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 students life

Kids shouldnt 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 theyre excited to live. If you join Cartwheel youll help make this vision a reality for millions of students across the country. Were backed by top investors including A Street Ventures Menlo Ventures Reach Capital General Catalyst BoxGroup and Able Partners and were looking for mission-driven teammates to join our team.

ABOUT THE ROLE

The School Sales team is on the front line sharing Cartwheels mission with school districts deeply understanding their needs and offering Cartwheels 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

Role type: W2 Full-Time Salaried position
Location: Remote
Start Date: March 2026

WHAT YOULL DO

• Complete 30 - 60 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

• 2 years of outbound sales or sales development experience with direct ownership of cold calling and email outreach tied to meeting or pipeline targets
• Experience selling into education and/or healthcare environments where credibility trust and longer buying cycles matter
• Strong written communication skills with the ability to translate account-level research into thoughtful personalized outreach
• Comfortable with cold calling and leading early sales conversations with district stakeholders
• Coachability you actively seek feedback and apply it quickly to improve performance
• Process-oriented and detail-driven with strong follow-up habits and CRM discipline
• Collaborative mindset able to partner closely with AEs and Sales Development leadership
• Comfortable operating in a growth-stage (Series B) environment where priorities evolve and quality matters more than pure volume

Extra Credit

• Direct experience selling EdTech solutions to K12 school districts
• Background in education or mental health (e.g. former teacher counselor social worker or school administrator)
• Experience working with Salesforce and sales engagement tools (e.g. Outreach Salesloft Apollo)
• Exposure to seasonal or extended sales cycles particularly in public-sector or district purchasing environments

Please apply even if you dont meet all of the criteria. If your past experience doesnt perfectly match the job description but you bring other relevant experience or skills wed still love to hear from you. You may be a great fit!

WHY YOULL 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 youll have:

• Mission-oriented and inclusive colleagues who will go to bat for you
• Competitive cash compensation including a base salary performance bonus (on target earnings of $90k-100k/year)
• Generous PPO medical vision and dental/ortho coverage
• Life Insurance
• Generous paid time off including company closure from Christmas-New Years (12/25-1/1)
• Paid holidays and sick leave
• Paid parental leave
• 401K with employer match
• Meaningful equity ownership stake in Cartwheel
• Flexible and remote role with regular in-person retreats
• Annual learning stipend
• Laptop

Cartwheel is proud to be an equal opportunity employer. We embrace diverse backgrounds and perspectives and an inclusive work environment. Were committed to equal employment opportunity regardless of race color religion ancestry national origin gender sexual orientation disability status or veteran status.

We participate in E-Verify. Please be prepared to provide acceptable documentation to verify your identity and work authorization

Note: Please do not contact our Care Provider or Patient Services lines regarding job postings or application status. These teams support our patients and families and are not involved in the hiring process. For all recruitment-related questions please email