[Hiring] Director of Revenue Operations @Cartwheel

Role Description

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
• 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

Qualifications

• Proven experience supporting a high-functioning enterprise sales organization
• 7+ years of experience in Revenue Operations or Sales Operations, with at least 2 years in a people management role
• Deep Salesforce expertise — you've owned architecture decisions, not just configured fields; Salesforce Admin certification strongly preferred
• Demonstrated ability to evaluate and rationalize a GTM tech stack, with experience managing tools like Outreach, HubSpot, or similar
• Strong analytical and data skills, with experience connecting CRM data to BI tools (Looker, Tableau, or equivalent)
• Experience designing and maintaining GTM processes end-to-end: pipeline management, forecasting, deal desk, and renewals
• Track record of building and enabling high-performing GTM teams through process clarity, tooling, and documentation
• Strong cross-functional communicator who can partner with Sales, Customer Success, Marketing, and Finance leadership

Requirements

• Experience in a B2B SaaS company at the Series B or C stage, ideally in a high-growth environment
• Background in employer-sponsored healthcare, ed-tech, or other mission-driven industries
• Experience with Looker or SQL for building and maintaining GTM dashboards
• Familiarity with K-12 district sales cycles, or other complex GTM motions
• Proven ability to build RevOps infrastructure from a reactive to a proactive posture
• Experience with Gong or similar conversation intelligence tools
• Experience with Starbridge, particularly in an edtech context

Benefits

• Mission-oriented and inclusive colleagues who will go to bat for you
• Competitive compensation
• Generous PPO medical, vision, and dental/ortho coverage
• Life Insurance
• Generous paid time off, including company closure from Christmas-New Years (12/25-1/1)
• Paid holidays and sick leave
• Paid parental leave
• 401K with employer match
• Meaningful equity ownership stake in Cartwheel
• Flexible and remote role with regular in-person retreats
• Annual learning stipend
• Laptop