The Senior Director, Head of Dash Strategy will lead cross-functional teams, drive long-term strategy and execution plans, and align GTM and sales strategies.
Role Description
We’re hiring a Chief of Staff to the GM of Dash, Dropbox’s AI initiative reimagining the future of knowledge work. This is not a generalist support role. It’s a strategic, high-trust position designed to operate as an extension of the GM, shaping how Dash grows, scales, and wins.
You’ll partner closely with the GM to drive long-term clarity, resolve cross-functional ambiguity, and scale strategic decision-making across EPD (Engineering, Product, Design) and business leadership. This role is for someone who has built before—ex-founders, product leaders, and operator-strategists who understand how to scale complex orgs, shape product direction, and align enterprise momentum.
You’ll serve as the connective tissue between product, strategy, and the executive layer, helping steer Dash’s evolution, align vision with execution, and drive forward our most important bets.
ResponsibilitiesStrategic Partnership to GM
- Operate as a right hand to the GM—filtering enterprise noise, shaping priorities, and accelerating strategic decisions
- Drive long-range clarity and tradeoff frameworks across EPD, Sales, and GTM
- Own strategic communications and narrative development for Dash LT, CEO, Board, and S-team
Product-Centric Strategy & Portfolio Shaping
- Lead multi-year strategic planning, business modeling, and scenario design across the Dash business
- Shape investment themes and portfolio direction in close collaboration with Product and Design leaders
- Incubate and lead 0→1 initiatives, including market explorations, business model pivots, and M&A assessments
Cross-Functional Cohesion
- Align product strategy with company-wide goals, org shape, and enterprise priorities
- Orchestrate executive-level coordination across forums (e.g., roadmap checkpoints, investment reviews, Switchboard)
- Help shape and advise on senior hiring decisions and org design in alignment with strategic goals
Strategic Narrative & External Leverage
- Craft crisp, compelling narratives for strategic forums—connecting market insight, product vision, and business priorities
- Represent the GM in executive, customer, or partner engagements, driving high-context product and business discussions
Launch & Readiness Alignment
- Collaborate with GTM and sales leadership to ensure product readiness for launches or strategic pivots—without owning day-to-day GTM ops
- Connect product decisions to enterprise goals with strategic coherence and speed
- 10–15 years of experience in product management, engineering and/or founder/operator roles
- Experience building and scaling product orgs; founder or early-stage operator backgrounds strongly preferred
- Strategic systems thinker, comfortable with financial modeling, planning, investment frameworks
- Executive communicator, able to write 1.0-level docs, craft narratives, and lead CEO/Board-level conversations
- Independent and high-leverage contributor—able to lead from ambiguity to clarity with minimal oversight
- Deep comfort working with senior leadership and operating in high-trust, high-stakes environments
- Located in San Fransisco Bay Area
- Familiarity with GTM, ARR modeling, or sales strategy is a plus, but not required.
US Zone 1
$246,100—$332,900 USD
US Zone 2
$221,500—$299,700 USD
US Zone 3
$196,900—$266,300 USD
Dropbox Los Angeles, California, USA Office
Los Angeles, CA, United States
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