Enterprise Account Executive

Summary

Join Cartwheel's School Sales team as an Enterprise Account Executive and contribute to tackling the student mental health crisis. Help expand Cartwheel's reach by managing the sales process for interested school districts, from initial presentations to closing deals. Collaborate with Sales Development Representatives and the marketing team to generate leads and build relationships with prospective clients. Deeply understand the needs of school districts and position Cartwheel's services as a solution. Lead presentations to decision-makers, manage pricing and project scopes, and ensure a smooth transition to the School Success team after a sale. This role requires significant experience selling to enterprise K-12 school districts, particularly in the Northeast and Great Lakes regions, and involves up to 40% travel. The position offers a competitive compensation package, including a base salary and commission, excellent health insurance, flexible paid time off, and equity ownership.

Requirements

• 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!

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

• 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)

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 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