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.
With large increases in federal funding for schools and the rise of telehealth, schools are reimagining what mental health support can look like.
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.
ABOUT THE ROLEYou’ll help Cartwheel deepen our partnerships with existing district partners and develop Cartwheel’s playbook for winning renewals and expansions year on year. In doing so, you’ll expand our impact within each district, grow our revenue base, and reinforce Cartwheel’s role as the trusted mental health partner in the communities we serve.
Role type: Full-Time
Location: Fully remote with regional travel 1-3x a quarter; preference for location in the Southern US and ability to work EST or CST hours
Start: July 2026
Compensation: $115,000 - $135,00 a year plus 20% base incentive plan and competitive equity options
- Develop and own Cartwheel’s “best practice” approach for securing renewals and expansions on our existing contracts
- Forecast and manage our renewal and expansion pipeline
- Develop growth strategies for individual accounts, identifying opportunities to expand services through cross-sell, upsell, and expansion opportunities. Build a thesis for each account on what it will take to win.
- Capitalize on expansion opportunities to position and secure renewal
- During implementation, collaborate with the Sales and Success teams to ensure a smooth handoff and implementation after the initial sale closes
- Throughout the partnership
- Nurture relationships across the district to ensure broad sponsorship for Cartwheel (e.g., Superintendents, Student Services, Counseling)
- Work with School Success to share impact stories, prove Cartwheel’s ROI, and collect feedback on our product and show how we’re responding to it
- Explore opportunities to expand, upsell, or cross-sell
- During the annual renewal process, lead contract negotiations with district leadership, procurement teams, and key stakeholders, including counseling them on how to creatively leverage funding sources and adhere to our timeline
- 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 team performance
- Embodies our values: Human, Humble, Accountable, Innovative, Resilient
- Has 6-10 years of sales and/or account management experience within K-12 education
- Fluent in the "full stack" sales and renewal motion, with a keen understanding of:
- Rapidly building a broad base of authentic, trusting relationships
- Discovering the needs, preferences, and obstacles in each district
- Efficiently managing your pipeline and forecasts
- Handling objections and creatively finding solutions
- Counseling districts on the nuances of a complex market and product
- Closing deals and building sponsorship across the district along the way
- Negotiating on pricing, deal construct, timelines, and incentives
- Corralling diverse stakeholders to adhere to a concrete timeline
- 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:
- Competitive compensation between $145,000 - $168,000 (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 up to 2% employer match
- $500 annual educational stipend
- 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.
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. This may include tools that help organize and surface applications for recruiter review, AI-powered candidate communications and scheduling, interview recording and documentation, and an AI chat tool available to candidates during the process. All hiring decisions are made by Cartwheel recruiters and hiring managers. No candidate is selected or eliminated from consideration solely by an automated system. All hiring decisions are made by humans. If you have questions about how AI is used in our process or would like to request an alternative review method, please contact [email protected]
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 [email protected].
Skills Required
- 6-10 years of sales and/or account management experience within K-12 education
- Proven experience securing renewals and expansions on existing contracts
- Forecasting and managing renewal and expansion pipelines
- Experience developing growth strategies, identifying cross-sell/upsell/expansion opportunities
- Contract negotiation experience with district leadership and procurement teams
- Ability to build and nurture relationships with district stakeholders (Superintendents, Student Services, Counseling)
- Experience counseling districts on funding sources, timelines, and complex market/product nuances
- Ability to work EST or CST hours (preference for Southern US location)
- Excellent communication skills and ability to prioritize and execute in a fast-growing startup environment
What We Do
We believe that 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. Cartwheel is the trusted mental health partner to schools. We deliver rapid access to care for students and help schools build stronger mental health programs that catch kids before they fall.
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