Cartwheel · 14 hours ago
Sales Development Representative
United States
Full-time
Remote
Entry, Mid Level
$90K/yr - $100K/yr
2+ years expCartwheel is an early-stage company focused on improving student mental health through innovative programs. The Sales Development Representative will be responsible for generating leads and building relationships with school districts to promote Cartwheel's care model.
Health CareMental HealthmHealthTherapeuticsWellness
Responsibilities
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
Qualification
Required
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
Preferred
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
Benefits
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
Company
Cartwheel
Cartwheel offers mental health support to students in order to help schools regain balance in the midst of the student mental health crisis.
201-500 employees
Funding
Current Stage
Growth StageTotal Funding
$55.17MKey Investors
Menlo Ventures
2025-08-18Series B· $35.17M
2023-09-26Series A· $20M
Leadership Team
Joe English
Co-Founder and CEO
Daniel Tartakovsky
Co-Founder and COO (We're Hiring!)
Recent News
General Catalyst
2025-12-08
generalcatalyst.com
2025-12-08
Company data provided by crunchbase