Role Description

We’re hiring a Senior Director, Head of Dash Strategy to help steer the long-term growth and direction of our business. This is a leadership role within the Team of Dash Operations, designed to give enterprise leverage across both the Dash EPD & Dash GTM teams.

You’ll operate as a strategic partner to two leaders—connecting market insight to organizational direction, helping shape integrated product and go-to-market strategies, and serving as the connective tissue between cross-functional priorities. This is a specialized role rooted in long-range clarity, GTM readiness, execution acceleration, and VP/GM leverage, not generalist support.

You’ll manage with a group of Chiefs of Staff to EPD and GTM/Sales who manage Dash’s day-to-day operating system. Your domain is long-term strategy, executive leverage, enterprise planning, and GTM enablement, focused on what to prioritize and why, while the CoS drives how to execute and track.

Responsibilities

Cross-Functional Leadership & Integration

• Lead a small squad of Chiefs of Staff to VPs and Program Managers to enable cross-org alignment.
• Act as strategic partner and delegate to the GM and VP of Product & GTM, ensuring clarity and cohesion across Product, Sales, and Marketing.
• Drive coordination and alignment across teams; translate high-level vision into clear, actionable strategic plans. Unblock ambiguity and resolve complex cross-functional challenges with speed and insight.

Long-Term Planning & Strategic Modeling

• Lead multi-year and annual budget planning/ownership, scenario modeling, and enterprise-level prioritization across product and GTM.
• Synthesize market trends, competitive dynamics, and emerging GTM opportunities into actionable business strategy.
• Inform portfolio investments, strategic themes, and resourcing decisions at the GM and VP level.

GTM & Sales Strategy

• Partner with GTM and Sales leaders to ensure product launches, GTM, and Sales strategies are ready and resourced.
• Drive launch planning and readiness alignment; assess and address gaps across marketing, sales, and enablement.
• Connect product direction to enterprise revenue goals with cross-functional fidelity.

Execution Acceleration & Strategic Projects

• Drive high-leverage strategic initiatives—from identifying priority bets to leading 0→1 incubations, market explorations, and business model innovations as a delegate of the GM and VP.
• Shape and accelerate strategic decision-making and remove execution bottlenecks.
• Champion excellence in business rhythms, collaboration, and execution standards.

Strategic Communication & Narrative

• • Craft crisp, compelling narratives that unify strategic vision, external insight, and internal priorities.
  • Prepare high-impact updates and strategic materials for the CEO, S-team, and Board.
  • Lead strategic inputs for executive forums including Switchboard, investment reviews, and roadmap checkpoints.

Requirements

• 10–15 years in product management, business operations, strategy, or consulting
• Deep experience navigating complex orgs and aligning cross-functional stakeholders
• Strong analytical, modeling, and systems thinking skills
• Experience in GTM, sales strategy, market analysis, or M&A preferred
• Strategic communicator with executive presence and clarity
• Exceptional written and verbal communication skills — able to distill complexity and drive clear decisions at the exec level

Preferred Qualifications

• A background in strategy consulting, pricing and packaging strategy, and/or change-management
• SaaS industry experience
• Resides in California, Bay Area strongly preferred

Compensation

Company Description

Dropbox isn’t just a workplace—it’s a living lab for more enlightened ways of working. We're a global community of bold visionaries and resourceful doers who are shaping the future of Dropbox—and with it the future of work. Our Virtual First model combines the autonomy of a distributed workplace with the power of human connection, making space for both meaningful work and meaningful relationships. With our start-up mindset and enterprise-level opportunities, you can be who you are and grow into who you’re meant to be. Here, you can own your impact to make work more intuitive, joyful, and human—for you as a Dropboxer and for hundreds of millions of people worldwide. If you're ready to push boundaries—and yourself— Dropbox is ready for you.

Team Description

The Dropbox Product Management Team envisions and builds the future of work while growing our business, one product at a time. We're strategic thinkers and advocates for our users, crafting solutions that make work more intuitive and joyful. Using data, research, and strategy—and a healthy dose of empathy—we guide cross-functional teams toward the shared goal of creating transformative products that people love to use. If you're passionate about building solutions that reshape how the world works while delighting users in the process, join our Product Management team. Areas of work include Product Management, Product Strategy, User Research, Data Analytics, Product Operations, Growth Strategy, and Go-to-Market Planning.

Dropbox is an equal opportunity employer. We are a welcoming place for everyone, and we do our best to make sure all people feel supported and connected at work. A big part of that effort is our support for members and allies of internal groups like Asians at Dropbox, BlackDropboxers, enABLE, TODOS (Latinx), Pridebox (LGBTQ), Vets at Dropbox, and Women at Dropbox.