How we9re 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 that9s fairer than a rolling 49maybe never49 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, we9re transforming distributed work by enabling companies everywhere to hire talent anywhere through our platform and suite of global employment solutions. We9re 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 Oyster9s highest-value customers across the Americas.

This role sits at the intersection of people leadership, customer strategy, and operational excellence. You9ll own the health, retention, and expansion outcomes for Oyster9s 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 Oyster9s 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 team9s 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 Oyster9s 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
• [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

You9ll also need

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