Head of Customer Success

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.