Senior Director, Head of Scaled Sales · Dropbox

Sat, 25 Apr 2026 12:10:33 GMT
Sales

Dropbox · Remote - Canada: Select locations · remote

Dropbox is seeking a Senior Director, 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.

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.

Requirements:

12+ years of experience in SaaS sales, revenue strategy, growth, or go-to-market leadership, including experience in scaled, high-velocity, or hybrid PLG and sales-assisted environments.

Proven track record designing or scaling segmentation, coverage, or targeting models that improved conversion, efficiency, or expansion outcomes.

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.

Demonstrated success building new programs, motions, or teams from the ground up in ambiguous, fast-changing environments.

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.

Preferred Qualifications:

Experience building or leading a PLG-assist or sales-assisted growth motion in a multi-product SaaS company.

Experience applying AI or automation to improve sales productivity, targeting precision, or customer engagement outcomes.

Background in both strategy and execution, with comfort moving between high-level GTM design and hands-on operational problem solving.

Familiarity with customer lifecycle marketing, product signals, and expansion motions within self-serve or managed funnels.

Experience in environments undergoing GTM transformation, including introducing new motions, redefining ownership boundaries, or building new operating models.