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Dropbox // cloud storage
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Role Description

Dropbox is hiring a Chief of Staff to support the VP of Product & Go-to-Market for Dropbox Dash, our AI-powered work assistant.

In this role, youll be managing alignment, momentum, & execution across a fast-moving, cross-functional organization.

This is a career-defining opportunity for a high-ownership, product-minded operator who wants a front-row seat to executive decision-making, cross-functional strategy, & business leadership at scale.

If youve shipped products, led GTM initiatives, & are ready to accelerate into an executive leadership path, this is your launchpad.

Why This Role

  • Impact: Directly shape how Dropbox Dash is built, launched, & scaled.
  • Visibility: Work closely with senior leadership & get exposure across the business.
  • Growth: Build a rare skillset at the intersection of product, GTM, & executive operations.
  • Trajectory: This role is a launchpad to future leadershipGM, Head of Product, or VP.

At Dropbox, we value speed, ownership, & continuous improvement. We focus on results, we play to winand we do it together.

Responsibilities

  • Strategic Partner & Proxy: Act as a trusted thought partner & proxy for the VP of Product & GTM - help drive clarity, decision-making, & alignment across the org. Translate high-level strategies into clear, actionable operating plans.
  • Execution & Follow-Through: Identify bottlenecks, unblock teams, & prioritize high-leverage initiatives. Ensure consistent follow-through & accelerate progress toward key outcomes with a strong bias for action.
  • Operating Cadence Leadership: Shape & own the business rhythms that drive focus & accountability - QBRs, roadmap reviews, weekly priorities, launch planning, & leadership team meetings. Champion operational excellence across the org.
  • Communication & Visibility: Craft crisp, high-impact communications executive updates, internal team narratives, & strategic reporting that elevate visibility & showcase the orgs impact. Turn complexity into clarity.
  • Cross-Functional Alignment: Act as the connective tissue across Product, Design, Marketing, & GTM. Drive org-wide coordination & ensure the team is focused on what matters most.
  • Ambiguity & Problem Solving: Lead & resolve cross-functional challenges often ambiguous or unstructured with speed, sound judgment, & strategic insight.
  • Culture & Team Effectiveness: Support & cultivate a high-performing, low-ego team culture. Build systems for learning, recognition, & continuous improvement that reinforce execution excellence & collective success.

Requirements

  • 6+ years of experience in product management, strategy, or business operations at a high-growth technology company
  • Proven product management experience with a track record of shipping products & driving cross-functional execution
  • Demonstrated success partnering directly with senior executives on planning, operating cadences, & strategic communication
  • Strong product sense & comfort navigating ambiguity & complexity
  • Confident decision-maker with a bias for action & a high-ownership mindset
  • Strong operational rigor with a hands-on, sleeves-rolled-up approach to solving problems
  • Excellent communicator who can distill complexity, align stakeholders, & drive clarity
  • Prior experience in SaaS or similarly scaled product-led environments

Preferred Qualifications

  • MBA or equivalent a plus
  • Familiarity with AI products
  • Experience designing or running OKR & operating cadence systems
  • Demonstrated experience leveraging AI tools in the flow of work 

Compensation

Canada Pay Range

 
 
 
 
 
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