Director, Head of Scaled Sales

Dropbox is a Virtual First company. For this role, we are currently only authorized to hire candidates from the following provinces: Alberta, British Columbia, Ontario, and Saskatchewan.

Role Description

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.

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.

Compensation

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).

Read more about our benefits here.

Company Description

Dropbox isn't just a workplace\u2014it's a living lab for designing a more enlightened way of working. We're a global community of bold visionaries and resourceful doers shaping the future of Dropbox and, in turn, the future of work. Our Virtual First model combines the autonomy of a distributed workplace with the power of human connection, creating space for meaningful work and lasting relationships. With a startup mindset and enterprise-level opportunities, we expect Dropbox employees to think critically, stay curious, and use modern tools, including AI, to improve how work gets done. Here, you can be who you are and grow into who you're meant to be. You own your impact, helping make work more intuitive, joyful, and human for yourself and hundreds of millions of people worldwide. If you're ready to push boundaries and challenge yourself, Dropbox is ready for you.

Team Description

The Dropbox Sales and Channel Team brings the power of enlightened work to organizations worldwide. We deliver solutions that transform how companies collaborate. We don't just sell products\u2014we create partnerships that help companies leverage Dropbox Business to ignite new ways of working. From crafting sales strategies to analyzing business performance, we work with our customers, channel partners, and business decision makers to develop insights, identify opportunities, and do the planning and execution necessary to drive growth. If you're excited about creating partnerships inside the organization and out, join the Sales team.

Virtual First

Dropbox's Virtual First way of working is designed to help people do their best work with flexibility, autonomy, and connection. Day to day, teams work remotely with nonlinear schedules and core collaboration hours that support deep focus and individual working styles. We prioritize asynchronous communication to improve clarity, respect deep work time, and reduce unnecessary meetings. While remote work is the primary experience for our employees, we also prioritize intentional, in-person connection. We bring teams together through regular team gatherings, on-demand workspaces, and Dropbox Neighborhood events in order to strengthen team cohesion, foster creativity, and enhance momentum. Virtual First is built to provide the same access to opportunity, growth, and impact for everyone, regardless of location.

This role requires travel to offsites and various other team gatherings (approximately 5-10% of the year or 2-3 days per quarter). We provide advance notice when possible and encourage candidates to discuss any accommodation needs during the interview process.

AI Fluency

AI fluency is a core part of how we work and grow. It's not about being an expert\u2014it's about using these tools thoughtfully and effectively to improve your work and support others.

We look for four key behaviors in candidates:

• Ownership: You use AI responsibly by protecting data, applying sound judgment, and taking accountability for the quality and accuracy of your work.
• Experimentation: You explore new AI capabilities and apply them to improve workflows within approved tools and practices.
• Leverage: You use AI to enhance thinking, improve efficiency, and increase your impact and your team's.
• Learning: You stay current on emerging AI tools and trends, continuously build your skills, and share what you learn with others.

Together, these behaviors help build a workforce where technology amplifies human judgment, creativity, and impact.

Dropbox supports responsible use of AI for preparation, but misrepresentation of skills or experience is not permitted. See our AI Principles.

Dropbox is an equal opportunity employer. We are a welcoming place for everyone, and we do our best to make sure all people feel supported and connected at work.