Program Manager, Customer Programs

Role Description Dropbox is looking for a Senior Program Manager, Customer Programs to lead complex, cross-functional programs that deepen how we engage, learn from, and deliver value to our customers. This role sits at the intersection of customers, GTM, and Product. You will lead programs that bring customers into important moments across the product and customer lifecycle - from early product learning and customer validation to launches, adoption, advocacy, and strategic customer engagement. You’ll ensure we are engaging the right customers for the right purpose, creating a coordinated experience across Dropbox, and turning what we learn into clear actions for the business. This is a senior individual-contributor role with significant autonomy and executive visibility. You’ll take high-priority initiatives that often span multiple functions, have evolving requirements, or lack an established operating model and turn them into well-run programs. You’ll define the objective, determine the right program approach, align stakeholders, establish ownership and decision points, manage dependencies and risks, and drive execution through measurable outcomes. A critical part of the role is representing the customer experience across the entire program, not simply coordinating internal teams. You’ll think deliberately about who we engage, why we are engaging them, what we are asking of them, how Dropbox shows up across touchpoints, and how we close the loop on their participation. The customer should experience one coordinated Dropbox program even when many internal teams are involved behind the scenes. You’ll work across Sales, Customer Success, Product, Research, Design, Engineering, Product Marketing, Customer Marketing, Analytics, and other teams depending on the program. Over time, you’ll also help Dropbox build more repeatable ways to run customer programs - creating playbooks and operating mechanisms that allow successful approaches to scale without creating unnecessary process. Responsibilities Lead complex customer programs end-to-end, translating ambiguous business priorities into clear objectives, operating plans, milestones, decision points, owners, risks, and measurable outcomes. Create a coordinated customer experience across Dropbox by partnering with Sales, Customer Success, Product, and other teams to ensure customers receive clear expectations, thoughtful engagement, and appropriate follow-through. Lead large cross-functional teams through competing priorities, dependencies, and ambiguity, driving decisions and accountability without relying on formal authority. Connect customer signal to action by ensuring feedback, behavior, and program results reach the right Product and GTM owners and translate into decisions, changes, or clearly documented next steps. Build practical and scalable program infrastructure - including workbacks, decision rights, readiness criteria, status mechanisms, risk/escalation paths, measurement, and reusable playbooks - while avoiding unnecessary process. Provide clear executive-level synthesis of program health, customer signal, risks, tradeoffs, decisions, and recommendations. Requirements 8+ years of experience in program management, customer programs, strategy & operations, GTM operations, product operations, or a related field, with demonstrated ownership of complex cross-functional programs. Demonstrated ability to take a highly ambiguous initiative from problem definition through execution, measurement, and outcome, operating independently with limited direction. Experience leading programs involving customers or customer-facing teams, with strong judgment around customer selection, engagement, communications, expectations, and experience. Demonstrated ability to coordinate multiple senior stakeholders and functions with different priorities, dependencies, and decision rights while maintaining momentum and accountability. Strong operating judgment: able to determine the appropriate level of structure for a problem, make tradeoffs, simplify where possible, and build repeatable mechanisms where needed. Strong written and verbal communication skills, including the ability to synthesize complex qualitative and quantitative information into concise recommendations, decisions, and executive updates. Demonstrated ability to operate as a hands-on senior IC, moving comfortably between strategic problem-solving and the detailed execution required to deliver a program successfully. Preferred Qualifications Experience leading customer programs involving early product feedback, beta/early-access programs, customer validation, product launches, adoption, advocacy, or strategic customer engagement. Experience working across both Product/EPD and GTM organizations and translating customer needs and business requirements between the two. Experience building a new program or operating model and scaling it across products, customer segments, or business priorities. Experience in B2B SaaS, enterprise software, collaboration/productivity technology, or another complex technology environment. Experience using AI and automation to improve program execution, customer insights, synthesis, reporting, or operating efficiency. 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 from our Chief People Officer, Melanie Rosenwasser. Compensation Canada Pay Range $128,400—$173,700 CAD