Dropbox - Director, Head of Scaled Sales
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. • 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.
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.
Benefits
• The range listed above is the expected annual salary/OTE (On-Target Earnings) for this role, subject to change.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).
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