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.