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.
Role Description ResponsibilitiesRequirementsPreferred Qualifications
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.
- 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.
- 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.
- 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.
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
Dropbox Chicago, Illinois, USA Office
Chicago, IL, United States
Similar Jobs at Dropbox
Artificial Intelligence • Cloud • Consumer Web • Productivity • Software • App development • Data Privacy
Own and grow strategic distribution and ecosystem partnerships across AI, hardware, developer, and SaaS ecosystems. Identify opportunities, build business cases and financial models, lead commercial negotiations, manage partnership lifecycle, and collaborate cross-functionally to drive customer acquisition, product adoption, and revenue growth while using data and AI-enabled tools to optimize outcomes.
Top Skills:
AIAi AgentsAutomationCloud ServicesDeveloper PlatformsHardware EcosystemsSaaS
Artificial Intelligence • Cloud • Consumer Web • Productivity • Software • App development • Data Privacy
Lead global field and partner marketing to drive Sales-Led Growth (SLG) and partner-sourced pipeline. Own regional GTM strategy, ABM, mid-to-bottom funnel demand, partner co-marketing with AI ecosystems, PLG-to-SLG monetization, sales alignment, events, and scaling a multi-disciplinary global marketing team tied to pipeline outcomes.
Top Skills:
AbmChatgptClaudeCloud MarketplacesCRMGeminiIntent Data PlatformsMapPrm
Artificial Intelligence • Cloud • Consumer Web • Productivity • Software • App development • Data Privacy
Lead design vision and execution for Dropbox's multi-product ecosystem, crafting high-trust AI-powered experiences that activate customer content. Drive strategy through execution, mentor designers, partner with cross-functional teams, and raise design quality across interaction, systems, prototyping, and implementation to deliver elegant, trustworthy product experiences.
What you need to know about the Chicago Tech Scene
With vibrant neighborhoods, great food and more affordable housing than either coast, Chicago might be the most liveable major tech hub. It is the birthplace of modern commodities and futures trading, a national hub for logistics and commerce, and home to the American Medical Association and the American Bar Association. This diverse blend of industry influences has helped Chicago emerge as a major player in verticals like fintech, biotechnology, legal tech, e-commerce and logistics technology. It’s also a major hiring center for tech companies on both coasts.
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
- Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
- Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
- Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory
