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
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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
To apply: https://weworkremotely.com/remote-jobs/dropbox-senior-director-revenue-operations
