Sales Development Representative

Summary

Join Cartwheel, a company tackling the student mental health crisis, as a Sales Development Representative (SDR). This full-time, remote W2 position involves prospecting for new school district partners, building relationships, and understanding their needs. You will be the first point of contact for many districts, identifying alignment between Cartwheel and district priorities. The role requires exceeding sales goals in a metrics-driven environment, strong communication skills, and the ability to travel up to 25%. Cartwheel offers competitive compensation, excellent benefits, and a team-based culture. This is an opportunity to make a real difference in the lives of students while working for a well-funded startup.

Requirements

• Prior experience prospecting in sales development or similar role
• Track record of exceeding goals in a metrics-driven sales environment
• Ability to persevere through multiple rejections
• Excellent verbal and written communication skills along with skilled active listening
• Experience translating account-level research into personalized messaging
• Demonstrated ability leading a sales conversation and overcoming objections
• Demonstrated responsiveness to feedback
• 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
• Comfort with operating in a startup environment and helping to build the playbook as we go
• Ability to travel up to 25% for conferences and in-person team retreats

Responsibilities

• Complete 40 - 70 prospecting activities daily, including calls and emails
• Collaborate closely with an Account Executive(s) to create and execute on a territory plan to hit sales goals
• Source new leads for Cartwheel to engage, as well as follow-up with inbound leads sourced via marketing activity
• Engage district leaders via phone and email to schedule initial meetings
• Attend conferences and trade shows to represent Cartwheel and network with district leaders
• Collaborate with a growing Sales Development team to identify and scale best practices

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 (like Salesforce or Hubspot) and a pipeline management platform (like Outreach.io)
• Experience working in K-12 education technology

Benefits

• Competitive cash compensation including a base salary + performance bonus (on target earnings of $75-90k/year)
• Excellent health insurance
• Meaningful equity ownership stake
• 3 weeks of Paid Time Off
• Remote work environment with in-person team retreats
• 401K with employer match
• Annual education stipiend
• Macbook