Head of Global Sales Enablement and AI Adoption

Namely; Saskatchewan; Remote; CAD 120,000 - 190,000; Full time

Job summary

Dropbox is seeking a strategic Head of Global Sales Enablement & AI Adoption to shape how our sales teams learn, perform, and scale with AI-enabled workflows. You will lead the strategy, operating model, and execution for global enablement while partnering with executive leadership to drive high-impact outcomes across a dynamic GTM organization.

This role sits at the intersection of Revenue Ops, Sales, Product, Marketing, and AI adoption, requiring a blend of strategic thinking and operational

Qualifications

• 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 business outcomes.
• Experience partnering with senior executives across Sales, Revenue Operations, Product, Marketing, and Technology.
• Ability to diagnose sales challenges using business performance data and measure program impact.

Responsibilities

• Define and execute global Sales Enablement strategy and multi-year roadmap aligned to GTM priorities.
• Build scalable enablement programs to improve seller productivity and revenue performance.
• Partner with Sales, Revenue Ops, Product, IT, and leadership to ensure consistent execution across teams.
• Drive adoption of AI-enabled workflows while ensuring responsible AI governance.
• Establish measurement frameworks linking enablement investments to business outcomes.

Skills

Sales Enablement

Revenue Enablement

High-growth SaaS

Executive collaboration

Leadership

Tools

CRM

Content Management

Conversation Intelligence

Learning Platforms

AI Solutions

Job description

Dropbox is a Virtual First company. For this role, we are currently only authorized to hire candidates from the following provinces: Alberta, British Columbia, Ontario, and Saskatchewan.

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

The range listed above is the expected annual salary/OTE (On-Target Earnings) for this role, subject to change.

Salary/OTE is just one component of Dropbox’s total rewards package. All regular employees are also eligible for the corporate bonus program or a sales incentive (target included in OTE) as well as stock in the form of Restricted Stock Units (RSUs).

Read more about our benefits here.

Company Description

Dropbox isn’t just a workplace—it’s a living lab for designing a more enlightened way of working. We’re a global community of bold visionaries and resourceful doers shaping the future of Dropbox and, in turn, the future of work. Our Virtual First model combines the autonomy of a distributed workplace with the power of human connection, creating space for meaningful work and lasting relationships. With a startup mindset and enterprise-level opportunities, we expect Dropbox employees to think critically, stay curious, and use modern tools, including AI, to improve how work gets done. Here, you can be who you are and grow into who you’re meant to be. You own your impact, helping make work more intuitive, joyful, and human for yourself and hundreds of millions of people worldwide. If you’re ready to push boundaries and challenge yourself, Dropbox is ready for you.

Team Description

The Dropbox Sales and Channel Team brings the power of enlightened work to organizations worldwide. We deliver solutions that transform how companies collaborate. We don’t just sell products—we create partnerships that help companies leverage Dropbox Business to ignite new ways of working. From crafting sales strategies to analyzing business performance, we work with our customers, channel partners, and business decision makers to develop insights, identify opportunities, and do the planning and execution necessary to drive growth. If you're excited about creating partnerships inside the organization and out, join the Sales team.

Virtual First

Dropbox’s Virtual First way of working is designed to help people do their best work with flexibility, autonomy, and connection. Day to day, teams work remotely with nonlinear schedules and core collaboration hours that support deep focus and individual working styles. We prioritize asynchronous communication to improve clarity, respect deep work time, and reduce unnecessary meetings. While remote work is the primary experience for our employees, we also prioritize intentional, in-person connection. We bring teams together through regular team gatherings, on-demand workspaces, and Dropbox Neighborhood events in order to strengthen team cohesion, foster creativity, and enhance momentum. Virtual First is built to provide the same access to opportunity, growth, and impact for everyone, regardless of location.

This role requires travel to offsites and various other team gatherings (approximately 5-10% of the year or 2-3 days per quarter). We provide advance notice when possible and encourage candidates to discuss any accommodation needs during the interview process.

AI Fluency

AI fluency is a core part of how we work and grow. It’s not about being an expert—it’s about using these tools thoughtfully and effectively to improve your work and support others.

We look for four key behaviors in candidates:

• Ownership: You use AI responsibly by protecting data, applying sound judgment, and taking accountability for the quality and accuracy of your work.
• Experimentation: You explore new AI capabilities and apply them to improve workflows within approved tools and practices.
• Leverage: You use AI to enhance thinking, improve efficiency, and increase your impact and your team’s.
• Learning: You stay current on emerging AI tools and trends, continuously build your skills, and share what you learn with others.

Together, these behaviors help build a workforce where technology amplifies human judgment, creativity, and impact.

Dropbox supports responsible use of AI for preparation, but misrepresentation of skills or experience is not permitted. To learn more, see our approach to AI in hiring.

Dropbox is an equal opportunity employer. We are a welcoming place for everyone, and we do our best to make sure all people feel supported and connected at work.

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