Vice President of Customer Success, Cents

• 10+ years of experience
• You’ve built or scaled Customer Success and onboarding organizations before
• You’ve designed segmentation, health scoring, and NRR models from the ground up
• You’re comfortable operating at both strategic and operational depth
• You know the difference between activity and impact
• You bring structure without bureaucracy
• You respect what’s working—and know when it’s time to evolve it

Desirable

• Customer Success at our company is working—and working well. Customers are onboarding successfully, relationships are strong, and retention is solid. But we are entering the next phase of growth where we need:
• Onboarding is measurable, scalable, and efficient
• Product readiness and activation are clearly defined
• Customer health is predictive, not reactive
• CSM time is spent where it creates the most value
• Customers are segmented intentionally, not accidentally
• Success is measured by Net Revenue Retention (NRR) across software and payments
• This role exists to institutionalize excellence, bring structure without slowing momentum, and build a Customer Success organization that scales with the company for the next decade
• You will define and operationalize what great looks like at every stage of the customer lifecycle
• Establishing clear definitions of product readiness, activation, and ongoing adoption
• Designing onboarding with measurable outcomes and clear exit criteria
• Ensuring onboarding outcomes set the foundation for long-term success
• Aligning Customer Success, Product, Sales, and Support around shared definitions of customer progress
• Clarifying ownership across teams—what CS handles, what Support handles, and where Product must improve
• Today, customer attention is not always aligned with customer impact. You will change that
• You will design and implement a segmentation model that defines:
• Customer tiers based on revenue, complexity, payment volume, and strategic value
• Engagement models for each tier (high-touch, tech-touch, pooled, automated)
• Which customers receive a named CSM
• Onboarding experience by tier (self-serve, guided, white-glove)
• You will build a customer health model that is:
• Objective, not intuition-based
• Predictive, not reactive
• Actionable for CSMs
• Identifying leading indicators of churn and expansion
• Integrating both software usage and payments data
• Translating health signals into clear operational actions
• Partnering with Product, Engineering, and Data to surface these insights directly in the tools CSMs use every day
• Customer health should guide behavior—not just sit in a dashboard
• Retention is table stakes. The next phase of CS is driving Net Revenue Retention
• Align CS metrics and incentives around NRR
• Integrate adoption, expansion, and payments growth into CS workflows
• Ensure CSMs are rewarded for long-term customer value, not short-term saves
• Encourage transparent conversations around downgrades and churn so the organization can learn and improve
• You are inheriting strong teams with strong leaders. Your job is to elevate the organization, not micromanage it
• Coach and develop the Customer Success Director
• Create clear career paths, expectations, and performance frameworks
• Introduce scalable processes and operating rhythms
• Build reliable reporting, forecasting, and executive visibility into the health of the customer base
• What Success Looks Like:
• Clear definitions of product readiness, activation, and success
• Onboarding that is measurable and scalable
• A trusted customer health model used daily by CSMs
• Account tiering that aligns effort with customer value
• Data-driven digital CS programs that enable scalable one-to-many customer engagement
• AI embedded in CS workflows to surface insights and automate routine actions
• Systems that support account planning, activity tracking, whitespace analysis, and expansion forecasting
• Improved Net Revenue Retention across software and payments
• CSM time focused on the right customers at the right moments
• A Customer Success organization built to scale with the company