Great mission and pay, but management needs improvement - Customer Success Manager Cartwheel (MA) Employee Review

Cartwheel has a culture that genuinely stands out. Leaders model vulnerability and transparency in a way that’s rare — they openly share context, mistakes, lessons, and decisions, which creates real psychological safety across the team. You’re encouraged to speak up, ask questions, challenge assumptions, and bring ideas forward without fear of backlash. The environment is fast-paced and evolving, but it’s grounded in kindness, trust, and a shared commitment to doing the right thing for students, families, and schools. It’s the kind of place where you feel valued as a human, not just an employee. Pros: Transparent and vulnerable leadership, high psychological safety, collaborative team, mission-driven work, real opportunities to build.

Cons: Fast pace and shifting priorities may be challenging for those who prefer structure.

Good electronic health record, good internal communication via Slack, ability to work as much or as little as you like, consistent flow of clients, ability to work with children who would otherwise not get Mental Health services

It appears that the primary client is school districts which potentially puts the therapist in a conflict of interest situation. We consider the client or the child as primary whereas the therapist is part of a bigger system. making it’s difficult to advocate, for the child if necessary. Limited understanding of complexities of providing true Mental Health services to children in the face of difficult family dynamics. Willingness to throw the Therapist under the bus when these challenges manifest