Sales Enablement Manager

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 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.

About The Role

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: Fall 2025

What You’Ll Do

Sales Training & Development

• Design and deliver 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

Who You Are

Must Have...

• 4+ years of business operations, sales operations, or related analytical role supporting revenue teams
• Excellent written and verbal communication skills 
• Advanced proficiency in CRM systems and reporting tools
• Experience leading knowledge management and ensuring adherence to best practices across the team
• Ability to analyze efficacy of sales materials and processes, iterate on potential changes, and make data-driven recommendations to Sales leadership
• Strong project management and attention to detail
• Ability to balance multiple priorities and deliver high-quality work in a fast-paced startup environment
• Ability to work collaboratively with RevOps, Marketing, Product, and Success teams

Extra Credit…

• Experience in the K-12 education technology
• 2+ years in management consulting
• 2+ years of direct sales experience
• Experience building reporting systems, forecasting models, and operational processes that support sales teams
• Experience with sales frameworks and methodologies (e.g. SPIN, MEDDPICC, Challenger)

Why You’Ll 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, you’ll have: 

• Competitive compensation between $100,000- $120,000 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. 

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