- 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

- 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 current 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

Benefits

- On-site fitness and meditation classes

- Commuter subsidies
- Medical, dental, and vision coverage

- We offer a generous company contribution toward individual medical, dental, and vision insurance coverage, including contributions toward dependent premiums

- Start building a successful 401K retirement plan with our dollar for dollar contribution match, up to $1,500 per quarter to a maximum of $6,000 per calendar year

- Keep sharing and collaborating with friends and family even when you’re not at work with free Dropbox space for your whole crew

- Take the vacation you’ve always dreamed of with up to four consecutive weeks of paid time off

- Celebrate common holidays without your paycheck taking the hit with 11 company paid holidays

- Each Dropboxer has access to 32 hours of paid volunteer time off each year that they can use to support the causes close to their hearts

- We regularly offer panels and seminars featuring the best minds in tech, talent, diversity, and beyond that any Dropboxer can attend from the comfort of their home

- No two Dropboxers are the same, and their benefits shouldn’t be either.



Our Perks allowance empowers employees to customize their benefits in line with what really matters to them- Strong understanding of SaaS business models, revenue motions, and key operational drivers across acquisition, expansion, and retention

- 12+ years of experience in Revenue Operations, Sales Operations, GTM Operations, Finance, or related functions within a scaled SaaS or product-led growth company

- Track record of building, developing, and leading high-performing revenue operations teams in a fast-paced, evolving environment

- Deep expertise in forecasting, revenue planning, territory design, quota management, sales productivity, incentive compensation, and pipeline management

- Judgment: Evaluate information and make decisions in complex situations

- Adaptability: Learn, adjust, and stay effective through change

- Strong cross-functional leadership skills with the ability to influence senior stakeholders across Sales, Finance, Product, Marketing, and Customer organizations

- Awareness: Understand yourself and others

- Experience supporting organizations through significant growth and GTM evolution, including PLG, sales-assisted, and enterprise motions
- 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

- 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:

- Connection: Communicate, collaborate, and build trust

- Strong analytical and problem-solving capabilities, with extensive experience leveraging data to drive operational and business decisions

- Proven experience leading revenue operations for multi-segment B2B organizations across SMB, Mid-Market, and Enterprise customer segments

- Demonstrated ability to identify operational challenges and implement scalable, data-driven solutions that improve business performance

- Durable Skills:
- 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

📌 Senior Director of Revenue Operations (Canada)
🏢 Dropbox
📍 Canada