Sales Development Representative

Join Cartwheel to help tackle the student mental health crisis. 

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.

ABOUT THE ROLE

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

Location: US Remote

Start date: July 2025

The School Sales team is on the front line 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. 

As a Sales Development Representative (SDR), you will help us find new Cartwheel partners through inbound and outbound sales efforts. As the first point of contact for many districts, the SDR role is critical to identify alignment between Cartwheel and district priorities and generate interest for further conversations.

WHAT YOU’LL DO:

• 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

WHO YOU ARE 

Must have…

• 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

Extra credit…

• 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 

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.

WHY YOU’LL LOVE CARTWHEEL

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 cash compensation including a base salary + performance bonus (on target earnings of $75-90k/year)
• 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 2% employer match
• 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.