Sales Enablement Manager

Summary

Join Cartwheel, a company building a mental health program for kids, as their Sales Enablement Manager. Drive revenue growth in healthcare and education by equipping sales teams with the right tools, training, and insights. Design and deliver onboarding programs, build training curricula, and develop role-playing scenarios. Create and maintain sales collateral, refine pitch decks, and ensure content remains current. Analyze sales performance data, refine sales methodologies, and collaborate with other teams for seamless processes. This is a remote, full-time, salaried position with regular in-person team retreats.

Requirements

• 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
• 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

Responsibilities

• 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

Preferred Qualifications

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

Benefits

• 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