Senior Director, Head of Scaled Sales

About the Role

As a key member of the sales leadership team, the Head of Scaled Sales will report directly to the VP of Sales and will be responsible for leading a team of sales professionals to drive revenue growth and expansion. The ideal candidate will have 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.

The role will be remote, with the selected candidate working from one of the designated locations in the US. This presents an exciting opportunity for a seasoned sales leader to join a dynamic and innovative company, with a strong focus on collaboration, creativity, and customer satisfaction.

What You Will Do

• 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.

What We Are Looking For

• 12+ years of experience in SaaS sales, revenue strategy, growth, or go-to-market leadership.
• Proven track record of success in developing and implementing GTM strategies that drive revenue growth and expansion.
• Strong operator mindset, with the ability to design and implement efficient sales processes and systems.
• Deep fluency in PLG and hybrid GTM models, with a clear understanding of how to balance AI and human judgment to improve outcomes at scale.
• Experience in building and leading high-performing sales teams, with a strong focus on coaching, development, and performance management.
• Strong data-driven decision-making skills, with the ability to analyze complex data sets and develop actionable insights.
• Excellent communication and collaboration skills, with the ability to work effectively with cross-functional teams.
• Strong business acumen, with a deep understanding of the SaaS industry and the competitive landscape.

Nice to Have

• Experience in cloud storage and collaboration, with a strong understanding of the Dropbox product suite.
• Familiarity with sales analytics and data science tools, such as Tableau, Salesforce, and Excel.
• Certification in sales leadership or a related field, such as CSO or CRO.
• Experience in working with remote teams, with a strong ability to manage and motivate teams across different locations.

Benefits and Perks

• Competitive salary and bonus structure, with a strong focus on performance-based rewards.
• Comprehensive benefits package, including health, dental, and vision insurance, as well as a 401(k) matching program.
• Generous PTO policy, with a minimum of 20 days per year, plus holidays and sick leave.
• Remote work stipend, with a budget for home office setup and maintenance.
• Opportunities for professional development and growth, with a strong focus on coaching, mentoring, and training.
• Access to the latest technology and tools, with a budget for ongoing education and innovation.
• Collaborative and dynamic work environment, with a strong focus on teamwork, creativity, and customer satisfaction.

• Develop a strong understanding of the SaaS industry and the competitive landscape, with a focus on cloud storage and collaboration.
• Showcase your experience in developing and implementing successful GTM strategies, with a focus on data-driven decision-making and sales process optimization.
• Highlight your ability to lead cross-functional teams and drive business outcomes, with a strong focus on coaching, development, and performance management.
• Be prepared to discuss your experience in balancing AI and human judgment to improve outcomes at scale, with a focus on the role of AI in sales and customer engagement.
• Emphasize your strong communication and collaboration skills, with the ability to work effectively with cross-functional teams and drive business outcomes.
• Research the company culture and values, with a focus on collaboration, creativity, and customer satisfaction.
• Prepare examples of your experience in working with remote teams, with a strong ability to manage and motivate teams across different locations.