About the role
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
Not the right fit? Search for Director, Global Sales Enablement jobs in Canada
About Dropbox
Dropbox is the one place to keep life organized and keep work moving. With more than 700 million registered users across 180 countries, we're on a mission to design a more enlightened way of working. Dropbox is headquartered in San Francisco, CA, and has offices around the world.
To learn more about working at Dropbox, visit dropbox.com/jobs
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About the role
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
Not the right fit? Search for Director, Global Sales Enablement jobs in Canada
About Dropbox
Dropbox is the one place to keep life organized and keep work moving. With more than 700 million registered users across 180 countries, we're on a mission to design a more enlightened way of working. Dropbox is headquartered in San Francisco, CA, and has offices around the world.
To learn more about working at Dropbox, visit dropbox.com/jobs
We also have a few simple guidelines to keep this space respectful and productive. Please avoid:
- Harassing other people or using language that’s hateful, offensive, vulgar, or advocates violence
- Trolling, fraud and spamming
- Violating someone else’s rights or privacy
- Advertising or soliciting donations
- Link baiting
- Posting off topic comments or thread hijacking
We may remove comments that violate these guidelines.