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Staff Product Manager at Dropbox in Toronto, Ontario | Swiftcruit
Define and execute the product vision, strategy, and roadmap for Stacks and project context experiences within Dropbox.
Clarify the relationship between folders, Stacks, Spaces, projects, Home, AI/chat experiences, and collaborative workflows to create a cohesive user mental model.
Build intelligent project context experiences that bring together Dropbox content, third-party references, comments, tasks, activity, status, versions, and AI-generated summaries in trusted workspaces.
Partner cross-functionally with Engineering, Design, Search, Connectors, Sharing, Platform, and AI teams to deliver scalable and intuitive user experiences.
Define onboarding flows, naming systems, promotion paths, and interaction patterns that help users understand when and why to use Stacks.
Establish product quality bars, experimentation frameworks, learning goals, and success metrics for early design partner programs and broader rollout strategies.
Translate complex technical tradeoffs around retrieval, permissions, freshness, connector reliability, and model behavior into clear product decisions that maintain user trust and simplicity.
Requirements
10+ years of product management experience building and shipping high-impact user-facing products.
Deep experience with conceptual model thinking and a knack for making the complex seem simple.
Strong technical depth with the ability to reason about AI/LLM systems, retrieval quality, search relevance, permissions, platform constraints, and distributed product architectures.
Demonstrated success building products that balance UX simplicity with underlying technical complexity.
Experience working cross-functionally with Engineering, Design, Data Science, AI/ML, and Platform teams to define ambiguous product areas and drive execution.
Strong product instincts around trust, precision, recall, freshness, citations, source boundaries, and human-in-the-loop workflows.
Excellent communication, strategic thinking, and stakeholder management skills with experience influencing senior leadership.
Preferred Qualifications
Experience building AI-powered productivity, search, collaboration, or workspace products.
Familiarity with retrieval systems, connectors, recommendation systems, or context-aware AI experiences.
Experience working on products involving permissions models, shared workspaces, or enterprise collaboration systems.
Strong understanding of modern knowledge work workflows across creative, client-service, media, construction, or project-based teams.
Experience leading 0→1 product initiatives in ambiguous or emerging product categories.
