Sales Enablement Manager

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.

We are seeking a dynamic Sales Enablement Manager to drive revenue growth across our healthcare and education verticals. This role will be instrumental in equipping our sales teams with the tools, training, and insights needed to effectively engage healthcare providers, educational institutions, and related stakeholders. The ideal candidate will have deep experience in both industries and a proven track record of building scalable enablement programs.

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

Location: Remote in the US, with regular in-person team retreats

Start date: July 2025

Sales Training & Development

• Design and deliver comprehensive onboarding programs for new sales team hires
• Build ongoing training curricula (e.g., covering industry-specific trends and pain points, buyer personas, and sales skills in line with SPIN and Challenger models)
• Develop role-playing scenarios and objection handling frameworks
• Conduct regular skills assessments, call recording reviews, team problem solving sessions, and personalized coaching recommendations
• Provide recommendations and insights to the Head of Sales on opportunities to improve sales team learning, efficacy, and collaboration 

Content Creation & Management

• Build and maintain a library of collateral to help our team cultivate and win new business
• Refine pitch decks and demo scripts for different buyer personas, products, and markets
• Ensure content remains current with the Cartwheel brand, product, and competition
• Maintain knowledge management system (e.g., Guru) and ensure teammates are consistently and effectively using the most up-to-date materials

Process Improvement

• Partner with the Revenue Operations team to analyze sales performance data to identify strengths and opportunities across the sales team, territories, and sales stages
• Refine methodologies for prospecting, discovery, and closing

• Work closely with marketing to ensure lead quality and proper handoff processes
• Collaborate with customer success to ensure seamless opportunity handoff and develop expansion and renewal strategies

Experience

• 5+ years of sales enablement, sales training, or sales management experience
• Proven track record of designing and implementing successful enablement programs that drove measurable revenue impact
• Experience with complex B2B sales cycles in highly regulated industries involving multiple stakeholders and lengthy decision processes

Skills & Competencies

• Deep understanding of healthcare industry dynamics, including HIPAA compliance, value-based care trends, and clinical workflows OR
• Excellent presentation and facilitation skills with ability to engage diverse audiences
• Strong analytical skills with experience using CRM data to identify skill gaps and design interventions that drive measurable improvement Expert project management skills with a track record of managing multiple initiatives simultaneously
• Proficiency with CRM platforms (Salesforce preferred) and sales enablement tools

• Experience with content management systems and learning management platforms
• Familiarity with data analysis tools and ability to create meaningful reports and dashboards

Extra credit…

• Certification in sales methodology (MEDDIC, Challenger, SPIN, etc.)
• Experience with account-based marketing and selling strategies
• Previous experience selling into educational institutions

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 compensation between $120,000- $160,000 OTE, plus performance-based bonus structure
• 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 up to 2% employer match
• $500 annual educational stipend
• Opportunity to shape enablement function at a growing healthcare technology company
• Supportive, collaborative, values-driven, team culture

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.

To Apply: Please submit your resume along with a cover letter highlighting your experience in healthcare and education sales enablement. Include specific examples of programs you've built and the measurable impact they achieved.