Customer Success Manager

About the Role

Oyster is 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.

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.

• 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.

• 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.

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