ABOUT CARTWHEEL
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 shouldnt 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, BoxGroup, and Able Partners, and were looking for mission-driven teammates to join our team.
THE ROLE
Were 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. Youll inherit a team and a tech stack, and youll 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, youll 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 Cartwheels 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
WHAT YOULL DO
Systems Architecture & Tech Stack
- Own Salesforce as Cartwheels 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 HubSpot, Churn Zero, StarBridge, 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
GTM Operations & Enablement
- 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
Data & Reporting
- 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
Team Leadership
- 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
WHO YOU ARE
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 RevOps supports Cartwheels next phase of growth.
Required
- 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 - youve 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
Nice to Have
- 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
Youll Thrive Here If You
- Believe that operational infrastructure is a strategic lever, not just a support function
- Are energized by ambiguity and find satisfaction in bringing order to complexity
- Hold yourself and your team to high standards without losing sight of the mission
- Care about the work Cartwheel does for students and are motivated by the chance to build something that matters
Please apply even if you dont meet all of the criteria. If your past experience doesnt perfectly match the job description, but you bring other relevant experience or skills, wed still love to hear from you. You may be a great fit!
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, youll have:
- 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