Head of Global Sales Enablement and AI Adoption

Remote - Canada: Select locations·remote·Customer Intelligence, Strategy & Enablement (Sub Team)·sales·Posted August 13, 2026
Apply on Dropbox →

<div> <div> <h2 class=&quot;p1&quot;><span class=&quot;s1&quot;>Role Description</span></h2> <div> <div> <div><span class=&quot; author-d-4z65zz66zl57z75zyiz66zfr2fz87zwz89znujgz72zurz70zuz72z610z65zz65zlez84zz89zz72z9lz84z1z87zz86zz86ziidbe&quot;>Dropbox is looking for a strategic leader to build and scale the next generation of Sales Enablement. As Head of Global Sales Enablement &amp; AI </span><span class=&quot; author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qowz81zz86zcvlz122zs3wgz73zz76zz70zhbz122zz78zloz87zz67zjh3xz86z8j4dz70z&quot;>Adoption</span><span class=&quot; author-d-4z65zz66zl57z75zyiz66zfr2fz87zwz89znujgz72zurz70zuz72z610z65zz65zlez84zz89zz72z9lz84z1z87zz86zz86ziidbe&quot;>, 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 </span>while leading how sellers and managers adopt AI capabilities to <span class=&quot; author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qowz81zz86zcvlz122zs3wgz73zz76zz70zhbz122zz78zloz87zz67zjh3xz86z8j4dz70z&quot;>transform the way they work.</span></div> <div>&nbsp;</div> <div><span class=&quot; author-d-4z65zz66zl57z75zyiz66zfr2fz87zwz89znujgz72zurz70zuz72z610z65zz65zlez84zz89zz72z9lz84z1z87zz86zz86ziidbe&quot;>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 </span><span class=&quot; author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qowz81zz86zcvlz122zs3wgz73zz76zz70zhbz122zz78zloz87zz67zjh3xz86z8j4dz70z&quot;>priorities</span><span class=&quot; author-d-4z65zz66zl57z75zyiz66zfr2fz87zwz89znujgz72zurz70zuz72z610z65zz65zlez84zz89zz72z9lz84z1z87zz86zz86ziidbe&quot;>, strengthen manager effectiveness, and create consistent execution across our global go-to-market organization.</span></div> <div>&nbsp;</div> <div><span class=&quot; author-d-4z65zz66zl57z75zyiz66zfr2fz87zwz89znujgz72zurz70zuz72z610z65zz65zlez84zz89zz72z9lz84z1z87zz86zz86ziidbe&quot;>Success in this role requires balancing strategic thinking with operational excellence. You’ll build scalable enablement programs, modern learning experiences, </span>adoption of AI-enabled workflows and <span class=&quot; author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qowz81zz86zcvlz122zs3wgz73zz76zz70zhbz122zz78zloz87zz67zjh3xz86z8j4dz70z&quot;>tooling</span><span class=&quot; author-d-4z65zz66zl57z75zyiz66zfr2fz87zwz89znujgz72zurz70zuz72z610z65zz65zlez84zz89zz72z9lz84z1z87zz86zz86ziidbe&quot;>, and measurable operating rhythms that improve business performance—not simply deliver training.</span></div> <div>&nbsp;</div> <div><span class=&quot; author-d-4z65zz66zl57z75zyiz66zfr2fz87zwz89znujgz72zurz70zuz72z610z65zz65zlez84zz89zz72z9lz84z1z87zz86zz86ziidbe&quot;>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.</span></div> </div> </div> <h2 class=&quot;p1&quot;><span class=&quot;s1&quot;>Responsibilities</span></h2> <div> <ul class=&quot;listtype-bullet listindent1 list-bullet1&quot; data-testid=&quot;bullet-list&quot; data-test-indentation=&quot;1&quot;> <li><span class=&quot; author-d-4z65zz66zl57z75zyiz66zfr2fz87zwz89znujgz72zurz70zuz72z610z65zz65zlez84zz89zz72z9lz84z1z87zz86zz86ziidbe&quot;>Define and execute the global Sales Enablement strategy and multi-year roadmap aligned to Dropbox’s go-to-market priorities.</span></li> <li><span class=&quot; author-d-4z65zz66zl57z75zyiz66zfr2fz87zwz89znujgz72zurz70zuz72z610z65zz65zlez84zz89zz72z9lz84z1z87zz86zz86ziidbe&quot;>Build scalable enablement programs that improve seller productivity, manager effectiveness, onboarding, launch readiness, and revenue performance.</span></li> <li><span class=&quot; author-d-4z65zz66zl57z75zyiz66zfr2fz87zwz89znujgz72zurz70zuz72z610z65zz65zlez84zz89zz72z9lz84z1z87zz86zz86ziidbe&quot;>Partner with Sales, Revenue Operations, Product, Product Marketing, IT, and executive leadership to drive consistent execution across global teams.</span></li> <li>Partner with GTM Technology and enterprise AI teams to identify, validate, and drive adoption of AI-enabled workflows that improve seller productivity<span class=&quot; author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qowz81zz86zcvlz122zs3wgz73zz76zz70zhbz122zz78zloz87zz67zjh3xz86z8j4dz70z&quot;>, while maintaining responsible AI governance and usage.</span></li> <li><span class=&quot; author-d-4z65zz66zl57z75zyiz66zfr2fz87zwz89znujgz72zurz70zuz72z610z65zz65zlez84zz89zz72z9lz84z1z87zz86zz86ziidbe&quot;>Establish measurement frameworks that connect enablement investments to business outcomes, using data to continuously improve programs and prioritize future investments.</span></li> <li><span class=&quot; author-d-4z65zz66zl57z75zyiz66zfr2fz87zwz89znujgz72zurz70zuz72z610z65zz65zlez84zz89zz72z9lz84z1z87zz86zz86ziidbe&quot;>Build and develop a high-performing enablement organization and create operating mechanisms that reinforce learning, coaching, and adoption.</span></li> <li><span class=&quot; author-d-4z65zz66zl57z75zyiz66zfr2fz87zwz89znujgz72zurz70zuz72z610z65zz65zlez84zz89zz72z9lz84z1z87zz86zz86ziidbe&quot;>Foster a culture of continuous improvement by simplifying complex problems, driving change effectively, and ensuring enablement remains tightly connected to customer and business outcomes.</span></li> <li><span class=&quot; author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qoxwovoz80zfz73zz75zz76zbexz75zhz122zz71zyolz72zbfz82zz76z87z90zez72zuz65z&quot;>Drive adoption, enablement, and change management for AI capabilities introduced into seller and manager workflows</span><span class=&quot; author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qowz81zz86zcvlz122zs3wgz73zz76zz70zhbz122zz78zloz87zz67zjh3xz86z8j4dz70z&quot;>.</span></li> </ul> </div> <h2 class=&quot;p1&quot;><span class=&quot;s1&quot;>Requirements</span></h2> <div> <ul class=&quot;listtype-bullet listindent1 list-bullet1&quot; data-testid=&quot;bullet-list&quot; data-test-indentation=&quot;1&quot;> <li><span class=&quot; author-d-4z65zz66zl57z75zyiz66zfr2fz87zwz89znujgz72zurz70zuz72z610z65zz65zlez84zz89zz72z9lz84z1z87zz86zz86ziidbe&quot;>Significant experience leading Sales Enablement or Revenue Enablement within a high-growth B2B SaaS organization.</span></li> <li><span class=&quot; author-d-4z65zz66zl57z75zyiz66zfr2fz87zwz89znujgz72zurz70zuz72z610z65zz65zlez84zz89zz72z9lz84z1z87zz86zz86ziidbe&quot;>Proven success building global enablement strategies that improve seller productivity and measurable business outcomes.</span></li> <li><span class=&quot; author-d-4z65zz66zl57z75zyiz66zfr2fz87zwz89znujgz72zurz70zuz72z610z65zz65zlez84zz89zz72z9lz84z1z87zz86zz86ziidbe&quot;>Experience partnering with senior executives across Sales, Revenue Operations, Product, Marketing, and Technology to influence strategy and execution.</span></li> <li><span class=&quot; author-d-4z65zz66zl57z75zyiz66zfr2fz87zwz89znujgz72zurz70zuz72z610z65zz65zlez84zz89zz72z9lz84z1z87zz86zz86ziidbe&quot;>Demonstrated ability to use business performance data to diagnose sales challenges, prioritize investments, and measure program effectiveness.</span></li> <li><span class=&quot; author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qowz81zz86zcvlz122zs3wgz73zz76zz70zhbz122zz78zloz87zz67zjh3xz86z8j4dz70z&quot;>Ability to operate with a transformation-mindset as a builder, willing to break through barriers and challenge the status quo to increase impact.</span></li> <li>Experience <span class=&quot; author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qowz81zz86zcvlz122zs3wgz73zz76zz70zhbz122zz78zloz87zz67zjh3xz86z8j4dz70z&quot;>identifying and </span>driving adoption of AI-enabled capabilities within Sales or GTM organizations through enablement, training, and change management.</li> <li><span class=&quot; author-d-4z65zz66zl57z75zyiz66zfr2fz87zwz89znujgz72zurz70zuz72z610z65zz65zlez84zz89zz72z9lz84z1z87zz86zz86ziidbe&quot;>Strong leadership experience building, developing, and coaching high-performing teams through periods of growth and change.</span></li> <li><span class=&quot; author-d-4z65zz66zl57z75zyiz66zfr2fz87zwz89znujgz72zurz70zuz72z610z65zz65zlez84zz89zz72z9lz84z1z87zz86zz86ziidbe&quot;>Excellent executive communication, influence, and organizational leadership skills.</span></li> </ul> </div> <h2>Preferred Qualifications</h2> <ul class=&quot;listtype-bullet listindent1 list-bullet1&quot; data-testid=&quot;bullet-list&quot; data-test-indentation=&quot;1&quot;> <li><span class=&quot; author-d-4z65zz66zl57z75zyiz66zfr2fz87zwz89znujgz72zurz70zuz72z610z65zz65zlez84zz89zz72z9lz84z1z87zz86zz86ziidbe&quot;>Experience leading enablement across enterprise, commercial, and product-led sales motions.</span></li> <li>Experience building AI adoption programs and enablement strategies that accelerate responsible use of AI capabilities<span class=&quot; author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qowz81zz86zcvlz122zs3wgz73zz76zz70zhbz122zz78zloz87zz67zjh3xz86z8j4dz70z&quot;> with proven results.</span></li> <li><span class=&quot; author-d-4z65zz66zl57z75zyiz66zfr2fz87zwz89znujgz72zurz70zuz72z610z65zz65zlez84zz89zz72z9lz84z1z87zz86zz86ziidbe&quot;>Deep familiarity with modern sales enablement technologies including CRM, content management, conversation intelligence, learning platforms, and emerging AI solutions.</span></li> <li><span class=&quot; author-d-4z65zz66zl57z75zyiz66zfr2fz87zwz89znujgz72zurz70zuz72z610z65zz65zlez84zz89zz72z9lz84z1z87zz86zz86ziidbe&quot;>Experience leading globally distributed teams across multiple regions.</span></li> <li><span class=&quot; author-d-4z65zz66zl57z75zyiz66zfr2fz87zwz89znujgz72zurz70zuz72z610z65zz65zlez84zz89zz72z9lz84z1z87zz86zz86ziidbe&quot;>Demonstrated ability to connect enablement investments to improvements in pipeline creation, conversion, ramp time, productivity, or revenue growth.</span></li> </ul> <h2 data-usually-unique-id=&quot;044234883370604133046166&quot;><span class=&quot; author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qowz81zqz90zkz74zz76zeez80zz68zz89zz88zvqz86zuxlz73zexxz80zz73z6d6z72zz79zsz77z&quot;>Compensation</span></h2> </div> </div>

More open roles at Dropbox