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Senior Director, Revenue Operations

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Remote - Canada: Select locations
GCO Office (Sub Team)
This position may no longer be active.View all open positions at Dropbox

About the Role

At Dropbox, a Most Loved Workplace® certified employer in the Software space, Design a more enlightened way of working for everyone, everywhere.

<h2 class="p1"><span class="s1">Role Description</span></h2>

<div><span class=" author-d-4z65zz66zl57z75zyiz66zfr2fz87zwz89znujgz72zurz70zuz72z610z65zz65zlez84zz89zz72z9lz84z1z87zz86zz86ziidbe">Dropbox is seeking a Head of Revenue Operations to lead and scale the operational foundation of Dropbox's global B2B go-to-market organization. This role will be responsible for driving operational excellence across the revenue engine, enabling predictable, efficient growth across </span><span class="thread-833045333357425429963299 author-d-4z65zz66zl57z75zyiz66zfr2fz87zwz89znujgz72zurz70zuz72z610z65zz65zlez84zz89zz72z9lz84z1z87zz86zz86ziidbe">SMB, Mid-Market, and Enterprise segments.</span> <span class=" author-d-4z65zz66zl57z75zyiz66zfr2fz87zwz89znujgz72zurz70zuz72z610z65zz65zlez84zz89zz72z9lz84z1z87zz86zz86ziidbe">This role will also oversee Marketing Operations, ensuring alignment between demand generation, pipeline creation, and revenue outcomes across the full customer lifecycle.</span></div>

<div> </div>

<div><span class=" author-d-4z65zz66zl57z75zyiz66zfr2fz87zwz89znujgz72zurz70zuz72z610z65zz65zlez84zz89zz72z9lz84z1z87zz86zz86ziidbe">This leader will own revenue planning, forecasting, revenue operations, incentives, systems, analytics, and GTM infrastructure. Partnering closely with Sales, Finance, Product, Marketing, and Customer leadership, this role will play a critical role in strengthening execution rigor, improving forecast accuracy, and enabling Dropbox to scale across products, regions, and sales motions, including product-led, sales-assisted, and enterprise.</span></div>

<h2 class="p1"><span class="s1">Responsibilities</span></h2>

<ul>

<li>

<div>Own and continuously improve Dropbox's end-to-end revenue operating model, including segmentation, account coverage, territory design, role clarity, and cross-functional handoffs across Sales, Marketing, Customer Success, and Support</div>

</li>

<li>

<div>Lead annual and quarterly revenue planning processes, including bookings targets, quota setting, capacity planning, territory design, and ramp assumptions</div>

</li>

<li>

<div>Establish forecasting rigor, pipeline management processes, inspection cadences, and performance management standards that improve visibility and predictability across the business</div>

</li>

<li>

<div>Define, track, and operationalize core revenue and GTM KPIs (e.g., pipeline coverage, win rates, ACV, sales cycle, productivity, CAC, velocity, retention, and expansion), identifying performance gaps and driving operational improvements</div>

</li>

<li>

<div>Lead revenue operations across the customer lifecycle, from lead routing and opportunity management through renewal and expansion, ensuring scalable processes, governance, and execution excellence</div>

</li>

<li>

<div>Partner with Data Science on analytical support and insights, experimentation and cadence for biz performance updates</div>

</li>

<li>

<div>Partner with Finance on revenue planning, pricing operations, discounting frameworks, deal governance, sales compensation, and incentive design to support growth and operational discipline</div>

</li>

<li>

<div>Partner with Customer Success and Support leadership to improve retention, renewal, and expansion outcomes through operational insights, reporting, and process optimization</div>

</li>

<li>

<div>Enable GTM readiness and operational execution for new product launches, packaging changes, pricing updates, and growth initiatives</div>

</li>

<li>

<div>Deliver executive-level reporting, business reviews, and performance insights that support decision-making across revenue leadership</div>

</li>

<li>

<div>Build, lead, and develop a high-performing Revenue Operations organization, driving operational excellence, scalable processes, and the adoption of AI-enabled solutions that improve productivity and business performance</div>

</li>

</ul>

<h2 class="p1"><span class="s1">Requirements</span></h2>

<ul>

<li>12+ years of experience in Revenue Operations, Sales Operations, GTM Operations, Finance, or related functions within a scaled SaaS or product-led growth company</li>

<li>Proven experience leading revenue operations for multi-segment B2B organizations across SMB, Mid-Market, and Enterprise customer segments</li>

<li>Deep expertise in forecasting, revenue planning, territory design, quota management, sales productivity, incentive compensation, and pipeline management</li>

<li>Strong understanding of SaaS business models, revenue motions, and key operational drivers across acquisition, expansion, and retention</li>

<li>Demonstrated ability to identify operational challenges and implement scalable, data-driven solutions that improve business performance</li>

<li>Strong cross-functional leadership skills with the ability to influence senior stakeholders across Sales, Finance, Product, Marketing, and Customer organizations</li>

<li>Experience supporting organizations through significant growth and GTM evolution, including PLG, sales-assisted, and enterprise motions</li>

<li>Strong analytical and problem-solving capabilities, with extensive experience leveraging data to drive operational and business decisions</li>

<li>Track record of building, developing, and leading high-performing revenue operations teams in a fast-paced, evolving environment</li>

</ul>

<h2>Preferred Qualifications</h2>

<ul>

<li>Proven track record implementing AI-enabled revenue solutions that deliver measurable improvements in efficiency, productivity, and business outcomes</li>

<li>Demonstrated experience owning and scaling GTM technology ecosystems, with deep expertise in Salesforce and related revenue platforms</li>

</ul>

<h2><span class=" author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qowz81zz86z7z65z9wz73z7z75z6emz81zz70z4oz65zrz86z4dnz72ztz67zvoz67zl91">Durable Skills</span></h2>

<p><span class=" author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qotuz85zdz87z113tz83zz67z5n8qpz80zpz89zoz69zcz76zz87zz88zz88z5gsnz85zu">AI fluency means using these tools to </span><span class=" author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qotuz85zdz87z113tz83zz67z5n8qpz80zpz89zoz69zcz76zz87zz88zz88z5gsnz85zu"><em>amplify</em></span><span class=" author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qotuz85zdz87z113tz83zz67z5n8qpz80zpz89zoz69zcz76zz87zz88zz88z5gsnz85zu"> human judgment, not replace it. We believe people with these skills will thrive as work and technology</span> <span class=" author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qotuz85zdz87z113tz83zz67z5n8qpz80zpz89zoz69zcz76zz87zz88zz88z5gsnz85zu">continue to evolve:</span></p>

<ul class="listtype-bullet listindent1 list-bullet1" data-testid="bullet-list" data-test-indentation="1">

<li><span class=" author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qotuz85zdz87z113tz83zz67z5n8qpz80zpz89zoz69zcz76zz87zz88zz88z5gsnz85zu"><strong>Awareness:</strong></span> <span class=" author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qotv4sz81zsz68zwz85z3z78zbz88z2z76zpz74z2v1z75zz67zz85zjlvz122zz122z6oaz84z">U</span><span class=" author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qotuz85zdz87z113tz83zz67z5n8qpz80zpz89zoz69zcz76zz87zz88zz88z5gsnz85zu">nderstand </span><span class=" author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qotv4sz81zsz68zwz85z3z78zbz88z2z76zpz74z2v1z75zz67zz85zjlvz122zz122z6oaz84z">yourself</span><span class=" author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qotuz85zdz87z113tz83zz67z5n8qpz80zpz89zoz69zcz76zz87zz88zz88z5gsnz85zu"> and others</span><span class=" author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qotv4sz81zsz68zwz85z3z78zbz88z2z76zpz74z2v1z75zz67zz85zjlvz122zz122z6oaz84z">.</span></li>

<li><span class=" author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qotuz85zdz87z113tz83zz67z5n8qpz80zpz89zoz69zcz76zz87zz88zz88z5gsnz85zu"><strong>Judgment:</strong></span> <span class=" author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qotv4sz81zsz68zwz85z3z78zbz88z2z76zpz74z2v1z75zz67zz85zjlvz122zz122z6oaz84z">E</span><span class=" author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qotuz85zdz87z113tz83zz67z5n8qpz80zpz89zoz69zcz76zz87zz88zz88z5gsnz85zu">valuat</span><span class=" author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qotv4sz81zsz68zwz85z3z78zbz88z2z76zpz74z2v1z75zz67zz85zjlvz122zz122z6oaz84z">e</span><span class=" author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qotuz85zdz87z113tz83zz67z5n8qpz80zpz89zoz69zcz76zz87zz88zz88z5gsnz85zu"> information and mak</span><span class=" author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qotv4sz81zsz68zwz85z3z78zbz88z2z76zpz74z2v1z75zz67zz85zjlvz122zz122z6oaz84z">e </span><span class=" author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qotuz85zdz87z113tz83zz67z5n8qpz80zpz89zoz69zcz76zz87zz88zz88z5gsnz85zu">decisions in complex situations</span><span class=" author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qotv4sz81zsz68zwz85z3z78zbz88z2z76zpz74z2v1z75zz67zz85zjlvz122zz122z6oaz84z">.</span></li>

<li><span class=" author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qotuz85zdz87z113tz83zz67z5n8qpz80zpz89zoz69zcz76zz87zz88zz88z5gsnz85zu"><strong>Adaptability:</strong></span> <span class=" author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qotv4sz81zsz68zwz85z3z78zbz88z2z76zpz74z2v1z75zz67zz85zjlvz122zz122z6oaz84z">L</span><span class=" author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qotuz85zdz87z113tz83zz67z5n8qpz80zpz89zoz69zcz76zz87zz88zz88z5gsnz85zu">earn, adjust, and stay effective through change</span><span class=" author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qotv4sz81zsz68zwz85z3z78zbz88z2z76zpz74z2v1z75zz67zz85zjlvz122zz122z6oaz84z">.</span></li>

<li><span class=" author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qotuz85zdz87z113tz83zz67z5n8qpz80zpz89zoz69zcz76zz87zz88zz88z5gsnz85zu"><strong>Connection:</strong></span> <span class=" author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qotv4sz81zsz68zwz85z3z78zbz88z2z76zpz74z2v1z75zz67zz85zjlvz122zz122z6oaz84z">C</span><span class=" author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qotuz85zdz87z113tz83zz67z5n8qpz80zpz89zoz69zcz76zz87zz88zz88z5gsnz85zu">ommunicat</span><span class=" author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qotv4sz81zsz68zwz85z3z78zbz88z2z76zpz74z2v1z75zz67zz85zjlvz122zz122z6oaz84z">e</span><span class=" author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qotuz85zdz87z113tz83zz67z5n8qpz80zpz89zoz69zcz76zz87zz88zz88z5gsnz85zu">, collaborat</span><span class=" author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qotv4sz81zsz68zwz85z3z78zbz88z2z76zpz74z2v1z75zz67zz85zjlvz122zz122z6oaz84z">e</span><span class=" author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qotuz85zdz87z113tz83zz67z5n8qpz80zpz89zoz69zcz76zz87zz88zz88z5gsnz85zu">, and build trust</span><span class=" author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qotv4sz81zsz68zwz85z3z78zbz88z2z76zpz74z2v1z75zz67zz85zjlvz122zz122z6oaz84z">.</span></li>

</ul>

<p><span class=" author-d-iz88z86z86za0dz67zz78zz78zz74zz68zjz80zz71z9iz90z9z84z5u1z69zz90zlz73z3ly1nz76zw1r5kz89zz66z4z65zz65zjz122zf092">To learn more about why these skills matter and what the data shows about thriving through change, read this </span><span class="attrlink url author-d-iz88z86z86za0dz67zz78zz78zz74zz68zjz80zz71z9iz90z9z84z5u1z69zz90zlz73z3ly1nz76zw1r5kz89zz66z4z65zz65zjz122zf092"><a class="attrlink" href="https://www.Dropbox.jobs/en/our-blog/employee-stories/the-era-of-durable-skills-what-the-data-tells-us-about-thriving-in-change/" target="_blank" data-target-href="https://www.Dropbox.jobs/en/our-blog/employee-stories/the-era-of-durable-skills-what-the-data-tells-us-about-thriving-in-change/">blog post</a></span> <span class=" author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qotuz85zdz87z113tz83zz67z5n8qpz80zpz89zoz69zcz76zz87zz88zz88z5gsnz85zu">from</span><span class=" author-d-iz88z86z86za0dz67zz78zz78zz74zz68zjz80zz71z9iz90z9z84z5u1z69zz90zlz73z3ly1nz76zw1r5kz89zz66z4z65zz65zjz122zf092"> our Chief People Officer, Melanie Rosenwasser.</span></p>

<h2 data-usually-unique-id="044234883370604133046166"><span class=" author-d-1gg9uz65z1iz85zgdz68zmqkz84zo2qowz81zqz90zkz74zz76zeez80zz68zz89zz88zvqz86zuxlz73zexxz80zz73z6d6z72zz79zsz77z">Compensation</span></h2>

Want to learn more about what it's like to work at Dropbox? View our full profile.

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Frequently Asked Questions About Working at Dropbox

Common questions candidates ask about this role and Dropbox's workplace

Dropbox is a cloud storage solution, equipped with features to help you save time, improve your productivity and collaborate with others.

This position is listed as remote based on the job location.

Salary information may vary by role and location. Please check the specific job listing or discuss compensation during the interview process.

Dropbox is an established organization in its industry. The company focuses on maintaining a supportive workplace culture for all employees.

Key benefit categories include: Health & Wellness, Financial & Retirement, Family Support, Time Off & Flexibility, Learning & Development. You can view more details on their CertCheck profile.

The day-to-day environment is guided by core values such as Connection Over Distance and Frictionless Execution and Creative Problem-Solving.

The company has committed to inclusive practices including: Empower Human-Centered Collaboration and Support Comprehensive Employee Wellbeing.

Dropbox has a supportive and collaborative culture, recognized as a loved place to work by its team members.

Dropbox currently has 30 open positions. They are hiring across departments like Direct Sales - AMER (Sub Team), Direct & Channel Sales, UKI (Sub Team), Partnership Management (Sub Team). You can view all current openings at certcheck.mostlovedworkplace.com/companies/dropbox/jobs.

The interview process typically involves an initial recruiter screen followed by team interviews. Please contact Dropbox's recruiting team for specific details on this role's process.

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