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.
- 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.
- 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.
US Zone 1
This role is not available in Zone 1
Skills Required
- 12+ years of experience in SaaS sales, revenue strategy, or go-to-market leadership
- Proven track record designing or scaling performance improvement models
- Experience with analytics, data science, and sales operations
- Strong analytical skills for data-driven decisions
- Success in building new programs in fast-changing environments
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Employees describe pay and bonuses as competitive and performance-driven.
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What We Do
We're a global community of bold visionaries and resourceful doers who are shaping the future of Dropbox—and with it the future of work. Our Virtual First model combines the flexibility of a distributed workplace with the power of human connection, making space for both meaningful work and meaningful relationships. With our start-up mindset and enterprise-level opportunities, you can be who you are and grow into who you’re meant to be. Here, you can own your impact to make work more intuitive, joyful, and human—for you as a Dropboxer and for hundreds of millions of people worldwide. If you're ready to push boundaries—and yourself—Dropbox is ready for you.
Why Work With Us
We believe people do their best work when empowered with autonomy and harmony, and we understand there’s no substitute for human connection. Our Virtual First model combines the flexibility of remote work with the power of in-person collaboration to create the best of both worlds: a distributed workplace, anchored in community.
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