Director of Customer Success

Apply Job Type Full-time Description The Director of Customer Success owns the architecture and execution of the customer success function at Books Are Fun. This is a builder role at a senior level. The CS organization is growing, the program is proven, and the retention opportunity is significant. What it needs now is a leader who can design the methodology, build the structure, and develop the team that turns a strong program into a predictable retention engine. This role is responsible for designing and installing a split CS model that separates new business execution from renewal management, building the account segmentation framework, establishing the handoff process between tracks, and developing the leadership team that runs both. The Director of Customer Success is not inheriting a finished system. They are building one. This role reports to the CRO and is expected to operate with strategic authority, clear ownership, and a bias toward execution. The right person has done this before and can prove it. Key Responsibilities: Design and install a split Customer Success model separating new business execution (Track 1) and renewal management (Track 2) with defined ownership, handoff criteria, and performance standards for each. Build the account segmentation framework that assigns schools to Large, Medium, and Small renewal tiers based on revenue concentration, complexity, and renewal risk. Establish the handoff process between the New Business CSM track and the Renewal CSM track, ensuring continuity of relationship and no loss of context at transition. Own retention performance across the full CS organization, with targets of 65% in 2026, 75% in 2027, and 85% in 2028. Lead, develop, and hold accountable a team that includes the New Business CSM Director, CSM Trainer, Renewal CSMs, and CSM Leads. Build the renewal cadence, risk detection framework, and save process that drives forecast reliability and reduces attrition blast radius. Partner with the CRO, RVP team, and BBOS to ensure clean handoffs from sales to CS and aligned expectations at the point of sale. Develop career paths, performance standards, and coaching frameworks that make the CS team a place people grow. Own CS forecasting and provide the leadership team with accurate, timely visibility into renewal pipeline and retention risk. Partner with Marketing, Operations, and Product to surface customer insights and translate them into program improvements. Duties: Establish and run weekly CS leadership rhythms including pipeline reviews, renewal risk assessments, and team performance conversations. Design and document the split model methodology including playbooks, segmentation criteria, handoff protocols, and escalation paths. Own the CS technology stack in partnership with Rev Ops and IT, ensuring HubSpot and supporting tools reflect and support the CS workflow. Build and maintain CS performance dashboards that make retention metrics visible and actionable for the leadership team. Conduct regular account reviews on high-risk and large-tier renewals, involving RVPs strategically when warranted. Hire, onboard, and develop CS talent as the organization scales toward 2027 and 2028 targets. Participate in cross-functional leadership meetings as a senior voice on customer health, retention risk, and program quality. Perform other related duties as required to build and sustain a world-class CS organization. Requirements Key Requirements: Proven experience building a Customer Success methodology from scratch in a recurring revenue business. Approaches AI as infrastructure, not a feature. The CS function here will be built to capture and act on signal across every customer touchpoint. The right candidate is already thinking about how meeting intelligence, risk scoring, and automated nurture fit into a modern CS organization. Direct experience designing or operating a split CS model separating execution and renewal tracks. Track record of owning and improving retention metrics in a high-volume, program-based, or subscription environment. Strong people leader with experience developing CS managers and building career paths that reduce attrition and increase depth. Exceptional process and systems thinker with the ability to design frameworks that scale without breaking. Proficiency with HubSpot or comparable CRM, with a hands-on approach to data, forecasting, and pipeline visibility. Clear, direct communicator who earns trust with frontline teams and credibility with executive leadership. Experience in education, childcare, or mission-driven environments a plus. Genuine passion for literacy and the mission of Books Are Fun. Approaches AI as infrastructure, not a feature. The CS function here will be built to capture and act on signal across every customer touchpoint. The right candidate is already thinking about how meeting intelligence, risk scoring, and automatednurture fit into a modern CS organization. Working Conditions: Remote position with periodic travel to the home office and key team or customer events. Physical Requirements: Prolonged periods of sitting at a desk and working on a computer. Must be able to lift up to 10 pounds at times.