Head of Global Sales Enablement and AI Adoption

Reposted 7 Days Ago
Hiring Remotely in United States
Remote
209K-283K Annually
Senior level
Artificial Intelligence • Cloud • Consumer Web • Productivity • Software • App development • Data Privacy
Dropbox isn’t just a workplace—it’s a living lab for more enlightened ways of working.
The Role
Lead global sales enablement to drive revenue via targeted programs, training, playbooks, onboarding, manager coaching, and analytics. Partner with Sales, RevOps, Product, and Marketing to align enablement to revenue goals and measure impact.
Summary Generated by Built In
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

US Zone 1

This role is not available in Zone 1

US Zone 2
$208,800$282,600 USD
US Zone 3
$185,600$251,200 USD

Skills Required

  • Strong program leadership and change management in a revenue organization (PLG and SLG)
  • Analytical capability to diagnose performance issues using data
  • Ability to influence cross-functionally with or without formal authority
  • Excellent communication and content judgment to simplify and drive adoption
  • Operational rigor: prioritize, enforce governance, and run repeatable processes
  • Familiarity with enablement tools (e.g., Gong, Highspot) and emerging AI technologies
  • Player-coach mindset: build and develop a team while driving outcomes
  • Experience designing global, multi-segment enablement programs (onboarding, playbooks, launch readiness)
  • Experience measuring enablement impact and partnering with RevOps on instrumentation
  • Proven change leadership driving adoption through managers and leadership systems
  • Experience standing up intake, prioritization, governance, and program management discipline
  • Fluency with enterprise and commercial GTM motions, and PLG-to-sales handoffs

What the Team is Saying

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Dropbox Compensation & Benefits Highlights

How does Dropbox ensure its pay and bonus plans are competitive?

Dropbox ensures base pay and bonuses are competitive by benchmarking pay using formal compensation surveys to create salary ranges and bonus targets, and conducting twice-yearly reviews aligned with performance.

Employees describe pay and bonuses as competitive and performance-driven.

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The Company
HQ: San Francisco, CA
2,500 Employees
Year Founded: 2007

What We Do

We're a global community of bold visionaries and resourceful doers who are shaping the future of Dropbox—and with it the future of work. Our Virtual First model combines the flexibility of a distributed workplace with the power of human connection, making space for both meaningful work and meaningful relationships. With our start-up mindset and enterprise-level opportunities, you can be who you are and grow into who you’re meant to be. Here, you can own your impact to make work more intuitive, joyful, and human—for you as a Dropboxer and for hundreds of millions of people worldwide. If you're ready to push boundaries—and yourself—Dropbox is ready for you.

Why Work With Us

We believe people do their best work when empowered with autonomy and harmony, and we understand there’s no substitute for human connection. Our Virtual First model combines the flexibility of remote work with the power of in-person collaboration to create the best of both worlds: a distributed workplace, anchored in community.

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Dropbox Offices

Remote Workspace

Employees work remotely.

While remote work is the primary experience for our employees, we also prioritize opportunities for quarterly in-person collaboration knowing that connection is vital to a thriving workforce. We focus on how we work, not where we work.

Typical time on-site: None
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