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Flip has scaled quickly by being scrappy, pragmatic, and execution-focused. Our GTM and revenue systems were built to help us move fast and get to where we are today. Now, we’re ready for the next chapter. We’re looking for a Director of Revenue Operations who enjoys rolling up their sleeves, operating autonomously, and taking something that works and making it truly scalable. This role is for someone who doesn’t wait for a roadmap. You’ll proactively design, evolve, and operate the systems that power our GTM engine—often before the organization realizes a change is needed. Your job is to make revenue mechanics feel invisible to the rest of the company by anticipating issues, eliminating friction, and turning GTM data and analytics into a tailwind rather than a headwind.
Job Responsibility:
Own the end-to-end revenue operating system: Lead → Deal → Contract → Billing → Reporting
Act as the autonomous owner of GTM mechanics across Sales and Customer Success
Own the GTM system of record (currently HubSpot), with permission and expectation to challenge, evolve, or replace tools as needed
Ensure contracts and sold line items translate cleanly into billable revenue
Partner with Finance to deliver clean, system-driven invoicing and revenue visibility
Own forecasting inputs, pipeline hygiene, and GTM data integrity
Partner with Data to turn GTM analytics into a tailwind for day-to-day decision-making
Identify friction before it becomes a blocker—and fix it decisively
Take what’s been built to date and level it up for the next phase of growth
Requirements:
3–6 years experience in Revenue Operations, GTM Operations, or similar roles, with meaningful ownership of systems and processes
Experience helping scale revenue systems in a fast-growing B2B SaaS environment
Strong understanding of CRM systems, billing mechanics, and forecasting
Comfort working close to the data using SQL and modern analytics tooling
Ability to partner deeply with Finance and Data without needing translation
Low-ego, high-ownership collaboration style
Comfort balancing hands-on execution with long-term system design
You enjoy getting your hands dirty and improving imperfect systems
You operate comfortably with high autonomy and minimal direction
You think ahead of the team and are rarely surprised
You take pride in solving problems before they surface
You’re technically fluent and curious, even if you’re not an engineer
You’re comfortable reasoning about data flows, transformations, and system dependencies
You care more about outcomes than tools
What we offer:
Comprehensive healthcare and unlimited vacation, including a mandatory half week for everyone over July 4, and a full week off at the end of the year
Bonus and/or commission as well as equity, in accordance with company policy