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Account Executive



Sales & Business Development
Cambridge, MA, USA · Remote
Posted on Tuesday, June 11, 2024

Join Cartwheel to help tackle the student mental health crisis.

Kids spend most of their days in the classroom. And teachers and staff, who play a vital role in their development, are often the first to notice when something is off. But with 1 in 5 young people struggling with mental health, schools are getting crushed by a downward spiral in student crises and staff burnout. They know it's time to reimagine what mental health support can look like for the staff, students, and families.

Cartwheel is an early-stage startup building technology-enabled mental health services that put schools at the center. We see our role as supporting on-campus counselors, psychologists, and school social workers who see kids every 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.


Cartwheel is a trusted mental health partner for schools, students, and families. Cartwheel’s Sales Team is on the front line for our company, sharing Cartwheel’s mission with school districts, deeply understanding their needs, and offering Cartwheel’s care model as a solution to those needs. As we do this, we build strong, authentic relationships with our prospective partners and go above and beyond in supporting them throughout the sales process. As an Account Executive, you’ll go deep in building Cartwheel's presence across 1-2 states, leveraging resources across the company to develop a state-level strategy, source prospective partnership, become the expert on local resources and stakeholders, and close new deals.

Location: Remote with some travel. Preference for candidates based in WI, IL, IN, OH, PA, or NY.

Start date: July 15, 2024

Reports to: Head of School Sales


  • Lead partnership development in 1-2 states.
  • Develop and own the state-level strategy (e.g., nuances of the selling motion for that particular state, must-win districts, key professional associations and conferences)
  • Prospect new potential partners with support from our core Sales Development team
  • Collaborate with members of the marketing team on initiatives for generating inbound interest in your states, leveraging your local expertise
  • Build strong and trusting relationships with school district leaders (e.g., Superintendents, Special Education, and Student Services)
  • Discover the core mental health needs within the district, possible need for Cartwheel, budget sources, and timeline to partner
  • Build a thesis for each prospective partner on what it will take to win
  • Demonstrate exceptional deal control, always maintaining a clear path to close-win, including immediate next step, possible pitfalls, and contingency plans.
  • Continually share learnings and feedback with colleagues to improve the team’s overall performance
  • Collaborate with members of Cartwheel’s School Success Team to ensure a smooth handoff between the Sales and School Success teams once a district is signed on to work with Cartwheel


  • Embodies our values: Human, Humble, Accountable, Innovative, Resilient
  • Has 3-6 years of direct sales experience within K-12 education
  • Fluent in the "full stack" sales motion, with a keen understanding of:
    • Generating leads through outbound, conferences, and networking
    • Rapidly building authentic, trusting relationships
    • Discovering the needs, preferences, and obstacles in each district
    • Efficiently managing your pipeline and forecasts
    • Counseling districts on the nuances of a complex market and product
    • Closing deals and building sponsorship across the district along the way
    • Continually improving the way you prospect, manage, and close deals
  • Thrives in a world of rapid startup growth
  • Gets stuff done and prioritizes outcomes
  • Exceptional communicator in a variety of settings and formats
  • In the face of competing priorities, prioritizes and moves forward without getting stuck


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:

  • Team-based culture with mission-driven colleagues who will go to bat for you
  • Expected cash compensation in the range of $160-190K
  • Excellent health insurance
  • Meaningful equity ownership stake
  • Flexible paid time off
  • Hybrid work environment with regular in-person team retreats
  • 401K with employer match
  • $500 annual educational stipend
  • Macbook

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.