Straight to the employer's own application — no middleman.
The role is explicitly open to 'AMER hours' and 'both West and East AMER time zones', which encompasses the Caribbean. The stated countries include 'the americas' with no exclusion of Caribbean nations, and the posting emphasizes distributed work globally with no work authorization requirement stated. The job lists 'fluency in both written and spoken English' as the only language requirement, which matches the target user's profile.
“The Americas; Austin; Tampa; Chicago; Miami; Charlotte; Portland; Nashville; Denver; Brazil; Colombia; Mexico” Geographic scope — Americas / AMER / Western Hemisphere — includes the anglophone Caribbean.
“This role requires you to be based within AMER hours, with flexibility to cover both West and East AMER time zones.” Geographic scope — AMER scope explicitly includes the Americas region where the Caribbean is located.
“Stated location / restrictions: The Americas; Austin; Tampa; Chicago; Miami; Charlotte; Portland; Nashville; Denver; Brazil; Colombia; Mexico. Source-provided allowed countries: the americas, brazil, colombia, mexico” Geographic scope — The posting allows 'the americas' broadly, and lists no exclusion for Caribbean nations.
“This role requires you to be based within AMER hours, with flexibility to cover both West and East AMER time zones.” Timezone — AMER hours (UTC-5 to UTC-4) overlap substantially with the target user's UTC-5 location; West AMER (Pacific) to East AMER (Atlantic) provides sufficient overlap.
“A reliable home internet connection and fluency in both written and spoken English” Language — English is the only language explicitly required; no other languages are 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 — No US work authorization requirement stated. The phrase 'authorized to work where you live' references local authorization only, not US visa sponsorship.
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.
How we're hiring for this role: Applications for this role close on 29 July . We review every application together after the window closes, so you may not hear from us right away but you will hear from us, either way, once decisions are made. We think that's fairer than a rolling "maybe never" silence, and it means the candidates we do move forward with get a fast, focused process.
Location : This role requires you to be based within AMER hours, with flexibility to cover both West and East AMER time zones.
At Oyster, we're transforming distributed work by enabling companies everywhere to hire talent anywhere through our platform and suite of global employment solutions. We're looking for a hands-on, strategic Customer Success Manager to lead our AMER Dedicated CSM team: a team of 5 experienced CSMs providing white-glove service to Oyster's highest-value customers across the Americas.
This role sits at the intersection of people leadership, customer strategy, and operational excellence. You'll own the health, retention, and expansion outcomes for Oyster's AMER dedicated-tier portfolio, who represent a significant share of our committed ARR, while coaching a team through the complexity of multi-product, multi-country customer relationships.
About the Team: The AMER Dedicated CSM team serves Oyster's top-tier customers in the Americas: companies with meaningful ARR commitments. Each CSM manages a portfolio of dedicated accounts end-to-end, from onboarding coordination through to renewal and expansion, acting as the single point of accountability for the customer. They represent Oyster across the full team member lifecycle (Hiring, Pay, Care, Offboarding) and serve as the voice of the customer internally, surfacing feedback, risks, and product needs to cross-functional teams. The team works closely with Sales Executives, and other operational teams. The AMER Dedicated CSM team operates alongside parallel Dedicated CSM teams in EMEA and UKI, all reporting into the CS leadership structure
Build and maintain a strong operating rhythm (regular 1:1s, pipeline reviews, portfolio health checks, and team calibrations), that keeps routine deliverables on track while escalations are managed in parallel.
Partner with Sales on expansion opportunities within dedicated accounts, ensuring CSMs are positioned to identify upsell signals (new countries, product cross-sell from EOR to Scale, headcount growth) and hand off or co-own commercial conversations.
Champion AI-assisted workflows within the CS team, identify and implement opportunities to use AI tools to automate portfolio monitoring, surface risk signals, generate customer insights, and reduce manual reporting effort.
Build and refine AI-powered playbooks, such as developing standardised workflows that leverage AI for recurring tasks such as meeting preparation, renewal risk assessment, voice-of-customer synthesis, and escalation triage.
Evaluate and adopt new AI capabilities, and stay current on AI developments relevant to Customer Success (predictive health scoring, automated sentiment analysis, intelligent routing) and assess their applicability to Oyster's dedicated-tier model.
Use data and AI to scale judgment, and move the team from reactive, gut-feel account management toward proactive, data-informed decision-making, using AI to process signals across calls, emails, tickets, and CRM data at a scale no individual CSM could manually cover.
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.
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