Straight to the employer's own application — no middleman.
The posting explicitly names 'The Americas' as an allowed region, which includes the anglophone Caribbean. The timezone requirement '+2 /-6 UTC' encompasses UTC-4 and UTC-5 (the target user's timezone window). The role is fully remote with no physical presence requirement. English is the only language required. The employment path is employee, and no US work authorization language appears; the phrase 'as long as you're authorized to work where you live' respects local Caribbean work authorisation only.
“The Americas; Portugal; United Kingdom; Spain” Geographic scope — Americas / AMER / Western Hemisphere — includes the anglophone Caribbean.
“Stated location / restrictions: The Americas; Portugal; United Kingdom; Spain” Geographic scope — The Americas explicitly includes the anglophone Caribbean (Jamaica, Trinidad & Tobago, Guyana, Barbados, Bahamas, Belize, OECS islands).
“this role requires you to be based within +2 /-6 UTC” Timezone — The range +2 /-6 UTC includes UTC-4 and UTC-5, where the target user (Jamaica, UTC-5) falls within the window. 08:00–18:00 UTC-5 overlaps with 06:00–00:00 UTC (6 hours of overlap minimum).
“Fluent English language skills.” Language — Only English proficiency is required; no additional languages mandated.
“as long as work is timely, your team is supported, and you're authorized to work where you live, you can work from anywhere” Work authorization — Work authorization requirement is tied to the user's own country (Caribbean), not US/EU/UK. No sponsorship language appears; role is employee but no US visa sponsorship prohibition stated.
One platform, a whole world of opportunity
The best jobs have always clustered in a handful of the world's wealthiest cities. But talent is everywhere. Oyster set out to close that gap - building a global employment platform that lets companies hire, pay, and care for brilliant people anywhere.
We're proof that a high-performing culture doesn't need an office. Distributed across 60+ countries since 2020, we've built something the industry keeps noticing:
Ranked #10 of 250 on TIME and Statista's 2026 list of America's Top WorkTech Companies
Named one of America's Greatest Startup Workplaces 2026 by Newsweek
A G2 Spring 2026 Leader across Employer of Record, Global Employment, Multi-country Payroll, and HR Compliance
The only B Corp-certified global employment platform ~ independently verified since 2023
Two of those rankings measured our business impact from the outside. One measured how our own people feel about working here. They landed in the same place ~ because at Oyster, culture and performance aren't separate conversations. They're the same one.
And we're just getting started. If you want to do the best work of your career alongside people who care as much as you do, we'd love for you to apply.
Location: While this position is posted in a specific location, all of Oyster’s positions are fully remote and you can work from home. Forever. To create the best experience for our new hire, this role requires you to be based within +2 /-6 UTC.
As the Senior Manager, Product Design , you will lead, inspire, and scale a distributed team of Product Designers and UX Researchers. You will own the design vision for Oyster’s platform, ensuring our complex global employment workflows feel intuitive, seamless, AI-native, and deeply human.
A critical focus of this role will be pioneering our next-generation design workflows. You will champion the strategic adoption of AI within the design organization, optimizing how we research, prototype, and build, while guiding your team in architecting intuitive UI, Zero-UI, and agentic experiences for our customers.
AI-Augmented Design Ops: Drive the internal adoption of emerging AI and automated tooling within the design lifecycle (e.g., AI-assisted prototyping, automated UI generation, and LLM-driven research synthesis) to exponentially maximize team velocity .
Agentic & Data-Driven UX: Partner with Product and Engineering to define how AI elegantly enhances the Oyster user experience, translating complex global compliance, tax, and payroll data into proactive, multi-modal, and agentic workflows .
Our values guide the work we do, the decisions we make, and the culture that makes Oyster what it is. We make it happen—progress is our default setting. We drive change, we build and give trust, and we move as one united team.
Our mission is to create a more equal world of work: helping companies everywhere hire, pay, and care for talent anywhere. Everything we do ladders up to our mission. We embrace asynchronous, collaborative work and share how we operate in the Oyster Public HQ so other global teams can learn from us.
We embrace diverse perspectives and intentionally build our product and company with an inclusive, global mindset. We encourage you to apply, even if you don’t meet every criterion, and are committed to a trust-based, thriving environment.
Oyster is committed to ensuring equal opportunity of employment for qualified persons with disabilities and actively fosters an inclusive work environment. If you require reasonable accommodations throughout the recruiting process, please email jobs@oysterhr.com with the subject line: Interview Accommodations.
Our available positions are on our careers page. Our team will only contact you from an @ oysterhr.com email, and we will never ask for money as part of an interview process or job offer. If you receive a suspicious email about Oyster jobs or are directed to a site other than www.oysterhr.com/careers , please report it via our Compliance and Ethics Helpline .
Straight to the employer's own application — no middleman.
Tell us and we'll mark oyster as a company that has actually hired in the Caribbean. It's the most useful thing on this board and it only exists because people report it.
I got hired here →
