Vice President, Revenue Operations

Dropbox; Saskatchewan; Hybrid; CAD 250,000 - 360,000; Full time

Job summary

Dropbox is seeking a Vice President of Revenue Operations to define and lead the operating strategy for the global B2B go-to-market organization. This executive will build a scalable revenue engine across SMB, Mid-Market, and Enterprise while aligning demand generation, sales execution, retention, and expansion.

The role partners with the CBO and executive team to develop operating models, systems, and analytics that enable durable growth and modernized GTM through data, automation, and AI.

Qualifications

• 15+ years of experience in Revenue Operations, Sales Operations, GTM Operations, or related functions in a scaled SaaS or product-led growth company.
• Proven experience leading revenue operations for multi-segment B2B organizations across SMB, Mid-Market, and Enterprise.

Responsibilities

• Define and lead Dropbox’s global revenue operating strategy to support long-term growth and enterprise complexity.
• Own end-to-end revenue operating model across Sales, Marketing, Customer Success, and Support with segmentation, territory and rhythm design.
• Lead annual and long-range revenue planning, including bookings targets, quota strategy, and capacity planning.
• Establish forecasting and pipeline management frameworks to improve predictability and executive visibility.
• Partner with Marketing to align demand generation, pipeline, and revenue outcomes, and with Finance on pricing and investments.
• Oversee GTM technology ecosystem and drive adoption of AI to improve seller productivity and decision-making.
• Represent Revenue Operations in executive planning forums and drive enterprise-wide transformation.

Skills

Strategic leadership

Data-driven

Cross-functional collaboration

GTM optimization

Forecasting

Tools

Salesforce

Job description

• 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.

Dropbox is an equal opportunity employer. We are a welcoming place for everyone, and we do our best to make sure all people feel supported and connected at work.