Manager, Customer Success – Americas

This is a fully remote position, open to applicants in United States.

📋 Description

• Lead, mentor, and develop a team of five Customer Success Managers (CSMs) across the West and East AMER regions.

• Establish and uphold a robust operational rhythm (including regular one-on-ones, pipeline reviews, portfolio health assessments, and team calibrations), ensuring routine deliverables are maintained while managing escalations concurrently.

• Facilitate capacity planning and portfolio balancing within the team, utilizing effort scoring (FTEs, call volume, email volume, country complexity) to guarantee equitable and sustainable workloads.

• Oversee the hiring process for open positions, encompassing backfills and new headcount, to ensure that the team's sub-regional coverage aligns with the AMER customer demographic.

• Take ownership of retention and net revenue outcomes for the dedicated-tier portfolio in AMER, focusing on preventing churn/contraction and identifying opportunities for expansion/upsell.

• Develop and implement early-warning systems for accounts at risk, ensuring CSMs proactively identify churn signals and engage appropriate internal stakeholders prior to escalation.

• Collaborate with Sales on expansion opportunities within dedicated accounts, empowering CSMs to recognize upsell signals (new countries, product cross-sell from EOR to Scale, headcount growth) and facilitate or co-manage commercial discussions.

• Effectively manage escalations, partnering cross-functionally with Operations, Product, Legal, and Pay teams to find swift resolutions and communicate outcomes with customers.

• Convert customer feedback, risks, and requirements into actionable insights for Product, Operations, and Go-to-Market teams.

• Foster accountability for gaps and failures among cross-functional partners, clearly representing customer impact and advocating for resolution timelines.

• Participate in the biweekly churn and contraction review, providing data-driven risk assessments and strategies for retention.

• Advocate for AI-assisted workflows within the Customer Success team, identifying and implementing opportunities to leverage AI tools for automating portfolio monitoring, surfacing risk signals, generating customer insights, and minimizing manual reporting workloads.

• Promote AI proficiency across the team, ensuring that every CSM is adept at utilizing AI tools for account research, meeting preparation, customer health analysis, and internal reporting.

• Develop and enhance AI-powered playbooks, including standardized workflows that utilize AI for recurring tasks such as meeting preparation, renewal risk assessment, voice-of-customer synthesis, and escalation triage.

• Assess and integrate new AI capabilities while staying updated on AI advancements pertinent to Customer Success (predictive health scoring, automated sentiment analysis, intelligent routing) and evaluating their relevance to Oyster's dedicated-tier model.

• Utilize data and AI to enhance judgment, transitioning the team from reactive, intuition-based account management to proactive, data-informed decision-making by employing AI to process signals across calls, emails, tickets, and CRM data that no individual CSM could manually oversee.

⛳️ Requirements

• Over 5 years of experience in customer-facing roles, with a minimum of 2 years in Customer Success or Account Management within a B2B SaaS context.

• At least 2 years of people management experience, preferably leading a team across multiple time zones in the Americas.

• Experience managing a portfolio with commercial accountability (including retention, expansion, and churn prevention).

• Exceptional interpersonal and communication abilities, capable of influencing at senior cross-functional levels.

• Strong problem-solving and conflict resolution skills, comfortable navigating ambiguity and internal complexities.

• Proven discipline in maintaining operational rhythms: ability to keep routine deliverables on schedule while managing concurrent escalations.

• Proficiency with data and analytics: capable of interpreting portfolio health metrics, ARR data, and engagement signals to inform decisions.

• Familiarity with AI tools and a demonstrated openness to adopting technology to enhance team efficiency and customer outcomes.

• Customer-centric mindset with a sincere commitment to supporting client success.

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

• Detail-oriented with outstanding organizational capabilities.

• Proactive in identifying and addressing gaps before being asked.

• Inquisitive about AI and technology: actively exploring how new tools can enhance team performance.

• [BONUS]: Experience in global employment, HR technology, or EOR/PEO sectors.

• [BONUS]: Knowledge of the complexities surrounding multi-country employment (payroll, compliance, benefits).

• [BONUS]: Experience with Salesforce, Zendesk, and data/BI tools (Looker).

• [BONUS]: Prior experience in building or scaling a Customer Success function from the ground up.

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

🏝️ Benefits

• Paid time off: Enjoy 40 days of leave per year (including holidays and vacation), with the possibility of additional days based on your location.

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

• Wellbeing allowance: Receive a monthly allowance in your ThanksBen wallet for a variety of wellbeing options; check the benefits catalogue for suggestions.

• Flexible parental leave: New parents are eligible for at least three months of paid leave, with job protection for up to 12 months or as required by local regulations.

• Work-from-home stipend: Receive a stipend for your laptop and home office setup to ensure you can get started quickly.