Director of Revenue Operations

Join Cartwheel to help tackle the student mental health crisis.

Please ensure you read the below overview and requirements for this employment opportunity completely.

Kids spend most of their days in the classroom. And teachers and staff, who play a vital role in their development, are often the first to notice when something is off.

But with 1 in 5 young people struggling with mental health, schools are getting crushed by a downward spiral in student crises and staff burnout.

With large increases in federal funding for schools and the rise of telehealth, schools are reimagining what mental health support can look like.

Cartwheel is an early-stage startup building technology-enabled mental health services that put schools at the center. We see our role as supporting on-campus counselors, psychologists, and school social workers who see kids every 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

As our Director of Revenue Operations, you'll architect the processes, platforms, and insights that will power our growth engine.

You’ll work across our sales, marketing, and school success teams, directly impacting our ability to scale and ultimately improve mental health support for students across the country.

Role type : Full-time

Location : Remote with quarterly in-person team retreats and co-locating as needed, especially as we get to know each other.

WHAT YOU’LL DO

RevOps Strategy

• Collaborate with go-to-market leadership and the CEO to set and achieve revenue targets
• Drive cross-functional initiatives to improve customer acquisition, retention, and expansion
• Implement best practices for revenue forecasting and reporting
• Build and lead a Rev Ops team that will help our revenue teams rapidly scale

Technology and Data Management

• Architect a revenue technology stack that will scale with rapid growth, knitting together key platforms such as Salesforce and Hubspot
• Develop and manage comprehensive reporting dashboards to provide insights
• Manage tools for contract management, quoting, and e-signature processes
• Ensure data integrity and hygiene across systems

Process Optimization

• Design, implement, and continually improve Rev Ops processes
• Oversee documentation, training, and quality assurance of Rev Ops processes
• Manage a robust lead management and routing system
• Support seamless lead handoff between marketing, sales, and success

Analytics and Reporting

• Analyze trends, gaps, and opportunities in the revenue cycle
• Help develop key performance indicators (KPIs)
• Oversee forecasting and reporting
• Help develop and track impact of sales and marketing campaigns

Contracting and Proposals

• Oversee contracting processes in collaboration with our legal team
• Oversee efforts to source and win Requests for Proposals and key funding opportunities
• Ensure all revenue operations comply with relevant regulations and industry standards

WHO YOU ARE

• 7+ years of experience in Revenue Operations
• Fluency in key go-to-market platforms (e.g., Salesforce, Hubspot) with strong knowledge of tech-stack architecture, implementation, and optimization
• Analytical and problem-solving skills with a deep understanding of go-to-market metrics.
• Excellent process orientation. Ability to analyze, design, optimize, and communicate processes that can scale with rapid growth.
• Exceptional project management skills with the ability to juggle multiple priorities
• Ability to leverage data to identify and optimize the customer lifecycle from lead generation through retention and renewal
• Excellent communication and relationship development skills

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 :

• Team-based culture with mission-driven colleagues who will go to bat for you
• Compensation range of $130-160K plus meaningful equity ownership stake and benefits
• Flexible paid time off
• Remote work environment with regular in-person team retreats
• 401K with employer match
• $500 annual educational stipend
• Macbook

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.

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