Enterprise Account Executive

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 Menlo Ventures, Reach Capital, General Catalyst, BoxGroup, and Able Partners, and we're looking for mission-driven teammates to join our team.

As an Enterprise Account Executive on the School Sales team, you will help us build on our early success – 200+ district partnerships across 13 states – by taking interested districts through the sales process from initial presentation to close. As we continue to expand, you’ll be part of the team that makes Cartwheel a household name for supporting school district mental health programs! 

Cartwheel’s School 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 school district partners and go above and beyond in supporting them throughout the sales process. 

This role is primarily focused on districts of enrollment 20,000+ and candidates must have ample experience selling into this customer profile. Candidates must demonstrate a keen understanding of enterprise sales motions and speak clearly to their ability to strategize and execute against a well constructed plan. 

Role type: This is a W2, Full-Time, Salaried position

Location: US Remote with some travel. Preference for candidates based in the Northeast (New England, NY, etc.)

Start date: Summer 2025

• Be the face of Cartwheel in a set of states. You’ll introduce Cartwheel to interested districts virtually and in-person (for significant meetings and at conferences) 
• Collaborate with Sales Development Representatives on outbound prospecting strategy in your sales territory to start conversations with school districts that may be a good match for Cartwheel’s services
• Collaborate with members of the marketing team on initiatives for generating inbound interest in your sales territory 
• Deeply understand the current state of mental health support in school districts, ask questions to uncover existing needs and priorities in districts, and position Cartwheel as a solution to those needs and priorities
• Build strong and trusting relationships with school district main points of contact to help them navigate the buying process in their district
• Lead tailored presentations on Cartwheel to school district decision-makers (Superintendents, Assistant Superintendents and Directors) virtually and, on occasion, in-person
• Share pricing and project scopes with district buying committees and help them find creative ways to fund Cartwheel’s work 
• 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 

Must have…

• At least 6+ years of experience selling to enterprise K-12 school districts with experience selling to districts in the Northeast and/or Great Lakes states
• Ability to travel up to 40% to meet with prospective clients and attend conferences (busy travel season of January-June)
• Demonstrated success as a top performer (exceeding goals and quota) with a consultative sales mindset
• Experience presenting virtually and in-person across a variety of stakeholders 
• Experience preparing error-free client-facing materials (proposals, email communication, etc.)
• A demonstrated ability to steer a conversation by pivoting quickly, overcoming objections, and solving problems in the moment 
• Experience synthesizing information gathered through research and conversation, and connecting that information to Cartwheel’s solution 
• Strong organizational and time-management skills, with the ability to juggle multiple sales opportunities with competing timelines at once
• An openness to collaborate frequently and productively with sales development and marketing team members 
• Passion working with schools on mental health issues 
• A competitive spirit – we love to win on the school sales team and will celebrate our wins together and learn and improve from our losses!

Extra credit…

• Located in New England, New York or within territory
• Experience working in schools (as a teacher, administrator, counselor, social worker or other support staff member)
• Proficiency or expertise in using a CRM and a pipeline management platform (like Outreach.io)

The above is a summary of the role, not an exhaustive list. If you think that you have most of the above but not everything, please apply. We'd love to hear from you.

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
• Flexible and up to 100% remote role 
• Competitive cash compensation OTE starting at $200,000 on a 60/40 split and base salary depending on experince.
• Excellent health insurance 
• Flexible paid time off
• Equity ownership stake in the company
• Administrative support from our experienced, full-time Care Coordinators
• Leadership role in fast-growing company

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.