[All remote jobs](https://jobicy.com/jobs.md)[![Dropbox logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2020/09/WRILS-200923071227-398427.jpg)](https://jobicy.com/company/dropbox.md)[Dropbox](https://jobicy.com/company/dropbox.md) # Director of Pricing and Packaging AI Summary Dropbox is seeking a senior pricing and packaging leader to define monetization strategy across product-led and sales-led SaaS motions. The role owns pricing architecture, business cases, experimentation, governance, and executive recommendations across products, customer segments, and geographies. It requires close partnership with Product, Finance, Sales, Marketing, Data Science, and Operations, as well as leadership of a small specialized team. The director will shape AI product monetization while balancing customer value, adoption, unit economics, revenue growth, and margin.[Apply for this job](#job-application)[View company](https://jobicy.com/company/dropbox.md)ShareRemote from[USA](https://jobicy.com/job-region/usa.md)SalaryUSD 202,600–342,700 / yrDepartment[Product & Operations](https://jobicy.com/categories/management.md)EmploymentFull TimeExperienceDirectorPublished8 Nov 2026Apply before8 Dec 2026Listing views30Application actions2Application toolkit ## Make your next move. Prepare your resume, explore your fit, and draft a cover letter for this opportunity. Opportunity details ## About this role. ### Role Description As Director of Pricing and Packaging at [Dropbox](https://jobicy.com/company/dropbox.md), 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. ### 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. ### Durable Skills 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](https://www.dropbox.jobs/en/our-blog/employee-stories/the-era-of-durable-skills-what-the-data-tells-us-about-thriving-in-change/) from our Chief People Officer, Melanie Rosenwasser. ### Compensation US Zone 1 $253,300—$342,700 USD US Zone 2 $228,000—$308,400 USD US Zone 3 $202,600—$274,200 USD Show more [Apply now >](https://jobicy.com/jobs/159848-director-of-pricing-and-packaging.md) * ![Upload CV](data:image/svg+xml;base64,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) ### Upload your resume now To unlock remote work opportunities and be discovered by global employers. This job listing has been manually reviewed by the Jobicy Trust & Safety Team for compliance with our posting guidelines, including verification of the company's legitimacy, accuracy of job details, clarity of remote work policy, and absence of misleading or fraudulent content. ## Role DNA A quick view of the complexity, pace, ownership and collaboration implied by the job description. ### Job Complexity 5/5EasyHard ### Pace & Pressure 5/5RelaxedFast-paced ### Autonomy Level 5/5GuidedFull ownership ### Communication Load 5/5IndependentCollaborative AI insightThis is a high-impact director role requiring deep B2B SaaS monetization expertise, sophisticated financial modeling, and influence over executive-level decisions. The scope spans multiple go-to-market models, global packaging decisions, and emerging AI cost and value economics. ## Salary analysis Estimated compensation compared with the broader US market for similar roles. Estimated job median (per year)Market rate$272,650US market range (per year)$220k–$360k0$396.00k AI insightThe yearly pay period is inferred from the job context; it was not explicitly stated by the employer. The employer discloses annual USD base-pay ranges by US compensation zone, spanning $202,600 to $342,700. The overall midpoint is $272,650 per year. A reasonable estimated US market range for a director-level SaaS pricing and packaging leader is $220,000–$360,000 annually; these market figures are AI estimates, not verified salary research. ## Core skills Skills and capabilities most closely associated with this opportunity. [Pricing strategy](https://jobicy.com/jobs?search_keywords=Pricing%20strategy.md)[Product packaging](https://jobicy.com/jobs?search_keywords=Product%20packaging.md)[SaaS monetization](https://jobicy.com/jobs?search_keywords=SaaS%20monetization.md)[Financial modeling](https://jobicy.com/jobs?search_keywords=Financial%20modeling.md)[Unit economics](https://jobicy.com/jobs?search_keywords=Unit%20economics.md)[Price elasticity analysis](https://jobicy.com/jobs?search_keywords=Price%20elasticity%20analysis.md)[Willingness-to-pay research](https://jobicy.com/jobs?search_keywords=Willingness-to-pay%20research.md)[Go-to-market strategy](https://jobicy.com/jobs?search_keywords=Go-to-market%20strategy.md)[Product-led growth](https://jobicy.com/jobs?search_keywords=Product-led%20growth.md)[Sales-led growth](https://jobicy.com/jobs?search_keywords=Sales-led%20growth.md)[AI monetization](https://jobicy.com/jobs?search_keywords=AI%20monetization.md)[Cross-functional leadership](https://jobicy.com/jobs?search_keywords=Cross-functional%20leadership.md)[Executive stakeholder management](https://jobicy.com/jobs?search_keywords=Executive%20stakeholder%20management.md)[People management](https://jobicy.com/jobs?search_keywords=People%20management.md) Sample interview questionsHow would you develop a pricing and packaging strategy for an AI-powered SaaS capability with meaningful inference costs?I would begin with customer segmentation, jobs-to-be-done research, and willingness-to-pay evidence to identify the value metric customers understand. I would model adoption, usage, infrastructure costs, gross margin, and cannibalization under subscription, seat-based, usage-based, and hybrid options. I would then test prioritized hypotheses through controlled experiments and recommend a scalable package design with clear guardrails. Describe how you would align Product, Sales, Finance, and Marketing around a contentious pricing decision. I would establish a shared decision framework that makes customer impact, revenue upside, margin implications, operational complexity, and strategic risks explicit. Each function would contribute evidence within its domain, while I would synthesize the tradeoffs into a small number of actionable options. I would seek executive alignment on the decision criteria, owner, rollout milestones, and success metrics before implementation. What metrics would you use to evaluate whether a new packaging structure is successful? I would track conversion, expansion, retention, adoption of targeted capabilities, average revenue per account, gross margin, discounting behavior, and customer support or sales friction. The metrics should be segmented by customer type, route to market, and legacy versus new cohorts. I would also monitor unintended effects such as downgrades, churn, or product adoption barriers. How do product-led growth and sales-led growth affect pricing and packaging choices? PLG packages should be easy to understand, discover, trial, and purchase with low friction, often using transparent value thresholds and self-serve upgrade paths. SLG packages can address more complex enterprise needs such as governance, administration, security, implementation, and committed usage. A strong shared architecture preserves coherent customer progression while allowing each motion to monetize its distinct value drivers. Tell us about a time you used analysis to change an executive-level monetization decision. A strong response would describe the initial proposal, the customer and financial evidence gathered, and the alternatives modeled. It should explain how the candidate translated complex findings into an executive-ready recommendation, addressed stakeholder objections, and drove a measurable outcome such as improved conversion, margin, retention, or revenue. The answer should also identify what they would refine in the next pricing decision. Next step ## Apply now. Follow the employer’s application method and review Jobicy’s safety guidance before sharing personal information. Keep exploring ## Related remote jobs. * ![Vonage logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/1bac058d-221.jpg) Vonage Nov 8 New ### [Technical Routing Analyst](https://jobicy.com/jobs/159851-technical-routing-analyst.md) Join Vonage and help us innovate cloud communications for businesses worldwide! 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