Dropbox

Director, Head of Scaled Sales

Remote - Canada: Select locations · Director

Sponsorship not specifiedDetected 5 days ago

Data ScienceA/B TestingSalesLeadershipCommunication

About the role

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.
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.

Partner closely with data science and sales analytics to develop and operationalize a data-driven targeting strategy.
Lead execution with a strong bias for action, using data to continuously improve funnel performance and scale a repeatable sales-assisted PLG motion.
Dropbox is seeking a Head of Scaled Sales to build and lead our sales-assisted growth motion from the ground up.

Experience partnering closely with analytics, data science, marketing, and sales operations teams to translate insights into GTM execution.
Strong analytical fluency with the ability to define success metrics, inspect performance, identify root causes, and make data-driven decisions.
Experience designing and evaluating experimentation frameworks to test GTM hypotheses and improve business performance over time.
Strong executive communication and cross-functional influence skills, with the ability to align stakeholders around new ways of working.

Experience applying AI or automation to improve sales productivity, targeting precision, or customer engagement outcomes.
Familiarity with customer lifecycle marketing, product signals, and expansion motions within self-serve or managed funnels.

Design and implement a highly efficient coverage model that introduces sales engagement at the optimal point in the customer journey.
Build and run a strong experimentation framework that enables rapid testing, learning, and iteration across segmentation, outreach, coverage, and conversion strategies.

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.
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.

This listing is sourced directly from Dropbox's careers page and normalized into a canonical job model.