Sales Development Representative Cambridge, MA

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:

• 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 A Street Ventures, Menlo Ventures, Reach Capital, General Catalyst, Box Group, and Able Partners, and we're looking for mission-driven teammates to join our team.

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.

Role type: W2, Full-Time, Salaried position

Location: Remote

Start Date: March 2026

• 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

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
• Direct experience selling EdTech solutions to K–12 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 don't meet all of the criteria. If your past experience doesn't perfectly match the job description, but you bring other relevant experience or skills, we'd still love to hear from you. You may be a great fit!

• 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…