Dropbox Director Pricing - AI Monetization Strategy Role

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

Job summary

Dropbox is seeking a Director of Pricing and Packaging to shape monetization across PLG and SLG motions from a remote US base. You will partner with Product, Finance, Sales and Marketing to craft AI-focused pricing architectures and durable monetization strategies for a multi-product portfolio.

You will lead a small team, translate complex analytics into strategic guidance, and collaborate with senior leadership to drive sustainable revenue growth while balancing customer value and margin in a

Qualifications

• 10+ years in pricing, packaging, monetization, growth strategy or related fields in B2B SaaS

Responsibilities

• Define and lead company-wide pricing and packaging strategy across PLG and SLG motions, segments, portfolios, and geographies.
• Design next-gen packaging and monetization architecture for AI-powered products balancing value, adoption, revenue and margin.
• Build rigorous business cases and financial models incorporating demand, willingness to pay, competition, usage, unit economics.
• Partner with senior leaders to translate strategy into executable plans, including research, rollout, enablement, measurement and iteration.
• Advise executives with synthesized insights and clear recommendations, tradeoffs, and decision frameworks.
• Establish governance, rhythms, metrics and experimentation practices to improve monetization decision speed.
• Lead and develop a small pricing/packaging team and grow monetization capabilities across the org.

Skills

AI monetization strategy

PLG and SLG pricing

Executive-level financial modeling

Cross-functional leadership

Job description

Dropbox Director Pricing - AI Monetization Strategy Role — Remote

Career trajectory: The Director of Pricing and Packaging at Dropbox is a high-visibility, high-impact role that sits at the intersection of Product Marketing, Finance, and Strategy. Reporting directly to the Head of Product Marketing with regular exposure to senior executives, this is a clear path to VP-level monetization or Chief Strategy Officer roles at SaaS companies.

Compensation vs. market: At $253K–$342K (Zone 1), this is well-aligned with Director/Senior Director-level compensation at large-cap SaaS companies. Industry benchmarks for similar roles at companies like Salesforce, HubSpot, or Adobe typically range $220K–$320K total cash, so Dropbox's range is competitive at the upper end.

Skills you will build:

• AI monetization strategy — one of the most in-demand skill sets in SaaS right now
• PLG and SLG dual-motion pricing architecture
• Executive-level financial modeling and storytelling
• Cross-functional leadership across Product, Finance, Sales, and Marketing

Green flags: Dropbox's explicit investment in AI-era reinvention signals real budget and mandate behind this role. The "small team" framing suggests high ownership with minimal bureaucracy. The "Durable Skills" framework hints at a psychologically aware, forward-thinking culture.

Potential red flag: Dropbox has undergone significant restructuring and layoffs in recent years. Candidates should probe for team stability and long-term product investment priorities during interviews.

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 the 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.

Responsibilities

• 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.

Requirements

• 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.

Preferred Qualifications

• 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.

Is the Director of Pricing and Packaging role at Dropbox fully remote? Yes, Dropbox operates under a Virtual First model, making this role primarily remote. However, it is restricted to candidates in the United States, with compensation varying by geographic zone. What is the salary range for this role at Dropbox? Compensation is tiered by US geography: Zone 1 pays $253,300–$342,700, Zone 2 pays $228,000–$308,400, and Zone 3 pays $202,600–$274,200 USD annually. How much experience is required for this position? Dropbox requires 10+ years of experience in pricing, packaging, monetization, growth strategy, strategic finance, or a related discipline, with substantial B2B SaaS experience. Will this role involve working with AI products? Yes, a key focus of the role is designing monetization architecture for AI-powered products, including evaluating inference costs, usage economics, and value metrics as Dropbox builds for the AI era. Does this role involve managing a team? Yes, you will lead a small team of pricing and packaging professionals and are expected to hire, coach, and develop high-performing team members.

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