Dropbox

Senior Director, Head of Dash Strategy

Job Posted 1 day ago

Job Type

Remote

Location

Remote - US: San Francisco, CA

Experience

Senior

Category

Executive & Leadership

Job Description

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

US Zone 1
$291,600$394,400 USD
US Zone 2
$262,400$355,000 USD
US Zone 3
$233,200$315,600 USD

Ready for Your Next Step?

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