Establish and manage toward the long-term vision for the Customer Success organization in alignment with TbT’s growth strategy and mission
Lead and scale a high-performing Engagement Management team, building the structure, systems, and culture needed to deliver exceptional experiences and outcomes at scale
Own team capacity planning and headcount strategy to ensure resources align with customer segmentation and business priorities
Champion a culture of accountability, learning, and service excellence across the post-sale organization
Own retention and expansion targets across our portfolio of accounts
Equip the team with playbooks, tools, and customer insights to enable strategic renewals and growth
Establish and maintain a real-time view of customer health across the portfolio—defining signals and leading indicators that require intervention or may foreshadow churn
Partner closely with Sales and Account Executives to grow accounts from multiple angles and foster a culture of collaboration
Be data informed and work the BizOps team to forecast renewals and track growth
Design and operationalize customer journeys that meet the needs of diverse customers while remaining scalable
Be a strategic thought partner and occasional executive sponsor on high-stakes accounts
Champion the voice of the customer internally - working across teams to improve our offering, delivery, and service models
Maintain an evolving perspective on the role of AI and automation in service delivery, identifying opportunities to improve efficiency without sacrificing quality and trust
Lead cross-functional initiatives to improve our overall customer experience and internal systems
Track success metrics and share insights regularly with senior leadership
Requirements
10+ years of experience in customer success, account management, operations, or a related field, ideally in a service-based or tech-enabled services organization
A track record of managing and scaling teams, including coaching managers and building strong team culture
Strong enterprise relationship management experience—especially with complex, multi-stakeholder clients (education, healthcare, public sector, or similar)
Experience designing and implementing customer success strategies, including segmentation, playbooks, and account planning
Excellent communication and influencing skills, with the ability to inspire a team and build trust with executive-level partners
An operator’s mindset: strong process builder, project manager, and strategic thinker who can also roll up their sleeves
Comfort working in a fast-paced, evolving environment—TbT is a startup, and that means adaptability is key
A passion for education equity and a belief in the power of high-dosage tutoring to change student outcomes