Head of Global Sales Enablement and AI Adoption

About the role

Dropbox is seeking a Head of Global Sales Enablement and AI Adoption to lead the strategy and execution of sales enablement programs across all regions worldwide. This role sits at the intersection of go-to-market operations and artificial intelligence integration, driving how sales teams adopt and AI tools in their daily workflows and customer interactions. The position reports to senior leadership and works closely with cross-functional teams including sales, product, marketing, and engineering on a global scale. The successful candidate will shape the vision for how Dropbox's global sales organization learns, adapts, and scales with emerging AI capabilities while maintaining a focus on revenue growth and customer satisfaction.

Key facts

What you'll do

• Define and own the global sales enablement strategy aligned with Dropbox's business objectives and long-term growth targets across every region.
• Design and deliver AI adoption programs that help sales teams integrate machine learning tools into their daily selling processes and workflows.
• Partner with product and engineering teams to gather feedback on AI features and translate them into practical enablement content for reps.
• Build a centralized knowledge base of sales playbooks, battle cards, and AI-driven selling guides that are accessible to all regions and teams.
• Oversee the creation and delivery of training curricula focused on AI tools, data-driven selling techniques, and deep customer insights for sales staff.
• Measure the impact of enablement programs through key performance indicators and iterate on approaches based on quantitative data and qualitative feedback.
• Collaborate with marketing to ensure sales messaging consistently reflects the value of Dropbox's AI-powered features and overall product capabilities in the market.
• Coach and develop a team of enablement specialists who execute programs across different geographies, sales cycles, and organizational structures effectively.
• Lead cross-functional initiatives that align sales workflows with Dropbox's AI product roadmap, release cadence, and go-to-market priorities throughout the year.
• Represent the sales enablement function in executive forums, contributing to strategic decisions about AI investment, adoption roadmaps, and resource allocation.
• Establish best practices for AI-assisted selling and ensure they are documented, shared, and continuously refined based on results from field teams.

Requirements

• Proven track record leading sales enablement or a related function within a global technology organization with multiple regional teams and markets.
• Deep understanding of artificial intelligence and machine learning concepts as they apply to sales processes, customer engagement, and revenue operations.
• Experience building and managing enablement teams across multiple regions or time zones with a focus on consistency and quality delivery.
• Strong communication skills with the ability to present complex AI concepts to diverse audiences including executives, managers, and frontline sales representatives.
• Demonstrated success designing and scaling enablement programs that measurably improved sales performance, team productivity, and overall adoption rates across organizations.
• Bachelor's degree or equivalent practical experience in business, marketing, or a related field from an accredited institution or program.
• At least 10 years of professional experience in sales enablement, sales operations, or a closely related discipline within a technology company.
• Experience working with AI or data analytics platforms to inform sales strategy, coaching decisions, and performance improvement initiatives over time.
• Familiarity with change management methodologies and the ability to drive organizational adoption of new processes, tools, and technologies across large teams.

Nice to have

• Familiarity with Dropbox's product suite including cloud storage, collaboration tools, and AI-powered features that support modern sales workflows.
• Background in enterprise software or SaaS sales environments with complex, multi-stakeholder buying processes and long sales cycles.
• Experience implementing change management practices to drive organizational adoption of new technologies and working methods across distributed teams.
• Knowledge of sales methodologies such as MEDDIC, Challenger, or SPIN and how they integrate with AI-driven insights and automation tools.

Skills & tools

• Proficiency in sales enablement platforms and learning management systems for content delivery, tracking, and reporting on learner engagement.
• Experience with AI and machine learning frameworks, including natural language processing, predictive analytics, and recommendation engines used in sales contexts.
• Strong data analysis skills using tools such as spreadsheets, dashboards, or business intelligence software to inform enablement strategy and decisions.
• Familiarity with CRM systems and sales engagement platforms commonly used in enterprise environments for pipeline management and forecasting.
• Excellent project management abilities with the capacity to juggle multiple initiatives across global teams while maintaining clear priorities and deadlines.
• Comfort with emerging AI technologies and a genuine willingness to continuously learn and adapt to new tools and methodologies.

Practical notes

• This role is fully remote and based in Canada, with the expectation of working within select Canadian locations as designated by the company.
• Candidates should be prepared to coordinate with teams across multiple time zones and maintain flexible working hours to support global operations.
• The hiring process may include multiple interview rounds with stakeholders from sales, product, and engineering departments at Dropbox.
• Dropbox values diversity and encourages applicants from all backgrounds to apply for this position and contribute to the company's mission.
• This is a full-time position with a focus on strategic leadership and hands-on program execution in the sales enablement space.

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.