Director of RevOps

Cartwheel•Cambridge, MA

13d•$185,000 - $215,000•Remote

About The Position

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.

Requirements

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 Haves

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

Responsibilities

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
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

Benefits

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
Annual learning stipend
Laptop