Account Executive

Summary

Join Cartwheel, a company tackling the student mental health crisis, as an Account Executive on the School Sales team. You will help expand our partnerships by guiding interested districts through the sales process. This role involves presenting Cartwheel's services, building relationships with school districts, and collaborating with internal teams. The position is remote with some travel, primarily focused on the Northeast. We offer competitive compensation, excellent benefits, and a mission-driven team environment. This is a full-time, salaried W2 position starting in March/April 2025. We are looking for a top performer with experience selling to K-12 school districts.

Requirements

• At least 3 years of experience selling to K-12 school districts with experience selling to districts in the Northeast and/or Great Lakes states
• Located in New England, New York or another Northeast state
• 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!

Responsibilities

• 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

Preferred Qualifications

• 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)

Benefits

• Team-based culture with mission-driven colleagues who will go to bat for you
• Flexible and up to 100% remote role
• Competitive cash compensation of $140,000 - $160,000 + commission and will be determined based on experience and qualifications
• 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