Director, Head of Scaled Sales

Role Description

Dropbox is seeking a Head of Scaled Sales to build and lead our sales-assisted growth motion from the ground up. This is a foundational leadership role for an entrepreneurial builder who is energized by creating a new motion from 0 to 100 and pairing product-led growth with the right sales touch to accelerate conversion, expansion, and efficiency. This leader will design the segmentation, coverage, and experimentation systems that determine when, where, and how sales engages self-serve customers, while partnering closely with marketing, data science, and sales analytics to turn signals into action. The right candidate will bring a strong operator mindset, deep fluency in PLG and hybrid GTM models, and a clear point of view on how to balance AI and human judgment to improve outcomes at scale.

Responsibilities

• Build a self-serve segmentation model that identifies the right customers for the right sales motion, maximizing cost efficiency, conversion, and speed through the funnel.
• Design and implement a highly efficient coverage model that introduces sales engagement at the optimal point in the customer journey.
• Partner closely with data science and sales analytics to develop and operationalize a data-driven targeting strategy.
• Work cross-functionally with marketing to deliver targeted campaigns to the right customers at the right time with the right message, improving take rates and product expansion.
• Define how AI should be deployed across the scaled sales motion to improve productivity and business outcomes, while making sound decisions about where human engagement adds the most value.
• Build and run a strong experimentation framework that enables rapid testing, learning, and iteration across segmentation, outreach, coverage, and conversion strategies.
• Establish clear operating rhythms, performance metrics, and diagnostic frameworks to understand business drivers and inform resourcing and investment decisions.
• Lead execution with a strong bias for action, using data to continuously improve funnel performance and scale a repeatable sales-assisted PLG motion.

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