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Dropbox

Cloud storage, file sync, collaboration platform

Vice President of Revenue Operations

Full-Time
$348.5k - $471.5k
Expert
Remote in USA
Remote
Sales & Account ManagementSales Operations
Company Historically Provides H1B Sponsorship

About the job

Requirements
  • 15+ years of experience in Revenue Operations, Sales Operations, GTM Operations, Finance, or related functions within a scaled SaaS or product-led growth company.
  • Proven experience leading revenue operations for multi-segment B2B organizations across SMB, Mid-Market, and Enterprise customer segments.
  • Deep expertise in forecasting, revenue planning, territory design, quota management, sales productivity, incentive compensation, and pipeline management.
  • Strong understanding of SaaS business models, revenue motions, and key operational drivers across acquisition, expansion, and retention.
  • Demonstrated ability to identify operational challenges and implement scalable, data-driven solutions that improve business performance.
  • Strong cross-functional leadership skills with the ability to influence senior stakeholders across Sales, Finance, Product, Marketing, and Customer organizations.
  • Experience supporting organizations through significant growth and GTM evolution, including PLG, sales-assisted, and enterprise motions.
  • Strong analytical and problem-solving capabilities, with extensive experience leveraging data to drive operational and business decisions.
  • Track record of building, developing, and leading high-performing revenue operations teams in a fast-paced, evolving environment.
Responsibilities
  • Define and lead Dropbox’s global revenue operating strategy, ensuring the company’s GTM model is designed to support long-term growth, efficiency, and increasing enterprise complexity.
  • Serve as a strategic advisor to the Chief Business Officer and executive leadership team, bringing data-driven insights and recommendations to critical decisions around growth, investment, resource allocation, organizational design, and GTM strategy.
  • Own the end-to-end revenue operating model across Sales, Marketing, Customer Success, and Support, including segmentation, coverage models, territory architecture, role design, operating rhythms, and cross-functional accountability.
  • Lead company-wide annual and long-range revenue planning, including bookings targets, quota strategy, capacity and workforce planning, territory design, productivity assumptions, investment scenarios, and resource allocation.
  • Establish a forecasting and pipeline management framework that increases predictability, strengthens executive visibility, and enables earlier intervention against business performance risks.
  • Define and evolve the company’s revenue performance architecture, including the KPIs, operating cadences, inspection mechanisms, and executive business reviews used to assess growth, productivity, efficiency, retention, and expansion.
  • Lead Revenue Operations across the full customer lifecycle, creating scalable and integrated processes from demand generation and lead management through opportunity conversion, renewal, expansion, and customer growth.
  • Partner with Marketing leadership to oversee Marketing Operations and align demand generation investments, pipeline creation, segmentation, campaign performance, and downstream revenue outcomes.
  • Partner with Finance on revenue strategy and planning, pricing and packaging operations, investment allocation, deal governance, incentive compensation, and performance management.
  • Partner with Product and GTM leadership to define the operating strategy for new products, new customer segments, pricing changes, packaging evolution, and emerging sales motions.
  • Own the strategy and evolution of Dropbox’s GTM technology ecosystem, ensuring systems, data architecture, automation, and workflows scale effectively with the business.
  • Lead the adoption of AI across Revenue Operations and the broader GTM organization, identifying opportunities to improve seller productivity, forecasting, customer targeting, planning, decision-making, and operational efficiency.
  • Simplify legacy processes, systems, and organizational structures where needed, driving enterprise-wide transformation and change management across a complex stakeholder environment.
  • Build, lead, and develop the Revenue Operations organization, including leadership succession, organizational design, talent development, and clear accountability across teams.
  • Represent Revenue Operations in executive-level and company-wide planning forums, serving as a trusted voice on GTM performance, risks, opportunities, and operating priorities.
Desired Qualifications
  • Proven track record implementing AI-enabled revenue solutions that deliver measurable improvements in efficiency, productivity, and business outcomes.
  • Demonstrated experience owning and scaling GTM technology ecosystems, with deep expertise in Salesforce and related revenue platforms.

About the company

Dropbox provides cloud storage and file synchronization for individuals and organizations, with features for storing, sharing, and collaborating on documents. Users upload files to online storage; the service syncs them across devices and makes them available in shared workspaces, with links, comments, and real-time collaboration. It differentiates itself with a simple interface, strong security, reliable syncing, and a growing ecosystem of integrations and partnerships including DocSend and HelloSign. Its goal is to support remote and distributed teams by offering a straightforward, secure way to access and work on files from anywhere while growing its subscription revenue.

Company Size

1,001-5,000

Company Stage

IPO

Headquarters

San Francisco, California

Founded

2007

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Simplify's Take

What believers are saying

  • Q2 2026 revenue reached $631.5 million, with ARR rising to $2.566 billion.
  • Management raised 2026 operating margin guidance to 40.0%-40.5% and uFCF to $1.07 billion.
  • Dash rollout now offsets FormSwift drag and supports higher monetization across Teams.

What critics are saying

  • Core revenue barely grew 0.9% in Q2 2026, exposing mature demand.
  • Google Workspace and Microsoft 365 can absorb Dropbox's remaining use case by 2027.
  • Dropbox's secured collateral and leverage covenants amplify downside if buybacks outrun growth.

What makes Dropbox unique

  • Dropbox Dash for Business unifies search, sharing, and access controls across connected apps.
  • Remote-first operations attract talent: 74% of 2026 hires cited virtual-first as reason.
  • Secured credit plus $1.2 billion buybacks signal disciplined cash generation and capital returns.

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Benefits

  • Competitive medical, dental & vision coverage
  • Competitive 401(k) Plan with a generous company match & immediate vesting
  • Flexible Time Off/Paid Time Off
  • 11 Company-wide PTO days
  • Volunteer time off and more
  • Life Insurance, Disability Insurance & Travel benefit plans
  • Perks Allowance
  • Parental benefits
  • Mental Health & Wellness benefits
  • Free Dropbox space for your friends and family

Growth & Insights and Company News

Headcount

6 month growth

2%

1 year growth

2%

2 year growth

0%
Tech in Asia
Oct 12th, 2026
Dropbox launches Protect in Singapore to govern file access across Drive and Microsoft 365

Dropbox has launched Dropbox Protect in Singapore, a data access governance tool that shows information technology and security teams who can access content across Dropbox, Google Drive, and Microsoft 365. The tool lets teams review public links, external collaborators, and risky permissions. They can also automate policies, alerts, and access fixes, and generate reports and audit logs for governance and compliance. The launch comes as Singapore's Personal Data Protection Act requires organisations to make reasonable security arrangements against unauthorised access to, or disclosure of, personal data held electronically. Dropbox Protect competes with data access governance vendors, including tools covering Google Drive and SharePoint. Microsoft also offers governance actions in Defender for Cloud Apps.

Fortune
Oct 7th, 2026
Dropbox CTO pushes full AI adoption across 2,113 employees with bottom-up approach

Dropbox CTO Ali Dasdan is driving AI adoption across the company's 2,113 employees. When he joined in March 2025, less than 40% of engineering, product, and design teams used AI tools. Through training, hackathons, and championing superusers, he achieved full adoption among these groups. The company has made ChatGPT Enterprise widely available to knowledge workers and approved AI features in platforms like Workday, Slack, and Zoom. Non-technical staff use tools like Lovable to create custom applications, with hundreds now deployed across departments. Dasdan says AI enables faster customer support and helps clear technical debt. The company has focused on enhancing Dash, its AI-powered search tool, with improved capabilities for indexing and searching images and video. Dropbox has also integrated Dash into ChatGPT, Claude, and Google Gemini ecosystems to meet customers where they already work.

Yahoo Finance
Sep 16th, 2026
Dropbox co-CEO sells 28,800 shares for $1M as stock generates 15% annual return

Dropbox co-CEO Ashraf Alkarmi sold 28,800 shares of Class A Common Stock for $1 million on 11 September 2026, according to an SEC filing. The sale was executed through a Rule 10b5-1 trading plan established on 12 June 2026, which allows insiders to make pre-scheduled trades. Following the transaction, Alkarmi retains 1,004,081 shares, representing approximately 0.39% of the company. The stock had generated a 15% one-year return as of the transaction date. As of 15 September 2026, Dropbox shares traded at $37.63, giving the San Francisco-based software company a market capitalisation of $9.5 billion. The company reported trailing twelve-month revenue of $2.5 billion and net income of $442.8 million.

Yahoo Finance
Aug 23rd, 2026
Dropbox CFO sells $25M in shares days after raising guidance

Dropbox CFO Ross Tennenbaum sold 20,326 shares of Class A Common Stock on 17 August, according to an SEC Form 4 filing. The transaction, valued at $25.34 million, was executed for tax purposes and does not reflect a change in the insider's assessment of the company's valuation. Tennenbaum continues to hold 759,000 shares directly, valued at $25.7 million based on the 18 August closing price. He also holds restricted stock units scheduled to vest through 15 November 2029, contingent upon continued service. Dropbox operates a software-as-a-service business model, generating revenue through tiered subscription plans for individual users, teams, and enterprises. The company has a market capitalisation of $8.6 billion and reported $2.5 billion in trailing twelve-month revenue.

Yahoo Finance
Aug 23rd, 2026
Dropbox CTO sells $1M in shares under pre-scheduled trading plan from May 2025

Dropbox CTO Ali Dasdan sold 30,587 Class A shares on 17-18 August, worth approximately $1 million, according to an SEC filing. The transaction included 19,255 shares withheld for taxes and 11,332 shares sold through a pre-scheduled trading plan. The tax withholding was a non-discretionary transaction triggered by vesting equity awards. The share sale was executed under a Rule 10b5-1 plan Dasdan adopted on 12 May 2025, allowing insiders to establish predetermined selling schedules for liquidity or diversification whilst maintaining regulatory compliance. Following the disposition, Dasdan holds 471,052 shares directly, representing a 6% decrease from his previous position of 501,639 shares. His remaining direct equity interest is valued at roughly $15.95 million and represents approximately 0.2% of the company. These holdings include restricted stock units scheduled to vest through 15 November 2030.