As a Principal Engineer at Dropbox, you will own company critical, loosely defined technical problems with multi year impact, operating at the intersection of technology, product, business strategy, and applied AIYou will define long term technical direction for customer facing experiences used by millions, identifying where AI meaningfully improves customer value and translating evolving business context and industry advances into durable, multi area strategies and roadmaps that shape how Dropbox builds, scales, and innovates, while remaining hands on in software development where it provides the greatest leverageYour influence will span organizations, setting foundational architecture, driving execution standards, and aligning senior technical and product leaders across boundariesYou will lead the responsible introduction and adoption of AI across product capabilities and engineering workflows, bring clarity to the most complex decisions, institutionalize engineering excellence, and contribute directly through critical design, prototyping, and code reviewsIn return, you will operate as a trusted technical partner to senior leadership, shape systems and platforms including AI powered foundations that define Dropbox’s future, and act as a company level technical strategist, advancing Dropbox’s mission to create a more enlightened way of workingOwn and drive technical outcomes across multiple teams and organizations, delivering company critical customer and business impact at scaleDefine long term technical strategy and partner with senior Product and Engineering leaders as the technical owner for the most important company objectivesTackle the most ambiguous and far reaching technical and product problems, shaping what the company builds as much as how it builds itRemain deeply hands on in software development,



owning and implementing the most critical, complex, and foundational parts of the system where leverage is highestInfluence and align roadmaps across organizations, resolving structural bottlenecks and changing how Dropbox builds and operatesArchitect and evolve foundational systems (this may involve both frontend and backend systems) and platforms that enable new product capabilities and operate reliably at the scale of hundreds of millions of usersModel exceptional technical judgment and execution rigor, setting and sustaining high engineering standards across a distributed, virtual environmentDrive AI adoption both to increase productivity and to produce AI based featuresBenefits
On-site fitness and meditation classesCommuter subsidiesMedical, dental, and vision coverageWe offer a generous company contribution toward individual medical, dental, and vision insurance coverage, including contributions toward dependent premiumsStart building a successful 401K retirement plan with our dollar for dollar contribution match, up to $1,500 per quarter to a maximum of $6,000 per calendar yearKeep sharing and collaborating with friends and family even when you’re not at work with free Dropbox space for your whole crewTake the vacation you’ve always dreamed of with up to four consecutive weeks of paid time offCelebrate common holidays without your paycheck taking the hit with 11 company paid holidaysEach Dropboxer has access to 32 hours of paid volunteer time off each year that they can use to support the causes close to their heartsWe regularly offer panels and seminars featuring the best minds in tech, talent, diversity, and beyond that any Dropboxer can attend from the comfort of their homeNo two Dropboxers are the same, and their perks shouldn’t be either. Our Perks allowance empowers employees to customize their benefits in line with what really matters to themAdvanced degree in Computer Science or a related technical field involving substantial software development, or equivalent industry experience demonstrating deep technical mastery Ability to communicate complex technical concepts clearly and persuasively to senior engineering, product, and executive audiences Broad and deep technical expertise across multiple domains, including several of frontend, mobile, search, databases, storage systems, concurrency, and distributed systems Demonstrated success operating at a Principal level, owning company critical technical problems and influencing long term technical direction Strong experience building consumer facing products at scale, with a deep understanding of user experience, performance, reliability, and operational excellence 15+ years of experience designing, building, and evolving large scale software systems with sustained impact across multiple teams or organizations Practical experience applying modern ML, LLM based APIs, and agentic frameworks in production systems, with sound judgment around quality, cost, and risk AI fluency is a core part of how we work and grow. It’s not about being an expert—it’s

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📌 Principal Software Engineer (Winnipeg)
🏢 Dropbox
📍 Winnipeg