dropbox

Director, Head of Scaled Sales

Apply Now

At a Glance

Location
Canada: Select locations
Work Regime
remote
Employment
employment_required
Experience
12+ years
Posted
2026-04-24T09:38:06-04:00

Key Requirements

Required Skills

Data Science

Domain Knowledge

  • Automation
  • Marketing
  • SaaS

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.

Experience designing and evaluating experimentation frameworks to test GTM hypotheses and improve business performance over time.

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

Responsibilities

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.

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.