Director of RevOps

Director of Revenue Operations

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 A Street Ventures, Menlo Ventures, Reach Capital, General Catalyst, Box Group, and Able Partners, and we're looking for mission-driven teammates to join our team.

We're hiring a Director of Revenue Operations to own the systems, data, and processes that underpin our revenue engine, including school district sales, marketing, school success and government partnerships teams. This is a build-and-run role. You'll inherit a team and a tech stack, and you'll be responsible for making both work better. That means being a strong systems architect who can evaluate and evolve our Salesforce environment and add-on tooling, a hands-on team leader who develops and motivates your team, and a strategic partner to revenue leadership who can connect operational data to business and technology decisions.

Reporting to the VP of Finance, you'll lead a small team spanning Salesforce administration and architecture, sales enablement, marketing operations, reporting and analytics, planning and forecasting, contract operations, and deal desk. This is a high-visibility role with direct impact on Cartwheel's top-line growth.

Role type: W2, Full-Time, Salaried position

Location:

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

Salary range: $185,000–$215,000 including base salary and annual bonus, plus competitive equity compensation package

Reports to:

VP of Finance

• Own Salesforce as Cartwheel's CRM of record — make architecture decisions, enforce data standards, and drive adoption across Sales, Marketing, and Customer Success
• Evaluate, implement, and manage the add-on tooling ecosystem (including Hub Spot, Churn Zero, Star Bridge, Agile, and others), ensuring each tool is optimized and high-ROI
• Manage internal team and external contractor to implement integrations, automations, rules, and reporting as needed

• Design and maintain scalable processes across the full revenue lifecycle — pipeline management, forecasting, deal desk, contract operations, and renewal tracking
• Partner with Sales, Marketing, and Customer Success leadership to improve productivity, reduce friction, and surface the data they need to make decisions
• Support commissions tracking, territory and quota management, and pricing operations

• Build toward a single source of truth for GTM data — eliminating fragmentation across systems and enabling reliable attribution and forecasting
• Partner with Data team to ensure consistent data pipelines are in place between GTM tooling and company-wide data warehouse infrastructure
• Build and maintain dashboards and KPI review cadence that give revenue leadership real-time visibility into pipeline health, conversion, retention, and performance against plan
• Support Revenue leadership in understanding highest efficiency channels and activities to continue to drive CAC and LTV

• Manage and develop Revenue Operations team members
• Set clear priorities and build team capacity
• Create a culture of high standards, continuous improvement, and service mindset towards our GTM teammates
• Build relationships and trust with Revenue Leadership and GTM team members

We set a high bar for this role. The right candidate is both a technical operator and a strategic leader — someone who can get their hands dirty in Salesforce while also setting the vision for how Rev Ops supports Cartwheel's next phase of…