Head of Customer Success

Head of Customer SuccessLocation: Palm Beach, FL (Primarily Onsite with Hybrid Flexibility)Employment Type: Full-Time, Contract-to-Hire, or Fractional Leadership EngagementAbout the OpportunityWe are seeking an experienced and strategic Head of Customer Success to lead customer retention, engagement, and revenue growth across an established client portfolio. This senior leadership position is ideal for a customer-focused executive who combines strong relationship management skills with a data-driven approach to business performance.The successful candidate will take ownership of an existing portfolio of approximately 65 active clients, developing scalable strategies that improve customer outcomes, increase retention, reduce churn, and identify opportunities for account expansion. This role requires someone who can operate at both the executive and operational levels, building customer success processes while maintaining direct involvement with key client relationships.Key ResponsibilitiesCustomer Retention & GrowthOwn and improve customer retention, engagement, and recurring revenue performance.Develop strategies to increase Gross Revenue Retention (GRR) and recurring revenue growth.Reduce customer churn through proactive engagement and risk mitigation efforts.Identify opportunities for upselling, cross-selling, and account expansion.Establish customer health metrics and early-warning indicators for at-risk accounts.Create customer journey frameworks that drive long-term success and loyalty.Customer Success LeadershipBuild and implement a scalable customer success operating model.Develop processes, playbooks, and best practices to support client engagement and retention.Serve as an executive partner to key customers, ensuring measurable business value is delivered.Create accountability and visibility around customer success performance.Collaborate with leadership to align customer success initiatives with business objectives.Metrics, Reporting & AnalyticsDesign and manage dashboards, reporting systems, and KPIs related to customer success.Analyze customer data and trends to identify opportunities for improvement and growth.Track and report on retention, adoption, expansion revenue, engagement, and customer health.Use data-driven insights to influence strategic decisions and customer initiatives.Cross-Functional CollaborationPartner closely with sales, marketing, operations, and executive leadership teams.Ensure a seamless customer experience from onboarding through renewal and expansion.Provide customer feedback and market insights to support product and business strategy.