Head of Customer Success

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 effectively to executive-level audiences.

• Excellent leadership, communication, collaboration, and strategic decision-making skills.

• Ability to drive organizational change and establish scalable processes while maintaining a customer-first approach.

Benefits:

• Compensation: Annual base salary range of $194,000–$291,000, plus eligibility for a corporate bonus and a 25% CBP component as listed.

• Remote-first working model, with the flexibility to work from home or company-paid coworking spaces.

• Flexible paid time off.

• 14 paid company holidays, including two floating holidays.

• Comprehensive medical, dental, vision, life, and disability insurance, with coverage paid up to 100% by the employer.

• Infertility coverage through medical plans and additional supplemental health benefits for employees and their families.

• 401(k) retirement plan with an immediately vested company match.

• 16 weeks of paid parental leave for birthing and non-birthing parents.

• Health Savings Account (HSA) options with company contributions and Flexible Spending Account (FSA) options.

• Annual remote-work stipend for wellness or home-office equipment.

• Ongoing learning and professional development opportunities.

• Regular company-wide meetings and opportunities to engage with executive leadership.

• Continuous feedback and career development programs.

• Employee Resource Groups and company-sponsored volunteer hours.

• Occasional in-person team gatherings, generally limited to a few times per year.