Enterprise Customer Success Manager – Public Sector

CartwheelCambridge, MA
$143,000 - $187,000Remote

About The Position

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.

Requirements

  • 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

Nice To Haves

  • 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

Responsibilities

  • 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.
  • 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

Benefits

  • 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
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