Manager, Customer Success (Americas)

Uncover; Northern (KY); Hybrid; USD 110,000 - 160,000; Full time

Benefits offered by this job

Work from anywhere

40 days off per year

Mental health support

Wellbeing allowance

Flexible parental leave

WFH stipend

Job summary

Oyster is transforming distributed work by enabling companies to hire talent anywhere. We’re seeking a hands-on, strategic Customer Success Manager to lead our AMER Dedicated CSM team: a group of 5 experienced CSMs serving top‑tier customers across the Americas.

You will own retention and revenue, coach and scale the team across time zones, collaborate with Sales, Product, and Ops, and drive AI-enabled workflows to improve outcomes and efficiency.

Qualifications

• 5+ years in customer-facing roles, with 2+ years in CS or account management.
• Experience managing a multi-country book of business and ARR.
• Strong communication and stakeholder management across levels.
• Comfort with data, analytics, and metrics to drive decisions.
• Familiarity with AI tools to improve customer outcomes.

Responsibilities

• Lead, mentor, and develop a team of 5 CSMs across West and East AMER.
• Drive capacity planning and portfolio balancing across the team.
• Own hiring for open roles and ensure sub-regional coverage matches the AMER customer base.
• Own retention and net revenue outcomes for the AMER dedicated-tier portfolio.
• Establish early-warning systems for at-risk accounts and escalate appropriately.
• Partner with Sales on expansion opportunities within dedicated accounts.
• Manage escalations with cross-functional teams to resolve issues.
• Translate customer feedback into actionable insights for Product, Ops, and GTM.
• Drive AI-powered playbooks and adoption within the CS function.
• Contribute to churn reviews with data-backed risk assessments and options.

Skills

Customer Success

People Management

Portfolio Management

Data Analytics

AI Tools

Cross-Functional Collaboration

Customer Obsession

Tools

Salesforce

Zendesk

Looker

Job description

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.

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.

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.

Key Responsibilities

• Team Leadership & Coaching – Lead, mentor, and develop a team of 5 CSMs across West and East AMER. 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.


• Drive capacity planning and portfolio balancing across the team, using effort scoring (FTEs, call volume, email volume, country complexity) to ensure equitable and sustainable workloads.


• Own hiring for open roles, including backfills and new headcount, ensuring the team's sub-regional coverage matches the AMER customer base.


• Customer Health, Retention & Expansion – Own the retention and net revenue outcomes for the AMER dedicated-tier portfolio, including churn/contraction prevention and expansion/upsell identification.


• Establish and enforce early-warning systems for at-risk accounts, ensuring CSMs are proactively flagging churn signals and engaging the right internal stakeholders before escalation.


• 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.


• Manage escalations effectively, working cross‑functionally with Operations, Product, Legal, and Pay teams to find prompt resolutions and close the loop with customers.


• Voice of the Customer & Cross-Functional Influence – Translate customer feedback, risks, and requirements into actionable insights for Product, Operations, and Go-to-Market teams.


• Drive accountability on gaps and failures with cross-functional partners, represent the customer impact clearly and push for resolution timelines.


• Contribute to the biweekly churn & contraction review with data-backed risk assessments and save strategies.


• AI Adoption & Operational Efficiency – 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.


• Drive AI literacy across the team and ensure every CSM is proficient in using AI tools for account research, meeting preparation, customer health analysis, and internal reporting.


• 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.

Core Requirements

• 5+ years in customer-facing roles, with at least 2 years in Customer Success or Account Management in a B2B SaaS environment.


• 2 years of people management experience, ideally leading a team across multiple time zones within the Americas.


• Experience managing a book of business with commercial accountability (retention, expansion, churn prevention).


• Exceptional interpersonal and communication skills, with the ability to influence cross-functionally at senior levels.


• Strong problem-solving and conflict resolution capabilities, and comfortable navigating ambiguity and internal complexity.


• Proven operating rhythm discipline: ability to keep routine deliverables on track while managing concurrent escalations.


• Comfort with data and analytics: able to interpret portfolio health metrics, ARR data, and engagement signals to make decisions.


• Familiarity with AI tools and a demonstrated willingness to adopt technology to improve team efficiency and customer outcomes.


• Customer-focused mindset with a genuine desire to help clients succeed.


• Ability to thrive in a fast-paced, scaling environment where processes are still being built.


• Detail-oriented with excellent organisational skills.


• Proactive: you see gaps and fill them before being asked.


• Curious about AI and technology: you actively explore how new tools can make your team better.

BONUS

• Experience in the global employment, HR technology, or EOR/PEO space.


• Familiarity with the complexities of multi-country employment (payroll, compliance, benefits).


• Experience with Salesforce, Zendesk, and data/BI tools (Looker).


• Previous experience building or scaling a CS function from scratch.

You'll also need

• A reliable home internet connection and fluency in both written and spoken English.

How we work together at Oyster

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.

How YOU work

• Work from anywhere: Oyster has no borders or HQ. As long as work is timely, your team is supported, and you're authorized to work where you live, you can work from anywhere.


• Paid time off: Enjoy 40 days off per year (including holidays and vacation), or more if required by your country.


• Mental health support: Access Plumm, our mental well‑being service.


• Wellbeing allowance: Each month, receive a wellbeing allowance in your ThanksBen wallet to spend on a wide range of options.


• Flexible parental leave: All new parents are eligible for at least three months’ paid leave, with job protection for up to 12 months or as required locally.


• WFH stipend: Receive a stipend for your laptop and home office equipment to get you set up quickly.

We 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 [e-mail] 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.