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 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
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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
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Lead annual and quarterly revenue planning processes, including bookings targets, quota setting, capacity planning, territory design, and ramp assumptions
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Establish forecasting rigor, pipeline management processes, inspection cadences, and performance management standards that improve visibility and predictability across the business
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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
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Lead revenue operations across the customer lifecycle, from lead routing and opportunity management through renewal and expansion, ensuring scalable processes, governance, and execution excellence
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Partner with Data Science on analytical support and insights, experimentation and cadence for biz performance updates
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Partner with Finance on revenue planning, pricing operations, discounting frameworks, deal governance, sales compensation, and incentive design to support growth and operational discipline
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Partner with Customer Success and Support leadership to improve retention, renewal, and expansion outcomes through operational insights, reporting, and process optimization
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Enable GTM readiness and operational execution for new product launches, packaging changes, pricing updates, and growth initiatives
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Deliver executive-level reporting, business reviews, and performance insights that support decision-making across revenue leadership
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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
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).
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 the future of Dropbox by leading cross-functional business planning, developing insights that guide corporate and business unit strategies, creating systems and processes that power scalable success. If you're passionate about strategic thinking, solving complex problems, and making an impact through collaboration, join our Business Strategy & Operations team.
Virtual First
Dropbox’s Virtual First way of working is designed to help people do their best work with flexibility, autonomy, and connection. Day to day, teams work remotely with nonlinear schedules and core collaboration hours that support deep focus and individual working styles. We prioritize asynchronous communication to improve clarity, respect deep work time, and reduce unnecessary meetings. While remote work is the primary experience for our employees, we also prioritize intentional, in-person connection. We bring teams together through regular team gatherings, on-demand workspaces, and Dropbox Neighborhood events in order to strengthen team cohesion, foster creativity, and enhance momentum. Virtual First is built to provide the same access to opportunity, growth, and impact for everyone, regardless of location.
This role requires travel to offsites and various other team gatherings (approximately 5-10% of the year or 2-3 days per quarter). We provide advance notice when possible and encourage candidates to discuss any accommodation needs during the interview process.
AI Fluency
- Ownership: You use AI responsibly by protecting data, applying sound judgment, and taking accountability for the quality and accuracy of your work.
- Experimentation: You explore new AI capabilities and apply them to improve workflows within approved tools and practices.
- Leverage: You use AI to enhance thinking, improve efficiency, and increase your impact and your team’s.
- Learning: You stay current on emerging AI tools and trends, continuously build your skills, and share what you learn with others.
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.