I cracked the code to landing a remote marketing job with a US startup — with no degree. Here's my advice for Caribbean job seekers.
This story is part of a series of as-told-to essays based on conversations with mid-career and senior professionals across multiple sectors. It has been edited for length and clarity.
ShortlistHR is building a collection of career stories from Caribbean professionals who've successfully transitioned to remote work with global companies. If you've navigated this path and want to share your experience — from the job search to salary negotiations to work culture adjustments — email kerry@shortlisthr.com. I’m particularly interested in concrete details about your journey and practical advice for others looking to make similar moves.
What we cover in this newsletter
How a portfolio-first approach trumps traditional credentials
How to build a strategic remote job search that works
Essential skills for remote success
The reality shock of US remote startup culture
The big picture: After running a marketing and communications consultancy in Trinidad for 12 years, I pursued a dream I’d nurtured for a long time: landing a job at a US company. I thought I knew what I was getting into when I finally landed a role as a content marketing manager — without US work authorisation, a degree, or having to relocate. I was wrong. The experience taught me that working remotely for a high-growth company demands more than just talent; it requires a complete reset of how you think about your job search, and about work itself — especially if you’ve spent all of your working life in the Caribbean.
Why it matters: The rise of remote work has Caribbean professionals eyeing opportunities with US companies.
But here's the truth — unless you understand certain realities upfront, you're likely making critical mistakes in your job search. And even if you land a role, showing up unprepared could cut your tenure short.
This is especially crucial when targeting high-growth, VC-backed startups. First lesson: Know where you’re applying. A startup is not your typical company. They're scrappy, fast-moving operations where you're expected to figure things out on the fly while delivering results.
It means asking yourself questions you might have never considered. Do you want a job that challenges you to grow (in a healthy way) or do you want to get on a hamster wheel and feel like you’re never getting off? You need to know the trade-offs going in, because trust me, your most important career decisions all come with trade-offs.
For me, I wanted to work for a technology-forward company that 1) prioritised skills and 2) was committed to producing meaningful work. Based on nothing more than my own work philosophy, I believed that this would have been far more rewarding professionally than Trinidad's corporate landscape, which I think is stuck in traditional hierarchies and paper credentials.
So in late 2023, after growing increasingly frustrated with the consulting experience in Trinidad, I spotted an opportunity to apply for the content marketing manager role at Wander. Here’s what I learned: