Chief of Staff – VP of Product & Go-to-Market

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, you’ll be managing alignment, momentum, and 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, and business leadership at scale.

If you’ve shipped products, led GTM initiatives, and 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, and scaled.
• Visibility: Work closely with senior leadership and get exposure across the business.
• Growth: Build a rare skillset at the intersection of product, GTM, and executive operations.
• Trajectory: This role is a launchpad to future leadership—GM, Head of Product, or VP.

At Dropbox, we value speed, ownership, and continuous improvement. We focus on results, we play to win—and we do it together.

Responsibilities

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

Compensation