Director of Revenue Operations

Who The Flip Is Flip?

Ever call your favorite eCommerce brand, and have a crazy good Voice AI answer? That’s Flip. Hundreds of brands from Brooklinen, Princess Polly, and Hexclad Cookware, to Tory Burch, Belk and the NFL trust Flip to have millions of phone calls with their customers every year.

We’ve built our company on the idea that the best way to grow is to have a reference list as long as our customer list, and a constant belief that the team is the best thing we’ve built. Both are true today and increasingly so every day.

Many on our team would tell you this is their favorite place they’ve ever worked, and the hardest they’ve ever worked. It’s ideal for people who want to go all-in, do the work, ride the roller coaster, and have a great Flippin time doing it. We’re a small and mighty team of 50 today with offices in NYC, LA, and the UK.

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

Our current stack reflects a scrappy, build-what-we-need approach and is used end-to-end — from lead intake through billing and revenue reporting:

• 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

• 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
• 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