Vice President, Revenue Operations

Open Role

Vice President, Revenue Operations

Remote - Canada: Select locations

Remote

Business Strategy & Ops

Full Time

Dropbox is a Virtual First company. For this role, we are currently only authorized to hire candidates from the following provinces: Alberta, British Columbia, Ontario, and Saskatchewan.

Role Description

Dropbox is seeking a Vice President of Revenue Operations to define and lead the operating strategy for the company’s global B2B go-to-market organization. This executive will be responsible for building a high-performing, scalable revenue engine that enables predictable and efficient growth across SMB, Mid-Market, and Enterprise segments while supporting Dropbox’s evolution across product-led, sales-assisted, and enterprise motions.

This leader will serve as a key strategic partner to the Chief Business Officer and broader executive leadership team, translating company strategy into the operating model, planning frameworks, systems, insights, and execution mechanisms required to deliver durable growth. The role will own Revenue Operations and Marketing Operations across the customer lifecycle, ensuring tight alignment between demand generation, pipeline creation, sales execution, retention, expansion, and overall revenue performance.

The VP of Revenue Operations will have enterprise-wide accountability for revenue planning, forecasting, segmentation, capacity and coverage strategy, incentives, GTM systems, analytics, operating cadence, and revenue productivity. This leader will play a central role in shaping how Dropbox allocates resources, evaluates performance, scales new products and motions, and modernizes its GTM organization through data, automation, and AI.

Responsibilities

• Define and lead Dropbox’s global revenue operating strategy, ensuring the company’s GTM model is designed to support long-term growth, efficiency, and increasing enterprise complexity
• Serve as a strategic advisor to the Chief Business Officer and executive leadership team, bringing data-driven insights and recommendations to critical decisions around growth, investment, resource allocation, organizational design, and GTM strategy
• Own the end-to-end revenue operating model across Sales, Marketing, Customer Success, and Support, including segmentation, coverage models, territory architecture, role design, operating rhythms, and cross-functional accountability
• Lead company-wide annual and long-range revenue planning, including bookings targets, quota strategy, capacity and workforce planning, territory design, productivity assumptions, investment scenarios, and resource allocation
• Establish a best-in-class forecasting and pipeline management framework that increases predictability, strengthens executive visibility, and enables earlier intervention against business performance risks
• Define and evolve the company’s revenue performance architecture, including the KPIs, operating cadences, inspection mechanisms, and executive business reviews used to assess growth, productivity, efficiency, retention, and expansion
• Lead Revenue Operations across the full customer lifecycle, creating scalable and integrated processes from demand generation and lead management through opportunity conversion, renewal, expansion, and customer growth
• Partner with Marketing leadership to oversee Marketing Operations and ensure strong alignment between demand generation investments, pipeline creation, segmentation, campaign performance, and downstream revenue outcomes
• Partner closely with Finance on revenue strategy and planning, pricing and packaging operations, investment allocation, deal governance, incentive compensation, and performance management
• Partner with Product and GTM leadership to define the operating strategy for new products, new customer segments, pricing changes, packaging evolution, and emerging sales motions
• Own the strategy and evolution of Dropbox’s GTM technology ecosystem, ensuring systems, data architecture, automation, and workflows scale effectively with the business
• Lead the adoption of AI across Revenue Operations and the broader GTM organization, identifying opportunities to fundamentally improve seller productivity, forecasting, customer targeting, planning, decision-making, and operational efficiency
• Simplify legacy processes, systems, and organizational structures where needed, driving enterprise-wide transformation and change management across a complex stakeholder environment
• Build, lead, and develop a world-class Revenue Operations organization, including strong leadership succession, organizational design, talent development, and clear accountability across teams
• Represent Revenue Operations in executive-level and company-wide planning forums, serving as a trusted voice on GTM performance, risks, opportunities, and operating priorities

Requirements

• 15+ 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

The range listed above is the expected annual salary/OTE (On-Target Earnings) for this role, subject to change.

Salary/OTE is just one component of Dropbox’s total rewards package. All regular employees are also eligible for the corporate bonus program or a sales incentive (target included in OTE) as well as stock in the form of Restricted Stock Units (RSUs).

Read more about our benefits here.

Company Description

Dropbox isn’t just a workplace—it’s a living lab for designing a more enlightened way of working. We’re a global community of bold visionaries and resourceful doers shaping the future of Dropbox and, in turn, the future of work. Our Virtual First model combines the autonomy of a distributed workplace with the power of human connection, creating space for meaningful work and lasting relationships. With a startup mindset and enterprise-level opportunities, we expect Dropbox employees to think critically, stay curious, and use modern tools, including AI, to improve how work gets done. Here, you can be who you are and grow into who you’re meant to be. You own your impact, helping make work more intuitive, joyful, and human for yourself and hundreds of millions of people worldwide. If you’re ready to push boundaries and challenge yourself, Dropbox is ready for you.

Team Description

The Dropbox Business Strategy & Operations team unlocks the company's full potential by driving strategic initiatives and promoting operational excellence. We combine analytical rigor with creative problem-solving to tackle Dropbox’s biggest opportunities and challenges across all business functions. Partnering closely with Product, Engineering, Sales, Marketing, and Finance, we translate our strategic vision into actionable plans that foster growth, optimize performance, and facilitate informed decision-making. Our work shapes th