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Head of Customer Success

Job in San Antonio, Bexar County, Texas, 78201, USA
Listing for: Jobgether
Full Time position Listed on 2026-11-15
Job specializations:
Salary/Wage Range or Industry Benchmark: 194000 - 291000 USD Yearly USD 194000.00 291000.00 YEAR

Job Description & How to Apply Below

This position is listed on behalf of a partner company, which manages all applications and next steps. Our partner is looking for a Head of Customer Success based in the United States.

The Head of Customer Success will provide strategic leadership for a growing Customer Success organization serving Enterprise, Mid-Market, and SMB customers. Reporting to the VP of Customer Success, this high-impact role will shape the customer experience and drive adoption, value realization, stakeholder alignment, and retention. You will lead a team of Directors, Managers, and Customer Success Managers while developing scalable, outcomes-focused customer engagement strategies.

Working closely with Sales, Product, Marketing, Operations, and Support, you will strengthen cross-functional collaboration and improve the customer lifecycle. You will also guide the evolution toward a trusted-advisor model, supported by data-driven processes, technology, and customer insights. This is an opportunity to influence business performance through stronger customer relationships, measurable value, and sustainable retention.

Accountabilities
  • Own the overall strategy, execution, and performance of the Customer Success organization, ensuring alignment with business objectives and customer outcomes.
  • Lead Customer Success teams supporting Enterprise, Mid-Market, and SMB segments, developing effective leadership structures and consistent career paths in partnership with the People team.
  • Design segmented customer lifecycle strategies that balance high-touch engagement with scalable digital adoption and enablement approaches.
  • Partner with Sales to identify and support upsell and cross-sell opportunities while contributing to revenue and retention targets.
  • Collaborate with Operations and IT to optimize Gainsight configuration, customer health scoring, adoption metrics, reporting, and success plays.
  • Work with Marketing to develop customer communications, collateral, and advocacy initiatives.
  • Partner with Product Management and Product Marketing to support successful customer migrations from legacy products to next-generation solutions.
  • Build and maintain a comprehensive Voice of the Customer program, including Net Promoter Score (NPS) and customer satisfaction surveys.
  • Establish regular feedback and collaboration practices with Product, Services, and Support teams to identify customer needs and opportunities for improvement and innovation.
  • Develop repeatable processes and templates for onboarding, new-feature adoption, quarterly business reviews, and account expansion.
  • Own executive dashboards and reporting on renewal forecasts, churn risks, retention performance, and win/loss analysis.
  • Engage directly with customers when needed to resolve significant satisfaction issues and strengthen relationships.
  • Meet and exceed quarterly goals related to customer retention, revenue retention, renewals, and customer satisfaction.
Requirements
  • 15+ years of experience in Customer Success leadership, managing both Enterprise and scaled Customer Success functions.
  • 10+ years of people leadership experience, including leading Customer Success or Account Management teams.
  • Strong understanding of SaaS business models, industry performance metrics, and customer lifecycle management best practices.
  • Proficiency with Gainsight and experience using customer success technology to manage adoption, customer health, and retention.
  • Experience with business planning in transformation environments, including territory assignments, organizational planning, and performance reporting.
  • Strong analytical capabilities, with the ability to interpret data and communicate meaningful business insights to different audiences.
  • Proven ability to engage senior stakeholders and present…
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