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Dropbox

Head of Global Sales Enablement and AI Adoption

Remote - Canada: Select locations · Remote ok
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About this role

Role Description

Dropbox is looking for a strategic leader to build and scale the next generation of Sales Enablement. As Head of Global Sales Enablement & AI Adoption, you will define how our sales organization learns, executes, and performs at scale. You’ll lead the strategy, operating model, and execution for global enablement while leading how sellers and managers adopt AI capabilities to transform the way they work.
 
This role sits at the intersection of Revenue Operations, Sales, Product, Marketing, and AI adoption. You’ll partner closely with executive leadership to identify the highest-impact opportunities to improve seller productivity, accelerate strategic priorities, strengthen manager effectiveness, and create consistent execution across our global go-to-market organization.
 
Success in this role requires balancing strategic thinking with operational excellence. You’ll build scalable enablement programs, modern learning experiences, adoption of AI-enabled workflows and tooling, and measurable operating rhythms that improve business performance—not simply deliver training.
 
If you’re excited about building organizations, influencing executive strategy, and using AI to redefine how revenue teams work, we’d love to meet you.

Responsibilities

  • Define and execute the global Sales Enablement strategy and multi-year roadmap aligned to Dropbox’s go-to-market priorities.
  • Build scalable enablement programs that improve seller productivity, manager effectiveness, onboarding, launch readiness, and revenue performance.
  • Partner with Sales, Revenue Operations, Product, Product Marketing, IT, and executive leadership to drive consistent execution across global teams.
  • Partner with GTM Technology and enterprise AI teams to identify, validate, and drive adoption of AI-enabled workflows that improve seller productivity, while maintaining responsible AI governance and usage.
  • Establish measurement frameworks that connect enablement investments to business outcomes, using data to continuously improve programs and prioritize future investments.
  • Build and develop a high-performing enablement organization and create operating mechanisms that reinforce learning, coaching, and adoption.
  • Foster a culture of continuous improvement by simplifying complex problems, driving change effectively, and ensuring enablement remains tightly connected to customer and business outcomes.
  • Drive adoption, enablement, and change management for AI capabilities introduced into seller and manager workflows.

Requirements

  • Significant experience leading Sales Enablement or Revenue Enablement within a high-growth B2B SaaS organization.
  • Proven success building global enablement strategies that improve seller productivity and measurable business outcomes.
  • Experience partnering with senior executives across Sales, Revenue Operations, Product, Marketing, and Technology to influence strategy and execution.
  • Demonstrated ability to use business performance data to diagnose sales challenges, prioritize investments, and measure program effectiveness.
  • Ability to operate with a transformation-mindset as a builder, willing to break through barriers and challenge the status quo to increase impact.
  • Experience identifying and driving adoption of AI-enabled capabilities within Sales or GTM organizations through enablement, training, and change management.
  • Strong leadership experience building, developing, and coaching high-performing teams through periods of growth and change.
  • Excellent executive communication, influence, and organizational leadership skills.

Preferred Qualifications

  • Experience leading enablement across enterprise, commercial, and product-led sales motions.
  • Experience building AI adoption programs and enablement strategies that accelerate responsible use of AI capabilities with proven results.
  • Deep familiarity with modern sales enablement technologies including CRM, content management, conversation intelligence, learning platforms, and emerging AI solutions.
  • Experience leading globally distributed teams across multiple regions.
  • Demonstrated ability to connect enablement investments to improvements in pipeline creation, conversion, ramp time, productivity, or revenue growth.

Compensation

Company at a glance

Dropbox is the one place to keep life organized and keep work moving. With more than 700 million registered users across 180 countries, we're on a mission to design a more enlightened way of working.

To learn more about working at Dropbox, visit jobs.dropbox.com

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Founded2007
Team Size1,001-5,000 employees
WorkspaceRemote ok
IndustrySoftware Development
Location
Canada
Websitedropbox.com
LinkedInLinkedIn

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