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Enterprise Customer Success Manager – Public Sector

Cambridge, MA

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 A Street Ventures, 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

In 3 years, Cartwheel has grown to serve more than 325 school districts in 16 states, making us the nation’s largest mental health provider that collaborates with K-12 schools. With billions of dollars in new state and federal investments in youth mental health coming in 2026, we are supplementing our district-level sales motion with statewide partnerships with Governor’s offices, education departments, and health agencies.

As the Enterprise Customer Success Manager, you will be Cartwheel's primary point of contact with the state agency, responsible for turning a signed contract into a high-impact, expanding program. That means building the implementation plan, coordinating execution across Cartwheel's internal teams, keeping agency staff informed and confident, and clearing whatever is in the way of delivering exceptional impact. Throughout the contract period, you’ll partner closely with our Government Relations teams, which will own executive and legislative relationships and the contract renewal process.

Role type: W2, Full-Time, Salaried position
Salary range: $143,000 – $187,000 OTE (10% variable pay included) plus competitive equity package
Location: Remote
Target Start: June 2026

WHAT YOU'LL DO

Own the state agency relationship

  • Be the primary Cartwheel contact for agency program directors, behavioral health leads, and operational staff — the people responsible for implementing the partnership. 
  • Build a deep understanding of agency priorities, constraints, and decision-making so you can navigate complexity and keep things moving
  • Develop and maintain a comprehensive contact map across agency implementers, influencers, and financial buyers — and build productive relationships across each layer
  • Lead regular agency check-ins covering progress, milestone tracking, and issue resolution
  • Navigate agency political dynamics, policy constraints, and interagency complexity
  • Develop success stories as implementation matures to support renewal and expansion

Drive implementation

  • Build and own the implementation plan for your state(s): What needs to happen, in what order, by when, and who is responsible
  • Develop a district prioritization framework: Where to start, how to sequence expansion, how to pace growth against contract timelines
  • Own and track the metrics that matter — utilization, district activation, contract milestone attainment — and surface risks early before they become problems
  • Coordinate across internal Cartwheel teams to ensure we meet all of our impact goals and milestones. For example:
    • Partner with the Government Relations team on renewal readiness and ensure they have an excellent value story to share with executive and legislative buyers
    • Ensure district-level sellers and CSMs are effectively onboarding districts
    • Coordinate with Operations to clear compliance, credentialing, and regulatory hurdles that slow implementation down
  • Engage state-level professional associations (superintendent associations, state education agencies) to support district activation and strengthen Cartwheel's presence

Keep leadership and the team aligned

  • Maintain clear, multi-quarter visibility into contract health and district-level risk
  • Report out on contract health to Senior Leadership and share insights on how to improve our approach to state implementations, product innovation, or other key insights
  • Identify expansion opportunities (new districts, expanded services, adjacent agency relationships) and surface them to Government Relations and internal teams to pursue

WHAT WE’RE LOOKING FOR

Required

  • 7–10+ years in customer success, strategic account management, or a closely related post-sale role, with meaningful experience in government or public sector
  • You're an exceptional communicator — able to translate operational complexity into clear reporting for agency partners and internal leadership
  • You've built trusted relationships with state or government agency staff. Not just executives, but program officers and operational leads
  • You've managed complex, multi-stakeholder account plans and can connect the dots between day-to-day execution and long-term contract health
  • You understand the revenue implications of implementation decisions and take ownership of retention outcomes
  • You can navigate political and bureaucratic dynamics without losing momentum
  • You are comfortable interpreting data on your own and communicating insights
  • You're highly organized and comfortable building structure in an environment that doesn't have all the answers yet

Preferred

  • Experience in K–12 education, healthcare, or direct service businesses
  • Familiarity with braided funding models (state contracts, Medicaid, grants, district fees)
  • Background working alongside or within Government Relations or public affairs functions
  • Experience with state procurement processes and compliance relevant to public sector
  • Familiarity with ChurnZero, Gainsight, Salesforce, or HubSpot

Travel

This role requires regular travel — approximately 40% — to support state agency relationships, district engagement, and key implementation milestones, concentrated in your assigned state(s).

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:

  • Mission-oriented and inclusive colleagues who will go to bat for you
  • Competitive compensation
  • Generous PPO medical, vision, and dental/ortho coverage
  • Life Insurance
  • Generous paid time off, including company closure from Christmas-New Years (12/25-1/1)
  • Paid holidays and sick leave
  • Paid parental leave
  • 401K with employer match
  • Meaningful equity ownership stake in Cartwheel
  • Flexible and remote role with regular in-person retreats
  • Annual learning stipend
  • Laptop 

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.

We participate in E-Verify. Please be prepared to provide acceptable documentation to verify your identity and work authorization

Cartwheel uses AI-assisted tools to support our hiring process, including scheduling, communications, and workflow management. All hiring decisions are made by humans. We are committed to fair, equitable hiring practices

Note: Please do not contact our Care, Provider, or Patient Services lines regarding job postings or application status. These teams support our patients and families and are not involved in the hiring process. For all recruitment-related questions, please email talent@cartwheelcare.org.

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