---
title: 'Director of RevOps at Cartwheel'
canonical: 'https://feeny.ai/job/director-of-revops-cartwheel-cambridge-p8v9nv8wzmsx'
type: 'job'
last_seen: '2026-09-12'
---

# Director of RevOps at Cartwheel

- **Company:** Cartwheel
- **Location:** Cambridge, MA
- **Compensation:** $185k–$215k
- **Employment:** full-time
- **Work type:** remote
- **Posted:** 2026-08-07
- **Last confirmed live:** 2026-09-12
- **Apply:** https://jobs.gem.com/cartwheel-1/am9icG9zdDrRDQmyF7V5BDwDin3owaaz

## Job description

## 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 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, BoxGroup, and Able Partners, and we're looking for mission-driven teammates to join our team.

## THE ROLE

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

## WHAT YOU'LL DO

Systems Architecture & Tech Stack

- 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 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 Cartwheel's 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 — 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

## 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 You'll 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 don't meet all of the criteria. If your past experience doesn't perfectly match the job description, but you bring other relevant experience or skills, we'd 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, you'll 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

## About Cartwheel

## Company Overview
- **One-liner**: Cartwheel is a trusted mental health partner to schools, providing rapid access to evidence-based therapy and psychiatry for students.
- **Entity Type**: Private (Post-Series B)
- **Headquarters**: Cambridge, Massachusetts, United States
- **Founded**: 2022
- **Founders**: Joe English (CEO) and one other co‑founder (COO, name not publicly disclosed)

## Core Business
- **Primary industry**: Mental Health Care / Telehealth for K-12 schools
- **Target customers**: School districts, students, and families (B2B through schools, B2C through families)
- **Mission**: To help schools build stronger mental health programs and ensure students can thrive in school, at home, and in life.

## Products & Services
- **Cartwheel Platform**: A school‑partnered mental health service offering individual therapy, group therapy, medication management, and parent guidance, delivered virtually by licensed clinicians. Includes care coordination and integration with school’s Multi‑Tiered System of Supports (MTSS).

## Market Standing
- **Valuation/Market Cap**: Not disclosed (private)
- **Key Metric**: Total Funding **$55.2M** (Series B of $35.2M led by A‑Street Ventures and Menlo Ventures, Sep 2025; Series A $20M led by Menlo Ventures, Sep 2023)
- **Notable Investors/Partners**: Menlo Ventures, A‑Street Ventures; partnerships with numerous school districts.
- **Growth Signals**: 191 employees (yearly growth +41.9%), active job postings increasing (+58.3% monthly), 92% of students report feeling better after care.

## Competitive Advantages
- **Rapid access**: average 7 days to first appointment, no waitlists.
- **School‑embedded model**: teachers and staff refer students, care coordinators handle logistics.
- **Evidence‑based care** with measurable outcomes (92% improvement).
- **Bilingual care coordinators** and licensed clinicians.
- **Strong technology platform** for care coordination and telehealth.

## Strategic Focus
- Expanding partnerships with school districts nationwide (recent roles for GM Statewide Partnerships, Customer Success Managers).
- Building out insurance network (Medicaid, commercial) to maximize access.
- Scaling clinical team and care delivery while maintaining quality.
- Improving product/tech platform to support growth.

## Why Work Here
- **Mission‑driven**: direct impact on student mental health.
- **Remote/hybrid options**: many roles are remote (therapist contractors nationwide). HQ in Cambridge, MA with in‑office/hybrid for some positions.
- **Culture**: interdisciplinary team of clinicians, school leaders, engineers, operators; described as “the best place they’ve ever worked.”
- **Growth**: rapid scale (41.9% headcount growth) offers career advancement opportunities.
- **Values**: evidence‑based, rapid access, equity, collaboration.

## Sources
1. [cartwheel.org](https://www.cartwheel.org/)
2. [cartwheel.org/about-us](https://www.cartwheel.org/about-us)
3. [LinkedIn](https://linkedin.com/company/cartwheelcare)
4. [Built In Boston](https://www.builtinboston.com/company/cartwheel)

## Other roles at Cartwheel

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- [Associate Writer](https://feeny.ai/job/associate-writer-cartwheel-cambridge-jcywxj52v7qx) — Cambridge, MA
- [Senior Writer](https://feeny.ai/job/senior-writer-cartwheel-cambridge-4yjg6seh9wcr) — Cambridge, MA
- [Mental Health Therapist, Contractor - NV / Remote](https://feeny.ai/job/mental-health-therapist-contractor-nv-remote-cartwheel-cambridge-a81a1f0dxd0h) — Cambridge, MA
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