Manager, Customer Success – Americas

Oyster

Manager of Customer Success leading a team across the Americas in a remote setting to support Oyster's global employment platform. Drive retention and expansion for high-value customers across the region.

Posted 7/20/2026full-timeRemote • 🇺🇸 United StatesMid-LevelSenior💰 $85,000 - $110,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates strong leadership in managing a Customer Success team, with a focus on retention, expansion, and leveraging AI tools to enhance operational efficiency. Proven ability to analyze data for informed decision-making and maintain effective communication across cross-functional teams.

Highest-signal resume keywords

Customer Success ManagementPeople ManagementData AnalysisAI Tool AdoptionB2B SaaS Experience

ATS Keywords

Tailor your resume

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills

Customer RetentionChurn PreventionPortfolio ManagementCommercial AccountabilityData InterpretationAI Workflow ImplementationRisk AssessmentEscalation ManagementOperational DisciplineMulti-Country Employment Knowledge

Soft Skills

Interpersonal SkillsCommunication SkillsProblem-SolvingProactivityOrganizational Skills

Tools & Technologies

SalesforceZendeskData/BI ToolsAI ToolsCRM Systems

Industry Keywords

B2B SaaSCustomer SuccessAccount ManagementGlobal EmploymentHR Technology

Tech Stack

Tools & technologies

About the role

Key responsibilities & impact

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.
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.
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.
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.

Requirements

What you’ll need

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
[BONUS]: Familiarity with the complexities of multi-country employment (payroll, compliance, benefits)
[BONUS]: Experience with Salesforce, Zendesk, and data/BI tools (Looker)
[BONUS]: Previous experience building or scaling a CS function from scratch
A reliable home internet connection and fluency in both written and spoken English.

Benefits

Comp & perks

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. Spend it on a wide range of options; see the benefits catalogue for ideas.
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.