| Director of Customer Success Location: Remote (U.S.) Reports to: VP of Customer Success About CINC Systems CINC Systems is the leading provider of accounting and management software for the community association management industry. Our platform supports tens of thousands of associations and millions of homes, providing critical financial and operational capabilities in a highly reliable, multi-tenant SaaS environment. Position Overview We are seeking a highly operational and execution-focused Director of Customer Success to lead a team of Customer Success Managers (CSMs) responsible for driving customer adoption, value realization, and renewals across our SaaS customer base. This role is a critical leader within the Customer Success organization, responsible for executing against and playing an integral part in the evolution of our strategy. The Director will translate strategic priorities into scalable processes, team execution, and measurable customer outcomes. The ideal candidate excels at operationalizing strategy, managing escalations, and driving consistency at scale and combines strong operational rigor with hands-on experience leveraging AI, automation, and data analytics to scale customer engagement, improve health visibility, and optimize renewal and expansion outcomes. Key Responsibilities Strategy Execution & Operational Leadership - Execute and evolve against the customer success strategy and segmentation model
- Translate strategic priorities into clear workflows, playbooks, and team-level execution plans
- Ensure consistent adoption of processes across the CSM team to drive scalable and repeatable outcomes
- Identify gaps in execution and provide recommendations to leadership for continuous improvement
Team Leadership & Performance Management - Lead, coach, and develop a team of Customer Success Managers responsible for adoption, CSQLs, and renewals
- Drive accountability to core KPIs including adoption, engagement, expansion & renewal readiness, and customer health
- Establish a strong operating cadence including 1:1s, pipeline reviews, and performance management
- Foster a culture of proactive customer engagement and operational excellence
Renewal Readiness & Customer Lifecycle Execution - Ensure customers are effectively guided through onboarding, adoption, and value realization milestones
- Drive renewal readiness activities, including risk identification, mitigation planning, and executive alignment
- Partner with leadership and account teams to support renewal outcomes through strong execution and visibility
- Standardize lifecycle playbooks to ensure consistency across customer segments
Digital Segmentation & Scaled Engagement - Build and operationalize a digital segmentation approach to support scaled customer engagement across lower-touch segments
- Partner with leadership to align digital coverage to overall segmentation strategy, ensuring consistency with broader CS priorities Develop automated, tech-touch engagement models (ex: lifecycle campaigns, adoption focused campaigns)
- Leverage CS platform and AI-driven tools to deliver personalized, scalable customer interactions
- Continuously optimize digital programs based on engagement data, adoption trends, and customer feedback
Escalation Management & Risk Mitigation - Own and manage customer escalations, ensuring timely resolution and clear communication
- Act as a senior point of contact for at-risk customers, coordinating cross-functional resources as needed
- Implement structured escalation management processes and root cause analysis
- Drive proactive risk identification through customer health signals and team insights
Cross-Functional & Enterprise Partnership - Partner closely with the Strategic Account teams to align on account strategy, risks, and opportunities
- Support complex and high-value accounts by ensuring coordinated execution across Customer Success
- Collaborate with Support, Product, Implementation and Sales to resolve customer issues and improve overall experience
- Provide structured feedback to Product and leadership based on customer insights and trends
Process, Systems & Automation - Execute and optimize workflows within CS platforms (ex: Salesforce, ChurnZero, Intercom)
- Support the implementation of automation and AI-driven tools to improve efficiency and customer visibility
- Ensure data integrity and consistent usage of systems across the team
- Identify opportunities to streamline processes and reduce manual effort
Customer Health & Data-Driven Execution - Operationalize customer health scoring frameworks defined by leadership
- Monitor customer health trends and ensure timely action on risk signals
- Leverage data and reporting to guide team activity and prioritize customer engagement
- Provide insights and feedback to leadership on trends impacting retention and adoption
Qualifications - 7–10+ years of experience in Customer Success or Account Management
- 3–5+ years of experience leading Customer Success or account management teams
- Proven ability to execute within a defined strategy and drive consistent team performance
- Experience managing escalations and working with complex or high-value customer accounts
- Hands-on experience with CS platforms (ex: Salesforce, ChurnZero, Intercom)
- Strong operational mindset with experience building and improving processes and workflows
- Data-driven approach with the ability to translate insights into action
- Excellent communication and cross-functional collaboration skills
Key Metrics for Success - Gross Revenue Retention (GRR)
- Net Revenue Retention (NRR)
- Customer Adoption & Engagement Levels
- Renewal Readiness & Risk Mitigation Effectiveness
- Customer Health Score Trends
- Escalation Resolution Time & Outcomes
- Team Productivity & Process Adherence
- Forecast Input Accuracy (supporting leadership-level forecasts)
What Success Looks Like in This Role - Gross Revenue Retention (GRR) targets are consistently achieved through proactive risk mitigation and disciplined execution
- A highly consistent and scalable CSM organization executing effectively against defined strategy
- Strong visibility into customer health, risks, and renewal readiness
- Escalations are proactively managed with minimal customer disruption
- Tight alignment with Enterprise teams on high-value accounts
- Improved operational efficiency through process discipline and automation
Benefits: - Great working environment
- Growth opportunities
- Work/life balance
- Medical
- Dental
- Vision
- Life Insurance
- Short-term & Long-term disability insurance
- Flexible Spending Plan (childcare & healthcare)
- 401K (matching available)
- 136 hours of PTO (paid-time-off) hours per year
- 10 paid holidays per year plus bonus holiday (birthday – paid day off)
- 2 self-care/mental health days per year
- Free snacks, coffee, and Coca-Cola products (when in office)
CINC is an Equal Opportunity Employer of women, minorities, protected veterans and individuals with disabilities.
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