Senior Director, Head of Scaled Sales

About the Role

As the leader of this sales motion, the Senior Director will design and implement segmentation, coverage, and experimentation systems to determine when, where, and how sales engages self-serve customers. This will involve close collaboration with marketing, data science, and sales analytics teams to turn signals into action and drive business outcomes.

The Senior Director will report to the VP of Sales and will be responsible for building and leading a high-performing team of sales professionals.

What You Will Do

• Build a self-serve segmentation model to identify 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.

What We Are Looking For

• 12+ years of experience in SaaS sales, revenue strategy, growth, or go-to-market leadership.
• Proven track record of driving growth and conversion in a sales-assisted PLG motion.
• Deep fluency in PLG and hybrid GTM models, with a strong understanding of sales analytics and data-driven decision making.
• Experience building and leading high-performing sales teams, with a strong operator mindset and ability to drive results.
• Strong collaboration and communication skills, with the ability to partner closely with cross-functional teams.
• Bachelor's degree in a relevant field, such as business, marketing, or computer science.

Nice to Have

• Experience with AI and machine learning, with a clear point of view on how to balance AI and human judgment to improve outcomes at scale.
• Familiarity with sales automation tools and technologies, such as Salesforce or HubSpot.
• Experience working in a fast-paced, rapidly changing environment, with a strong ability to adapt and innovate.

Benefits and Perks

• Competitive salary and equity package.
• Comprehensive benefits package, including health, dental, and vision insurance.
• Generous PTO and sick leave policies.
• Remote work stipend and support for home office setup.
• Opportunities for professional growth and development, including training and education programs.
• Access to a dynamic and supportive community of professionals, with regular team-building events and activities.

• Research Dropbox's product-led growth model and be prepared to discuss how you would drive conversion and expansion in a sales-assisted motion.
• Develop a strong understanding of GTM strategies and sales analytics, and be prepared to provide examples of how you have used data to inform sales decisions.
• Showcase your ability to build and lead high-performing sales teams, and highlight any experience you have with sales automation tools and technologies.
• Be prepared to discuss how you balance AI and human judgment in sales decision making, and provide examples of how you have used AI to drive business outcomes.
• Practice your ability to communicate complex sales concepts and strategies to both technical and non-technical audiences, and be prepared to provide examples of how you have partnered with cross-functional teams to drive business outcomes.
• Research the company culture and values, and be prepared to discuss how you would contribute to and thrive in a dynamic and supportive community of professionals.
• Prepare any questions you may have about the role, the company, or the future of the sales-assisted PLG motion, and be ready to ask them during the interview process.