Director, Global Sales Enablement

Posted Yesterday
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Hiring Remotely in Canada
Remote
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 programs that drive measurable revenue by diagnosing performance gaps, creating role-based training and playbooks, aligning cross-functionally, and optimizing adoption through analytics and manager-led reinforcement.
Summary Generated by Built In
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

Skills Required

  • Program leadership and change management in revenue organizations (PLG and SLG)
  • Analytical ability to diagnose performance issues with data
  • Ability to influence with or without 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: develop a team while driving outcomes
  • Led enablement for multi-segment and/or global sales organizations
  • Experience establishing intake/prioritization, governance, and program management discipline
  • Fluency with enterprise and commercial GTM motions, including PLG-to-sales handoffs
  • Proven ability to tie enablement to measurable outcomes and influence RevOps instrumentation
  • Track record driving adoption through managers and leadership systems

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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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.

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