Manager, Scaled Customer Success

Jobtailor; New York (NY); Hybrid; USD 180,000 - 230,000; Full time

Job summary

Jobtailor is seeking a Senior Leader to guide a team of 6+ Scaled Customer Success Managers across the United States and the United Kingdom. You will own the digital CS strategy, driving engagement, product adoption, and retention across emerging and mid-market segments.

Collaborating with Product, RevOps, and Enablement, you will design automated, tech-touch engagement solutions and foster a data-driven culture.

Qualifications

• 5+ years of Customer Success or Account Management experience in a SaaS organization
• 2+ years in people management or team lead capacity
• Experience with scaled or digital CS motions across segments (emerging, mid-market, Enterprise)
• Familiarity with CS platforms; Planhat preferred; Gainsight, Vitally or ChurnZero

Responsibilities

• Lead, coach, and develop a team of 6+ Scaled CSMs across the U.S. and U.K.
• Own the strategy and execution of digital customer success programs to drive engagement, adoption, and retention
• Partner with Product, RevOps, and Enablement to design, test, and iterate on automated engagement solutions
• Champion a data-driven culture using signals and insights to evolve programs
• Support renewals and expansions with commercial confidence and consistency
• Manage and report retention metrics, renewal forecasting, and customer health for a $22M+ ARR portfolio
• Influence tooling, process, and product roadmap decisions for the scaled segment

Skills

Team Leadership

Data-Driven Decision Making

Strategic Thinking

Cross-Functional Influence

Tools

Planhat

Gainsight

Vitally

ChurnZero

Job description

• Lead, coach, and develop a team of 6+ Scaled CSMs across the U.S. and U.K., each managing a high-volume book ranging from 100-400 accounts
• Own the strategy and execution of digital customer success programs designed to drive engagement, product adoption, and retention across the emerging and mid-market segments
• Partner with Product, RevOps, and Customer Enablement to design, test, and iterate on automated and tech-touch engagement solutions
• Champion a data-driven, hypothesis-testing culture — using signals and insights to continuously evolve your programs based on what's working
• Support and coach your team through renewal and expansion conversations, ensuring commercial confidence and consistency across the book
• Manage and report on key retention metrics, renewal forecasting, and customer health across a $22M+ ARR portfolio
• Serve as a key stakeholder and voice for the scaled segment internally, influencing tooling, process, and product roadmap decisions

Requirements

• 5+ years of Customer Success or Account Management experience within a SaaS organization, with at least 2 years in a people management or team lead capacity
• Proven track record leading scaled or digital CS motions, managing high-volume books of business across emerging, mid-market and Enterprise segments.
• Hands-on experience with Customer Success Platforms — Planhat strongly preferred; Gainsight, Vitally, or ChurnZero
• Familiarity with AI and automation tools and a genuine interest in applying them to improve customer engagement at scale
• Technically curious — comfortable constructing basic programs and automations, and skilled at identifying opportunities, scoping requirements, and managing cross-functional stakeholders to drive rapid deployment of more complex solutions
• Commercially sharp — able to guide your team through renewal negotiations and expansion conversations with confidence and empathy
• A natural experimenter: you love forming hypotheses, testing them, and letting data drive your decisions
• Strong communicator and influencer across internal functions — you know how to align Product, RevOps, and Enablement teams around a shared vision
• History of thriving in fast-moving, high-growth environments where the roadmap is still being written.

Core Competencies

Demonstrates expertise in leading and developing Customer Success teams, driving engagement and retention through data-driven strategies and automated solutions. Proficient in managing high-volume accounts within SaaS environments, with a strong focus on collaboration and communication across cross-functional teams.

Highest-signal resume keywords

• Customer Success Management
• Team Leadership
• Data-Driven Decision Making
• Customer Success Platforms
• SaaS Experience

ATS Optimization Keywords

Hard Skills

• Account Management
• Digital Customer Success Programs
• Renewal Forecasting
• Customer Health Metrics
• Automation Tools
• Program Construction
• Hypothesis Testing
• Engagement Solutions

Soft Skills

• Strong Communication
• Influencing Skills
• Empathy in Negotiations
• Coaching and Development

Industry Keywords

• SaaS
• Emerging Market
• Mid-Market
• Enterprise Segment
• High-Growth Environments

Tools & Technologies

• Planhat
• Gainsight
• Vitally
• ChurnZero