Manager of Customer Success

Cartwheel; Cambridge (MA); Remote; USD 160,000 - 180,000; Full time

Job summary

Cartwheel is seeking a Manager of Customer Success to lead a team focused on driving customer retention and success across K-12 partnerships. This role demands a blend of leadership, strategic communication, and an understanding of educational systems to help transform student mental health through innovative programs. Join us to make a significant impact on the lives of millions of students.

Benefits

Competitive cash compensation

Equity ownership stake

High-quality health insurance

4 weeks of paid PTO

401K with 2% employer match

Qualifications

• 2+ years of people management experience, preferably in Customer Success.
• 5+ years of experience in a Customer Success role with significant responsibility.

Responsibilities

• Lead and develop a team of Customer Success Managers.
• Build strong executive relationships with district decision-makers.
• Own revenue retention targets and guide team to achieve renewal goals.

Skills

Leadership Excellence

Strategic Communication

Operational Excellence

Systems Thinking

Entrepreneurial Mindset

Technical Proficiency

Education

Direct experience working in K-12 school systems

Tools

CRM systems (e.g., Salesforce, Gainsight)

Google Suite

Job description

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Join Cartwheel to help tackle the student mental health crisis.

Cartwheel is an early-stage company building a new kind of mental health program for kids that puts schools at the center. We see our role as supporting school staff who see kids every single day. Instead of going around them, we collaborate with them. This means:

• Earlier intervention
• Higher student and family engagement in care
• Better coordination among the trusted adults in a student's life
  
  

Kids shouldn't just aspire to get out of bed and drag themselves to class. They should be able to experience joy. They deserve to envision and build a life they're excited to live. If you join Cartwheel, you'll help make this vision a reality for millions of students across the country. We're backed by top investors including Menlo Ventures, Reach Capital, General Catalyst, BoxGroup, and Able Partners, and we're looking for mission-driven teammates to join our team.

About The Role

As a Manager of Customer Success, you will lead and develop a team of Customer Success Managers responsible for driving implementation of contracts, customer retention, and renewals across the active Cartwheel states throughout the US. You'll be the strategic leader who ensures our school district partners achieve transformative outcomes with Cartwheel while building a high-performing team culture. This role requires a unique blend of people leadership, revenue ownership, and deep understanding of K-12 systems to effectively guide your team through complex customer relationships and renewals. You'll partner closely with cross-functional teams to shape our customer success strategy and serve as an escalation point for critical customer needs.

Role type: This is a W2, Full-Time, Salaried position

Location: Remote in the US, with regular in-person team retreats

Start date: Summer 2025

What You'll Do

Team Leadership & Development

• 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
  
  

Strategic Customer Management

• 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
  
  

Revenue & Process Ownership

• 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
  
  

Crossfunctional Collaboration

• 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
  
  

Who You Are

Must have…

• 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
  
  

Extra credit…

• 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
  
  

Skills…

• 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
  
  

Please apply even if you don't meet all of the criteria. If your past experience doesn't perfectly match the job description, but you bring other relevant experience or skills, we'd still love to hear from you. You may be a great fit!

WHY YOU'LL LOVE CARTWHEEL

Our hope is that Cartwheel will be your best career decision! In addition to tackling one of the biggest challenges of our time, at a company well-positioned to do so, you'll have:

• 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
• Team-based culture with mission-driven colleagues who will go to bat for you
  
  

Cartwheel is proud to be an equal opportunity employer. We embrace diverse backgrounds and perspectives and an inclusive work environment. We're committed to equal employment opportunity regardless of race, color, religion, ancestry, national origin, gender, sexual orientation, disability status, or veteran status.

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