Head of Customer Success

Remote, United States

Job Details

Location: United States

Workplace: Remote

Employment Type: Full-time

Experience: 7+ years in Customer Success or Customer Operations, including 3+ years managing multiple functions

Core Areas: Customer Retention, Gross Revenue Retention (GRR), Net Revenue Retention (NRR), Customer Health Scoring, Customer Onboarding & Implementation, Account Expansion, Customer Support Operations, Customer Success Leadership

Compensation: $155,000–$190,000 annually

About the Role

This opportunity is for an experienced Head of Customer Success to lead customer success, implementation, and support operations for a growing healthcare technology organization. The position owns the customer lifecycle from signed contract through onboarding, adoption, expansion, and renewal, with direct accountability for gross revenue retention (GRR), net revenue retention (NRR), churn reduction, and customer experience. The role focuses on building a measurable, scalable customer success organization supporting hundreds of accounts.

The Head of Customer Success will develop customer health scoring, account segmentation, retention analytics, and customer coverage models while improving implementation time to value and support efficiency. The position requires hands-on CRM and customer data expertise, experience managing cross-functional customer-facing teams, and the ability to translate customer behavior into actionable product insights. The role reports directly to the CEO and oversees customer success, implementation, and support leaders and specialists.

What You'll Do

• Own gross revenue retention (GRR) and net revenue retention (NRR), establishing measurable strategies to reduce customer churn and protect recurring revenue.
• Analyze customer churn across practice size, electronic health record (EHR) systems, product lines, onboarding cohorts, and customer tenure to identify retention risks and their underlying causes.
• Develop and implement customer health scoring models that identify at-risk accounts and enable proactive retention management.
• Build scalable account segmentation and coverage models that support hundreds of small and midsize business (SMB) customers with relatively low annual contract values (ACVs).
• Track retention performance, evaluate the impact of customer success initiatives, and explain changes in GRR using measurable customer and operational data.

• Build a structured customer expansion strategy that increases adoption of additional products across existing accounts.
• Identify product adoption sequences, expansion opportunities, and appropriate engagement timing throughout the customer lifecycle.
• Establish clear ownership of expansion activities across customer-facing teams.
• Partner with Sales and Account Executives (AEs) on handoffs and coordination for larger expansion opportunities.
• Protect existing net revenue expansion performance while developing more consistent and repeatable growth processes.

• Oversee customer implementation and onboarding operations in partnership with the Director of Implementation.
• Establish measurable time-to-value targets for different customer segments and monitor implementation performance against those targets.
• Evaluate how onboarding quality, implementation decisions, and early customer experiences affect first-year retention.
• Develop baseline implementation metrics and use customer outcomes to prioritize improvements in onboarding processes.
• Coordinate changes to implementation workflows and customer coverage strategies to improve adoption, retention, and time to value.

• Lead customer support operations with accountability for service responsiveness, support quality, and operational efficiency.
• Develop scalable support processes that allow customer volume to grow without proportional increases in support headcount.
• Implement support deflection strategies using customer documentation, in-product guidance, and AI-assisted support triage.
• Evaluate support workflows and identify opportunities to improve issue resolution and reduce repetitive customer support requests.

• Define and document the complete customer journey, including contract handoff, implementation, onboarding, ongoing customer success, expansion, and renewal.
• Assign clear ownership and accountability for each stage of the customer lifecycle and every transition between teams.
• Align customer success, implementation, and support operations to deliver a consistent and coordinated customer experience.
• Develop customer lifecycle metrics and reporting processes that provide leadership with visibility into account health, retention risks, and operational performance.

• Establish a consistent process for collecting, analyzing, and communicating customer behavior and product usage insights to Product teams.
• Translate observed customer activity into actionable feedback that informs product development and customer experience improvements.
• Provide customer references, performance metrics, and supporting information for analyst relations initiatives and customer case studies.
• Maintain a predictable cadence for sharing customer insights with Product and other internal stakeholders.

• Lead and develop a cross-functional organization that includes a Director of Implementation, Customer Success Lead, Implementation Specialist, and Support Specialist.
• Assess team capabilities, organizational structure, staffing requirements, and management processes to support significant growth in the customer base.
• Coach and develop customer-facing employees while making organizational and staffing decisions based on business needs.
• Plan hiring and team expansion as the customer portfolio grows.

• First 90 Days: Develop account-level understanding of the customer portfolio, quantify the main drivers of churn, evaluate team structure and staffing needs, and identify three primary operating metrics.
• First 6 Months: Implement customer health scoring trusted by Sales and leadership, document the customer journey with clear ownership, establish time-to-value baselines by segment, and introduce initial onboarding or coverage improvements with measurable GRR hypotheses.
• First 12 Months: Demonstrate measurable improvement in GRR while maintaining or improving NRR, establish a clearly structured and growing customer success organization, and deliver customer insights to Product on a consistent schedule.

Qualifications

Required Experience

• 7+ years of professional experience in Customer Success or Customer Operations.
• 3+ years of management experience overseeing more than one customer-facing function.
• Demonstrated ownership of gross revenue retention (GRR), including a measurable record of improving retention performance and the ability to explain the strategies and operational changes responsible for those results.
• Direct experience leading or closely partnering with customer implementation teams, with a practical understanding of how onboarding quality influences long-term customer retention.
• Experience managing customer success operations at SMB scale, including portfolios of hundreds of accounts with relatively small annual contract values.
• Proven experience developing employees, evaluating organizational structures, and making staffing and management decisions.

Required Skills

• Strong expertise in customer retention management, churn analysis, GRR, NRR, and customer lifecycle optimization.
• Ability to analyze retention performance across customer segments, product lines, onboarding cohorts, account tenure, and EHR systems.
• Hands-on proficiency with CRM systems and customer data analysis, including the ability to independently build an initial customer health scoring model.
• Practical knowledge of customer segmentation and account coverage models designed for large portfolios of SMB accounts.
• Ability to establish customer onboarding and implementation performance metrics, including time-to-value benchmarks and first-year retention indicators.
• Experience coordinating customer success, implementation, and support activities across multiple teams and customer lifecycle stages.
• Ability to develop customer-facing teams, evaluate staffing requirements, and support organizational growth.

Preferred Qualifications

• Experience in healthcare or health technology, particularly medical practice workflows, electronic health record (EHR) integrations, and HIPAA requirements.
• Experience supporting AI-enabled software products and managing customer expectations around AI functionality.
• Familiarity with customer support technology, support automation, and deflection strategies at scale.
• Experience carrying an account expansion quota or managing employees responsible for expansion revenue.
• Hands-on experience with HubSpot.

Benefits

• Health insurance coverage.
• Dental insurance coverage.
• Vision insurance coverage.
• Unlimited paid time off (PTO).
• Regular company offsites.