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 The Director of Sales Enablement will drive revenue growth by designing and running targeted enablement programs that measurably improve seller performance. This role uses data and field insights to identify performance gaps, optimize sales motions, and deliver training, content, and programs that help sellers execute against business priorities. The Director leads a cross-functional enablement team and partners closely with Sales, RevOps, Product, and Marketing to ensure programs are tightly aligned to revenue targets and deliver provable impact.

They will report directly to the Head of Revenue Operations. Enablement is the bridge between strategy and seller execution and ensures: The field knows what to do, when to do it, and how to do it well

Sales priorities translate into consistent behaviors across segments/regions

Leaders have visibility into what’s working, what’s not, and what to change Responsibilities Core Responsibilities Program Leadership: Design and deliver global enablement programs that drive measurable revenue impact, tailored to regional and cultural nuances

Insights & Analytics: Leverage performance data to diagnose gaps, identify root causes, and prioritize high-impact interventions

Training & Content Strategy: Develop role-based training and assets aligned to field needs and business priorities

Cross-Functional Alignment: Partner with Sales, RevOps, and executive leadership to align enablement with revenue goals and strategic initiatives

Impact & Optimization: Track adoption and outcomes; continuously refine strategy, messaging, and delivery to maximize effectiveness Core Programs New Hire Ramp: Structured onboarding, time-to-productivity plans, certification, and manager reinforcement

Sales Process & ROEs: Define, document, and scale sales processes and rules of engagement in partnership with Sales and RevOps

Field Enablement (Multi-Role): Deliver role-specific onboarding, plays, and reinforcement across Sales, Channel, Solutions, and Customer Success—aligned to a unified GTM motion

Playbooks: Translate priority motions (new logo, expansion, vertical, competitive) into clear, actionable playbooks with defined stages, exit criteria, roles, tooling signals, and required assets

Launch Readiness: Drive field readiness for product, pricing, and packaging updates (talk tracks, discovery guides, objection handling, FAQs)

Skills & Methodology: Embed consistent selling disciplines (discovery, value selling, SPICED or equivalent, negotiation, mutual action plans, forecasting)

AI and Agent assist: ID where to best leverage AI to scale enablement programs and increase time to information and reduce time out of the field.

Manager Enablement: Equip frontline leaders with coaching frameworks, scorecards, and inspection rhythms

Reinforcement & Communications: Sustain behavior change through recurring learning, office hours, certification refreshers, and structured field communications Requirements Strong program leadership and change management in a revenue org in both PLG and SLG environments

Analytical and comfortable diagnosing performance issues with data

Ability to influence with or without authority

Excellent communication and content judgment; knows how to simplify and drive adoption

Operational rigor — can prioritize, say no, and run repeatable processes

Familiarity with enablement based tools (e.g., Gong, Highspot) and emerging AI tech

Player-coach mindset: develops a team while still driving outcomes Preferred Qualifications Scaled enablement leadership: Led enablement for a multi-segment and/or global sales org; comfortable designing programs that work across regions.

Strong operating muscle: Experience standing up intake/prioritization, governance, and program management discipline (not just training).

GTM motion fluency: Familiar with enterprise + commercial motions (and PLG-to-sales assisted handoffs if relevant).

Measurement credibility: Demonstrated ability to tie enablement to measurable outcomes and influence RevOps instrumentation.

Change leadership: Track record driving adoption through managers and leadership systems, not just content delivery.

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).

Company Description Read more about our benefits here. 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.