Manager of Customer Success

Summary

Join Cartwheel, a company tackling the student mental health crisis, as a Manager of Customer Success. Lead and develop a team of Customer Success Managers, driving contract implementation, customer retention, and renewals across the US. As a strategic leader, ensure school district partners achieve positive outcomes while fostering a high-performing team culture. This role blends people leadership, revenue ownership, and K-12 systems understanding. Partner with cross-functional teams to shape customer success strategy and serve as an escalation point for critical customer needs. The position is remote in the US with regular in-person team retreats. Cartwheel is backed by top investors and seeks mission-driven individuals.

Requirements

• 2+ years of people management experience (Customer Success management strongly preferred, but will consider management experience in adjacent functions)
• 5+ years of experience in a Customer Success role with responsibility for both implementation and renewals, and ARR of at least $3M with a proven, consistent track record of exceeding goals
• Direct experience working in or with K-12 school systems as an individual contributor or manager
• Experience with data-driven customer health scoring and risk mitigation strategies
• Demonstrated ability to build trust and influence across diverse stakeholders including school administrators, teachers, and clinical staff
• Commitment to serving communities traditionally overlooked in healthcare – uninsured and underserved families, youth in foster care, English learners, etc
• Passion for tackling the youth mental health crisis through systemic change

Responsibilities

• Hire, retain, and develop a team of Customer Success Managers with shared responsibility for customer impact, adoption, and renewals
• Foster a culture of teamwork, collaboration, and continuous learning while maintaining high expectations in a rapidly evolving startup environment
• Coach CSMs on navigating complex customer challenges including stakeholder engagement, driving adoption and renewals, risk mitigation, and retention strategies
• Conduct regular 1:1s, biannual performance reviews, and career development conversations to grow your team's capabilities
• Build strong executive relationships with district decision makers, champions, and project leaders across your team's portfolio
• Act as a strategic thought partner and point of escalation for high-stakes customer situations
• Develop and implement strategies to proactively identify and manage risks and opportunities across all school district contracts
• Ensure consistent delivery of exceptional customer experiences that drive renewal and expansion
• Own revenue retention targets and guide your team to achieve renewal goals
• Create and refine scalable processes that enable the team to effectively manage a growing portfolio of districts
• Partner with Sales, Clinical, and Product teams to ensure seamless customer journeys
• Analyze customer health metrics and provide strategic recommendations to leadership
• Build proactive, collaborative relationships with internal crossfunctional partners across Cartwheel
• Represent the voice of the customer to inform product development and operational improvements
• Work closely with Sales to ensure smooth handoffs and alignment on customer success strategies

Preferred Qualifications

• Experience scaling Customer Success teams in early-stage startups
• Background in educational technology or school-based mental health programs
• Experience working with clinical care teams in mental health or healthcare contexts
• Leadership Excellence: Proven ability to lead with a direct, kind, and human-first approach, and a willingness to have hard conversations early and often
• Strategic Communication: Exceptional written and verbal communication skills with ability to influence executive stakeholders and navigate complex, sensitive situations diplomatically
• Operational Excellence: Strong project management and organizational skills to coordinate across multiple priorities and drive consistent execution
• Systems Thinking: Deep understanding of educational systems and ability to navigate school district dynamics effectively
• Entrepreneurial Mindset: Thrives in ambiguous, fast-paced startup environments with resilience to handle high-pressure situations
• Technical Proficiency: Fluency in CRM systems (e.g. Salesforce, Gainsight), Google Suite, and ability to quickly adopt new tools and technologies

Benefits

• Competitive cash compensation between $160,000-180,000 OTE
• Equity ownership stake in the company
• High-quality health insurance with a $0 monthly premium option for employees
• Dental, Vision, and Employer-Sponsored Life Insurance
• 4 weeks of paid PTO (3 weeks any time + 1 week office closure in December)
• Sick Leave + Holidays
• 401K with 2% employer match