# Senior Director, Head of Scaled Sales

**Company**: Dropbox
**Location**: Remote - US: Select locations
**Work arrangement**: remote
**Experience**: executive
**Job type**: full-time
**Salary**: US Zone 2 $251,700-$340,500 USD
**Category**: Sales
**Industry**: Technology

**Apply**: https://job-boards.greenhouse.io/dropbox/jobs/7848536
**Canonical**: https://yubhub.co/jobs/job_8282041d-2fe

## Description

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.

Key responsibilities include:

- Building a self-serve segmentation model that identifies the right customers for the right sales motion, maximizing cost efficiency, conversion, and speed through the funnel.

- Designing and implementing a highly efficient coverage model that introduces sales engagement at the optimal point in the customer journey.

- Partnering closely with data science and sales analytics to develop and operationalize a data-driven targeting strategy.

- Working 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.

- Defining 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.

- Building and running a strong experimentation framework that enables rapid testing, learning, and iteration across segmentation, outreach, coverage, and conversion strategies.

- Establishing clear operating rhythms, performance metrics, and diagnostic frameworks to understand business drivers and inform resourcing and investment decisions.

Requirements include:

- 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 include:

- 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.

## Skills

### Required
- SaaS sales
- Revenue strategy
- Growth
- Go-to-market leadership
- Segmentation
- Coverage
- Targeting models
- Analytics
- Data science
- Marketing
- Sales operations
- Experimentation frameworks
- AI
- Automation
- Customer engagement outcomes

### Nice to have
- PLG-assist
- Sales-assisted growth motion
- Multi-product SaaS company
- Customer lifecycle marketing
- Product signals
- Expansion motions