Director, Head of Scaled Sales
Job description
Director, Head of Scaled Sales
About the role
Dropbox is looking for a leader to establish and guide a new sales-assisted growth strategy. This is a foundational position for an individual who thrives on building initiatives from inception and integrating product-led growth with sales engagement to boost conversion, expansion, and efficiency. The role involves shaping customer segmentation, coverage models, and experimentation systems to determine optimal sales interaction points with self-serve customers, working closely with marketing, data science, and sales analytics.
Key facts
What you'll do
Develop a customer segmentation framework to identify individuals suitable for sales engagement, optimizing for cost, conversion, and speed.
Create and implement an efficient coverage model that introduces sales interaction at the most opportune moments in the customer journey.
Collaborate with data science and sales analytics to build and execute a data-informed targeting approach.
Partner with marketing to launch targeted campaigns that reach the right customers with the appropriate message at the right time, enhancing engagement and product adoption.
Define the strategic use of AI within the scaled sales process to improve productivity and business results, while identifying areas where human interaction provides the greatest value.
Establish a robust experimentation framework for rapid testing, learning, and refinement of segmentation, outreach, coverage, and conversion tactics.
Define clear operational processes, performance indicators, and analytical tools to understand business drivers and guide resource allocation.
Drive execution with a focus on action, utilizing data to continuously improve funnel performance and build a repeatable sales-assisted product-led growth motion.
Requirements
A minimum of 10 years of experience in SaaS sales, revenue strategy, growth, or go-to-market leadership, including experience in scaled, high-volume, or hybrid product-led growth and sales-assisted environments.
Demonstrated success in designing or scaling segmentation, coverage, or targeting models that improved conversion, efficiency, or expansion.
Experience working collaboratively with analytics, data science, marketing, and sales operations teams to translate insights into go-to-market execution.
Strong analytical capabilities, including the ability to define success metrics, monitor performance, identify root causes, and make data-driven decisions.
Proven ability to build new programs, strategies, or teams from the ground up in dynamic and evolving settings.
Experience designing and evaluating experimentation frameworks to test go-to-market hypotheses and enhance business performance.
Excellent executive communication and cross-functional influence skills, with the ability to align stakeholders on new approaches.
Nice to have
Experience building or leading a product-led growth assist or sales-assisted growth motion within a multi-product SaaS company.
Experience applying AI or automation to enhance sales productivity, targeting accuracy, or customer engagement.
A background that combines strategic thinking with hands-on execution, comfortable moving between high-level go-to-market design and detailed operational problem-solving.
Familiarity with customer lifecycle marketing, product usage signals, and expansion strategies within self-serve or managed customer funnels.
Experience in organizations undergoing go-to-market transformation, including introducing new strategies, redefining responsibilities, or establishing new operational models.
Skills & tools
Not specified
Practical notes
US Zone 1: $234,200 - $316,800 USD
US Zone 2: $210,800 - $285,200 USD
US Zone 3: $187,300 - $253,500 USD
These ranges represent expected annual On-Target Earnings (OTE) for sales roles, subject to change. OTE includes base salary and target incentives. Total rewards also include corporate bonus program or sales incentives and Restricted Stock Units (RSUs). Starting pay is determined by job level, location, skills, and peer compensation, typically targeting the mid-point of the range. Dropbox uses employee zip codes to determine the applicable pay zone.
US Zone 1: San Francisco metro, New York City metro, 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.
This role requires approximately 5-10% travel per year (2-3 days per quarter) for offsites and team gatherings. Advance notice will be provided. Candidates with accommodation needs should discuss them during the interview process.
Dropbox operates on a Virtual First model and is open to hiring candidates in all authorized locations.
AI fluency is a core expectation, focusing on responsible use, experimentation, effective utilization, and continuous learning. Misrepresentation of skills is not permitted.
About the company
Dropbox is a file hosting service that offers cloud storage, file synchronization, and personal cloud software. Founded in 2007 by Drew Houston and Arash Ferdowsi, Dropbox has over 700 million registered users.