Senior Director, Revenue Operations

Other Jobs To Apply

Headquarters: Remote - Canada: Select locations

Role Description

Dropbox is seeking a Head of Revenue Operations to lead and scale the operational foundation of the company's global B2B go-to-market organization. This role will be responsible for driving operational excellence across the revenue engine, enabling predictable, efficient growth across SMB, Mid-Market, and Enterprise segments. This role will also oversee Marketing Operations, ensuring alignment between demand generation, pipeline creation, and revenue outcomes across the full customer lifecycle.
This leader will own revenue planning, forecasting, revenue operations, incentives, systems, analytics, and GTM infrastructure. Partnering closely with Sales, Finance, Product, Marketing, and Customer leadership, this role will play a critical role in strengthening execution rigor, improving forecast accuracy, and enabling Dropbox to scale across products, regions, and sales motions, including product-led, sales-assisted, and enterprise.

Responsibilities

  • Own and continuously improve Dropbox's end-to-end revenue operating model, including segmentation, account coverage, territory design, role clarity, and cross-functional handoffs across Sales, Marketing, Customer Success, and Support
  • Lead annual and quarterly revenue planning processes, including bookings targets, quota setting, capacity planning, territory design, and ramp assumptions
  • Establish forecasting rigor, pipeline management processes, inspection cadences, and performance management standards that improve visibility and predictability across the business
  • Define, track, and operationalize core revenue and GTM KPIs (e.g., pipeline coverage, win rates, ACV, sales cycle, productivity, CAC, velocity, retention, and expansion), identifying performance gaps and driving operational improvements
  • Lead revenue operations across the customer lifecycle, from lead routing and opportunity management through renewal and expansion, ensuring scalable processes, governance, and execution excellence
  • Partner with Data Science on analytical support and insights, experimentation and cadence for biz performance updates
  • Partner with Finance on revenue planning, pricing operations, discounting frameworks, deal governance, sales compensation, and incentive design to support growth and operational discipline
  • Partner with Customer Success and Support leadership to improve retention, renewal, and expansion outcomes through operational insights, reporting, and process optimization
  • Enable GTM readiness and operational execution for new product launches, packaging changes, pricing updates, and growth initiatives
  • Deliver executive-level reporting, business reviews, and performance insights that support decision-making across revenue leadership
  • Build, lead, and develop a high-performing Revenue Operations organization, driving operational excellence, scalable processes, and the adoption of AI-enabled solutions that improve productivity and business performance

Requirements

  • 12+ years of experience in Revenue Operations, Sales Operations, GTM Operations, Finance, or related functions within a scaled SaaS or product-led growth company
  • Proven experience leading revenue operations for multi-segment B2B organizations across SMB, Mid-Market, and Enterprise customer segments
  • Deep expertise in forecasting, revenue planning, territory design, quota management, sales productivity, incentive compensation, and pipeline management
  • Strong understanding of SaaS business models, revenue motions, and key operational drivers across acquisition, expansion, and retention
  • Demonstrated ability to identify operational challenges and implement scalable, data-driven solutions that improve business performance
  • Strong cross-functional leadership skills with the ability to influence senior stakeholders across Sales, Finance, Product, Marketing, and Customer organizations
  • Experience supporting organizations through significant growth and GTM evolution, including PLG, sales-assisted, and enterprise motions
  • Strong analytical and problem-solving capabilities, with extensive experience leveraging data to drive operational and business decisions
  • Track record of building, developing, and leading high-performing revenue operations teams in a fast-paced, evolving environment

Preferred Qualifications

  • Proven track record implementing AI-enabled revenue solutions that deliver measurable improvements in efficiency, productivity, and business outcomes
  • Demonstrated experience owning and scaling GTM technology ecosystems, with deep expertise in Salesforce and related revenue platforms

Durable Skills

AI fluency means using these tools to amplify human judgment, not replace it. We believe people with these skills will thrive as work and technology continue to evolve:

  • Awareness: Understand yourself and others.
  • Judgment: Evaluate information and make decisions in complex situations.
  • Adaptability: Learn, adjust, and stay effective through change.
  • Connection: Communicate, collaborate, and build trust.

To learn more about why these skills matter and what the data shows about thriving through change, read this blog post from our Chief People Officer, Melanie Rosenwasser.

Compensation

To apply:

Back to blog

Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...