# Senior Director, Head of Scaled Sales **Company**: Dropbox **Location**: Remote - Canada: Select locations **Work arrangement**: remote **Experience**: senior **Job type**: full-time **Category**: Sales **Industry**: Technology **Apply**: https://job-boards.greenhouse.io/dropbox/jobs/7848539?utm_source=yubhub.co&utm_medium=jobs_feed&utm_campaign=apply **Canonical**: https://yubhub.co/jobs/job_a6cfb5ba-574 ## 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. 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: - 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: - 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 --- Source: [Apply at job-boards.greenhouse.io](https://job-boards.greenhouse.io/dropbox/jobs/7848539?utm_source=yubhub.co&utm_medium=jobs_feed&utm_campaign=apply)