Vice President of Customer Success

Summary

Join Tutored by Teachers (TbT) as the Vice President of Customer Success and lead a team of Engagement Managers, ensuring school and district partners maximize the value of high-dosage tutoring programs. Build lasting relationships with partners, scale customer success experiences nationwide, and manage retention and growth targets. Develop and implement customer success strategies, including segmentation and playbooks. Champion a culture of accountability, learning, and service excellence. Collaborate with Sales and Account Executives to foster growth and act as a strategic thought partner on high-stakes accounts. Maintain an evolving perspective on AI and automation in service delivery and lead cross-functional initiatives to improve customer experience.

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

Responsibilities

• 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

Preferred Qualifications

• Low ego, low drama, servant leader. You share credit, take blame. You like being wrong because it means someone else had an even better idea
• One team mentality. You break silos across teams. You put the company and mission first above your team alone
• Great listener, hungry for feedback. You’re always seeking to improve – our product, our business, yourself. You solicit diverse opinions and deeply listen
• Owner, not renter. You see a problem, you fix it or find someone who will. The buck stops with you
• Player-coach. You fly high (create strategy) AND low (know the details that matter). You roll up your sleeves and get scrappy. You do this without micromanaging, empowering your team while actively engaging in important details
• Business problem solver. You’re not just a functional expert; you consistently get praise for approaching your function through the lens of solving business problems
• Information worker. You aggressively, directly, and succinctly communicate up, down, left, and right using the right channels

Benefits

• 100% healthcare coverage for you and your family
• Access to 401k to help save for the future
• Well-rounded wellness benefits, including access to free and low cost mental health resources and support services
• Fully remote work environment and a flexible schedule
• Annual in-person team retreats
• 3 weeks of vacation in the first year and an unlimited vacation policy after year 1 to help recharge
• The chance to make a meaningful impact on students' lives and contribute to the advancement of educational equity