founder of Caribbean Virtual Assistants and known online as The VA Mom. She went from teaching math and crying in traffic to landing her first Upwork job in 2017, then built a training program that helps Caribbean professionals launch their own VA businesses. We got real about what it takes, what it costs, and who this path is (and isn’t) for.

In this episode:

• How a one-page business plan and a new baby started Desi-Ann’s remote journey
• The mindset you need when income is slow and the gas needle is close to E
• Setting boundaries and beating isolation when you work from home
• The software to learn first, and why you should skip the shiny objects
• How her 12-step roadmap and 3-month internship model

Find more episodes and resources at theremoteislander.com.

Website: caribbeanvirtualassistants.com
Email: [email protected]
LinkedIn: https://www.linkedin.com/in/desi-ann-gordon-456003144/

You can find all of our links here:
https://linktr.ee/theremoteislander

Links mentioned:
BairesDev
Keron Rose's Blog
EF SET 15-minute test

*Edit: Payoneer has stopped its referral program but you can sign up for an account here.

What if the real gap between you and a remote job isn't information, it's action? 

This episode, I'm getting into something that's been on my mind for a while: the claim that Caribbean remote work voices like Krishna Dewor, Priscilla McClure, and Oshido Christie are gatekeeping opportunities from the rest of us. 

Spoiler: they're not, and I'll walk you through what's actually happening instead.

In this episode:

• Why the "gatekeeping" label gets thrown at career creators everywhere, not just here
• What competing in a truly global remote job market actually looks like
• The nine months it took me to land my next role after sixteen years in an office
• Seven concrete moves to make this week if you're serious about landing remote work
• The one thing most people skip: actually asking for help

Head to theremoteislander.com for more tools to help you land your next remote role.
Also check out the Global Caribbeans job board and the recap of the Caribbean Remote Work Conference 2026

You can find all of our links here:
https://linktr.ee/theremoteislander

Links mentioned:
BairesDev
Keron Rose's Blog
EF SET 15-minute test

*Edit: Payoneer has stopped its referral program but you can sign up for an account here.

Ever wondered how to get to a point in your career where you can CHOOSE your next job? Krishna Dewor has the answer.

Krishna is a Client Support Concierge based in Kingston, Jamaica, with eight years of remote work under his belt. He was one of the amazing speakers at the first Caribbean Remote Work Conference in June, where thousands tuned in for his breakdown of what actually makes a resume work. 

In this episode, we get into it all: over-communication as a remote work superpower, why your resume needs to change for every single job you apply to, debunking "gate-keeping" and why AI and no-code tools like Zapier are becoming must-have skills, not nice-to-haves.

What we cover:

• How Krishna went from a hybrid role to fully remote, and why the commute was the final straw
• The real meaning of ATS and why your resume gets filtered before a human ever sees it
• Zendesk, Salesforce and the no-code tools worth learning even if you're not "technical"
• What to do to take your remote career to the next level - pick, choose and refuse jobs on your own terms

Listen to the full conversation and check out more resources at theremoteislander.com.

Guest: Krishna Dewor, Client Support Concierge, Kingston, Jamaica
Connect with Krishna on LinkedIn

You can find all of our links here:
https://linktr.ee/theremoteislander

Links mentioned:
BairesDev
Keron Rose's Blog
EF SET 15-minute test

*Edit: Payoneer has stopped its referral program but you can sign up for an account here.

What does it actually take to get hired for a remote job, straight from the person on the other side of the table making the hiring decisions?

This week I sit down with Tahirah Banks-Webster, founder and strategist from Anguilla who runs AlphaNorth Global and ShipSmart Logistics. Unlike most guests on the show, Tahirah isn't looking for remote work, she's the one doing the hiring, building and leading distributed teams across the Caribbean and the US. She pulls back the curtain on exactly what employers are really looking at when your application lands in front of them.

In this episode:

• Tahirah's three-part hiring process, and why LinkedIn's "good fit" score isn't the whole story
• The instant disqualifiers most candidates don't even know about
• Why trust is the real barrier to tech adoption in the Caribbean, and how to build it
• What actually makes a remote candidate stand out (hint: it's not your degree)
• The home workspace habits that signal you're ready for remote work

If you're serious about landing a remote job, this is the episode that shows you exactly what's happening on the other side of the screen. Head to theremoteislander.com for more.

You can find all of our links here:
https://linktr.ee/theremoteislander

Links mentioned:
BairesDev
Keron Rose's Blog
EF SET 15-minute test

*Edit: Payoneer has stopped its referral program but you can sign up for an account here.

The Caribbean has genuine remote work advantages: English fluency, cultural alignment with North America, strong technical education, so why isn't the opportunity converting at scale? 

In this episode, I break down the real, data backed reasons the Caribbean remote work gap exists, and it's not the reason most people think. From IMF brain drain figures to a LinkedIn presence problem that's bigger than anyone admits, this is a no fluff look at what's actually holding Caribbean professionals back, and what to do about it starting today.

In this episode you'll learn:

• Why the "just get a degree" advice is outdated for global hiring
• The truth about ATS systems and why 92% of recruiters aren't auto-rejecting your resume
• Why your location filter might be quietly killing your job search
• The staggering LinkedIn visibility gap facing Caribbean professionals
• What Latin America's remote work boom can teach (and warn) the Caribbean

Ready to stop guessing and start strategizing your remote career? Head to theremoteislander.com for more episodes, resources, and real talk on building a global career from home.

You can find all of our links here:
https://linktr.ee/theremoteislander

Links mentioned:
BairesDev
Keron Rose's Blog
EF SET 15-minute test

*Edit: Payoneer has stopped its referral program but you can sign up for an account here.

If you're earning money from a foreign employer and living in Jamaica, you have a tax obligation - and it's yours to manage, not your employer's. 

In this episode, I sit down with Colette Guthrie, a tax professional at PriceWaterhouseCoopers Jamaica, to break down exactly what Jamaican remote workers need to know about paying their taxes correctly.

We cover:

• How tax residency works and why it means you're taxed on your worldwide income
• The four statutory deductions every self-employed remote worker must account for
• How to set up your account with Tax Administration Jamaica (TAJ) and file as self-employed
• Deductible business expenses — including your internet and phone
• The biggest mistakes people make when filing (and how to avoid them)

Head to theremoteislander.com for the full Jamaican Remote Worker Tax Guide, a free resource to go alongside this episode.

Guest: Colette Guthrie — Tax Professional, PwC Jamaica 

LinkedIn: https://www.linkedin.com/in/colette-guthrie-adit-03558062/ 

Instagram: @thoughtstothewise 

Facebook: https://www.facebook.com/share/18ceCDK36F/

You can find all of our links here:
https://linktr.ee/theremoteislander

Links mentioned:
BairesDev
Keron Rose's Blog
EF SET 15-minute test

*Edit: Payoneer has stopped its referral program but you can sign up for an account here.

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 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/

You can find all of our links here:
https://linktr.ee/theremoteislander

Links mentioned:
BairesDev
Keron Rose's Blog
EF SET 15-minute test

*Edit: Payoneer has stopped its referral program but you can sign up for an account here.

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

Links mentioned:
BairesDev
Keron Rose's Blog
EF SET 15-minute test

*Edit: Payoneer has stopped its referral program but you can sign up for an account here.

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

Links mentioned:
BairesDev
Keron Rose's Blog
EF SET 15-minute test

*Edit: Payoneer has stopped its referral program but you can sign up for an account here.

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

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

Links mentioned:
BairesDev
Keron Rose's Blog
EF SET 15-minute test

*Edit: Payoneer has stopped its referral program but you can sign up for an account here.