Director of Pricing and Packaging

As Director of Pricing and Packaging at Dropbox, you will lead the strategy that determines how we package, price, and monetize our products across product-led growth (PLG) and sales-led growth (SLG) motions. Reporting to Head of Product Marketing, you will lead a small team and partner closely with Product, Finance, Sales, Marketing, Data Science, and senior executives to make pricing and packaging a durable driver of customer value and profitable growth.

This is a highly visible opportunity to help reinvent Dropbox’s monetization approach as we expand our sales-led business and build for the AI era. You will develop a holistic pricing and packaging architecture across products, customer segments, and routes to market—balancing customer adoption, competitive positioning, revenue growth, cost to serve, and margin. You will translate complex analysis into clear strategic choices, build alignment among senior leaders, and establish the capabilities and operating rhythms needed to make consistently strong monetization decisions.

You will have significant exposure to Dropbox’s senior leadership team and the opportunity to shape some of the company’s most consequential growth decisions. Your work will directly influence how customers experience and value Dropbox, how our products go to market, and how the business grows over the long term.

• Define and lead Dropbox’s company-wide pricing and packaging strategy across PLG and SLG motions, customer segments, product portfolios, and geographies.
• Design the next generation of Dropbox’s packaging and monetization architecture, including approaches for AI-powered products and capabilities, while balancing customer value, adoption, revenue, cost to serve, and margin.
• Build rigorous business cases and financial models to evaluate pricing and packaging opportunities, incorporating demand, willingness to pay, competitive dynamics, usage patterns, unit economics, and potential customer and revenue impacts.
• Partner with Product, Finance, Sales, Marketing, Data Science, and Operations leaders to translate strategy into executable plans, including research, experimentation, rollout, enablement, measurement, and iteration.
• Advise senior executives on high-impact monetization decisions by synthesizing complex quantitative and qualitative evidence into clear recommendations, tradeoffs, and decision frameworks.
• Establish pricing and packaging governance, operating rhythms, performance metrics, and experimentation practices that improve the quality and speed of decision-making across Dropbox.
• Lead, develop, and inspire a small team of pricing and packaging professionals while expanding the organization’s broader monetization capabilities.

• 10+ years of experience in pricing, packaging, monetization, growth strategy, strategic finance, product strategy, management consulting, or a related discipline, including substantial experience in B2B SaaS.
• Demonstrated experience developing and implementing pricing or packaging strategies that produced measurable business or customer outcomes.
• Experience with both product-led and sales-led business models, including an understanding of their distinct customer journeys, routes to market, and monetization considerations.
• Experience building pricing business cases and financial models that connect customer behavior and willingness to pay with revenue, cost to serve, unit economics, and margin.
• Working knowledge of SaaS and AI monetization models, including subscription, seat-based, usage-based, consumption-based, and hybrid approaches.
• Demonstrated ability to influence executive-level decisions and align senior cross-functional stakeholders around complex, high-impact initiatives.
• People-management experience, including hiring, coaching, and developing high-performing team members.

• Experience leading a major pricing or packaging transformation for a multi-product or global SaaS company.
• Experience developing monetization strategies for AI-powered products, including evaluating inference or infrastructure costs, usage economics, value metrics, and margin implications.
• Experience managing the intersection of self-serve, enterprise, and partner-led offerings within a shared product portfolio.
• Experience with pricing research and experimentation methods such as conjoint analysis, willingness-to-pay research, price elasticity analysis, customer segmentation, or controlled testing.

AI fluency means using these tools to amplify human judgment, not replace it. We believe people with these skills will thrive as work and technology continue to evolve:

• Awareness: Understand yourself and others.
• Judgment: Evaluate information and make decisions in complex situations.
• Adaptability: Learn, adjust, and stay effective through change.
• Connection: Communicate, collaborate, and build trust.

To learn more about why these skills matter and what the data shows about thriving through change, read this blog post from our Chief People Officer, Melanie Rosenwasser.