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Senior Director, Head of Scaled Sales

224k – 341kUnited StatesRemote10+ YOE
Summary

Build and lead Dropbox's sales-assisted PLG motion from scratch, designing segmentation, coverage, and experimentation systems while partnering with marketing, data science, and analytics to drive conversion and expansion at scale.

About the role

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.
Skills
SaaS salesrevenue strategygo-to-market leadershipPLGsales-assisted growthsegmentation modelscoverage modelstargeting modelsdata sciencesales analyticsexperimentation frameworksAI for sales productivity
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