Head of Pricing & Monetization Strategy

Dropbox; United States; Remote; USD 253,000 - 343,000; Full time

Job summary

Dropbox is seeking a Director of Pricing and Packaging to lead the strategy for packaging, pricing, and monetization across both product-led and sales-led motions. You will collaborate with Product, Finance, Sales, Marketing, Data Science, and senior leadership to ensure pricing drives customer value and profitable growth.

This role involves building a holistic pricing architecture across products, segments, and routes to market, balancing customer adoption with margin, translating complex

Qualifications

• 10+ years in pricing, packaging, monetization, or related fields with B2B SaaS experience.
• Experience creating and implementing pricing/packaging strategies with measurable outcomes.
• Experience with both product-led and sales-led models and customer journeys.
• Ability to build pricing business cases linking willingness to pay, revenue, and margin.
• Familiarity with SaaS and AI monetization models (subscription, usage-based, hybrid).
• Strong track record influencing executive decisions and aligning stakeholders.
• People management experience, including coaching and developing teams.

Responsibilities

• Define and lead company-wide pricing and packaging strategy across PLG and SLG motions, segments, products, and geographies.
• Design next-gen pricing and monetization architecture, including AI-powered products, balancing value, adoption, revenue, cost to serve, and margin.
• Build robust business cases and financial models to evaluate opportunities and impact on revenue and margins.
• Partner with Product, Finance, Sales, Marketing, Data Science, and Operations to translate strategy into executable plans.
• Advise executives with clear recommendations and decision frameworks based on quantitative and qualitative evidence.
• Establish governance, operating rhythms, and metrics to improve decision quality and speed.
• Lead and develop a small pricing/packaging team and expand monetization capabilities across the org.

Skills

Pricing strategy

Executive influence

Cross-functional leadership

Monetization models

PLG & SLG knowledge

Financial modeling

Job description

Dropbox is seeking a Director of Pricing and Packaging to lead the strategy for packaging, pricing, and monetization across both product-led and sales-led motions. You will collaborate with Product, Finance, Sales, Marketing, Data Science, and senior leadership to ensure pricing drives customer value and profitable growth.

This role involves building a holistic pricing architecture across products, segments, and routes to market, balancing customer adoption with margin, translating complex