Director, Head of Scaled Sales

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. 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

• 10+ 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.

Compensation

US Zone 1

$234,200—$316,800 USD

US Zone 2

$210,800—$285,200 USD

US Zone 3

$187,300—$253,500 USD

The range(s) listed above is the expected annual salary/OTE (On-Target Earnings) for this role, subject to change. Please note, OTE are for sales roles only.

Salary/OTE is just one component of Dropbox's total rewards package. All regular employees are also eligible for the corporate bonus program or a sales incentive (target included in OTE) as well as stock in the form of Restricted Stock Units (RSUs).

Dropbox takes a number of factors into account when determining individual starting pay, including job and level they are hired into, location/metropolitan area, skillset, and peer compensation. We target most new hire offers between the minimum up to the middle of the range.

Dropbox uses the zip code of an employee's remote work location to determine which metropolitan pay range we use. Current US Zone locations are as follows:

• US Zone 1: San Francisco metro, New York City metro, or Seattle metro
• US Zone 2: California (outside SF metro), Colorado, Connecticut (outside NYC metro), Delaware, Illinois (Chicago metro), Indiana (Chicago metro), Maryland, Massachusetts, Michigan (Chicago metro), New Hampshire, New Jersey (outside NYC metro), New York (outside NYC metro), Oregon, Pennsylvania (D.C. metro), Pennsylvania (outside NYC metro), Texas (Austin metro) Virginia (DC metro), Washington (outside Seattle metro), Washington DC metro, West Virginia (DC metro), Wisconsin (Chicago metro)
• US Zone 3: All other US locations

Dropbox is a Virtual First company and is open to hiring candidates in all authorized locations.