Director, Head of Scaled Sales

Role Description

Dropbox is seeking a Head of Scaled Sales to build and lead a sales-assisted growth motion from the ground up. This is a foundational leadership role for an entrepreneurial builder energized by creating new motions and pairing product-led growth with strategic sales engagement to accelerate conversion, expansion, and efficiency.

You will design segmentation, coverage, and experimentation systems that determine when, where, and how sales engages self-serve customers. Partner closely with marketing, data science, and sales analytics to convert signals into action. This role requires a strong operator mindset, deep fluency in PLG and hybrid go-to-market models, and a clear perspective on balancing AI and human judgment to improve outcomes at scale.

Key Responsibilities

• Build a self-serve segmentation model identifying the right customers for the right sales motion, maximizing cost efficiency, conversion, and funnel speed
• Design and implement an efficient coverage model that introduces sales engagement at optimal points in the customer journey
• Partner with data science and sales analytics to develop and operationalize a data-driven targeting strategy
• Work cross-functionally with marketing to deliver targeted campaigns that improve take rates and product expansion
• Define AI deployment across scaled sales to improve productivity and business outcomes, balancing automation with high-value human engagement
• Build and run a strong experimentation framework enabling rapid testing, learning, and iteration across segmentation, outreach, coverage, and conversion strategies

Salary Information

Editorial Market Estimate: $70,000–$120,000 USD annually. This is not employer-provided compensation and may vary significantly by experience, qualifications, and location.