Head of Customer Success

Payscale

. Own the overall strategy, execution, and results of the Customer Success organization .

Posted 11/12/2026full-timeRemote • United StatesLead💰 $194,000 - $291,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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

Demonstrates extensive expertise in Customer Success management, with a focus on leading teams across various segments and implementing strategies for customer engagement and satisfaction. Proficient in utilizing Gainsight for managing customer health metrics and driving operational excellence.

Highest-signal resume keywords

Customer Success ManagementGainsight ProficiencySaaS Business Model KnowledgeAnalytical SkillsPeople Leadership

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 Lifecycle ManagementBusiness PlanningTerritory AssignmentsReportingCustomer Health MetricsNPS Program ManagementFeature Adoption ProcessesOnboarding StrategiesQuarterly Business Reviews (QBRs)Renewal Forecasting

Soft Skills

Storytelling with NumbersStakeholder EngagementPresentation SkillsProblem ResolutionCollaboration

Tools & Technologies

GainsightDigital Adoption ToolsCustomer Communication PlatformsCollaboration SoftwareCustomer Feedback Systems

Industry Keywords

Customer SuccessEnterprise SegmentMid-Market SegmentSMB SegmentCustomer SatisfactionChurn Risk ManagementUpsell OpportunitiesCross-Sell OpportunitiesVoice-of-the-Customer ProgramsCustomer Advocacy

About the role

Key responsibilities & impact

Own the overall strategy, execution, and results of the Customer Success organization
Lead Customer Success teams across Enterprise, Mid-Market, and SMB segments
Shape the customer experience and operationalize an outcomes-oriented, trusted-advisor approach
Partner with the People team on job titles, levels, and career paths
Develop segmented lifecycle-management strategies for high-touch and scale segments
Partner with Operations and Customer Education on digital adoption and enablement for scale segments
Partner with Sales on upsell and cross-sell opportunities
Ensure Gainsight is configured and managed for Customer Success needs
Partner with Marketing on collateral, customer communications, and advocacy programs
Support migrations from legacy products to next-generation solutions
Create and maintain a voice-of-the-customer program, including NPS and customer satisfaction surveys
Establish cross-functional cadences for customer feedback and innovation
Develop repeatable processes and templates for feature adoption, onboarding, QBRs, and expansions
Manage customer health scores, adoption metrics, and success plays in Gainsight
Own executive dashboards for renewal forecasts, churn risk, and win/loss analysis
Engage with customers to resolve outstanding satisfaction issues
Meet and exceed quarterly customer and revenue retention targets
Report to the VP of Customer Success

Requirements

What you’ll need

15+ years in Customer Success management leading both Enterprise and Scaled CS functions
10+ years as a people leader running Customer Success or account management teams
Knowledge and experience of the SaaS business model, industry metrics, and customer lifecycle management best practices
Proficiency in Gainsight
Experience with business planning during transformations, territory assignments, and reporting
Strong analytical skills and ability to tell stories with numbers
Ability to work with senior stakeholders and present to senior executive audiences
High-speed internet with a minimum speed of 100 Mbps if working from home
Dedicated workspace with reliable Wi-Fi signal
Device for multifactor authentication (MFA/2FA)
Must be legally authorized to work in the United States; sponsorship requirements are addressed in the application

Benefits

Comp & perks

Annual corporate bonus eligibility
Flexible paid time off
14 paid company holidays, including 2 floating holidays
Medical, dental, life, vision, and disability insurance covered up to 100% by Payscale
Unlimited infertility coverage through medical plans
Supplemental health benefits for employees and families
401(k) retirement program with fully vested immediate company match
16 weeks of paid parental leave for birthing and non-birthing parents
Health Savings Account options and company contributions
Flexible Spending Account options
Annual remote work stipend for wellness or home office equipment
Continued learning and development opportunities
Executive leadership exposure through AMAs
Employee Resource Groups
Company-sponsored volunteer hours
Flexible remote-first work from home, company-paid coworking spaces, or a combination
In-person company events usually a few times per year