Director of Revenue Operations

Flip is a leading Voice AI platform that partners with eCommerce brands such as Brooklinen, Princess Polly, Hexclad Cookware, Tory Burch, Belk, and the NFL. Our team builds and scales systems that handle millions of customer interactions each year. What You’ll Do 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. Current GTM Stack HubSpot (current CRM / GTM system of record) Matillion Omni SQL-based analytics and transformations This stack is not sacred, and you’ll have full latitude to evolve or rethink it over time. That said, you should be comfortable operating in this type of environment on day one. If working close to systems like this — understanding how data flows from lead to deal to billing — isn’t something you enjoy or feel confident doing, this is probably not the right role. Your Core Responsibilities 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 Who You Are 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 You Bring 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 More About Us We’re international, spanning the US, UK, and Canada We’ve raised +$30M to date including our recent $20M Series A — backed by Ridge, Next Coast, ScOp, Bullpen Capital, Data Point and Forum Ventures, as well as founders & executives from Amazon Alexa, Ada, Attentive, and Simon Data 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 In office, 5 days/week #J-18808-Ljbffr