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Cloud Computing, Software, Productivity, SaaS

Staff Product Manager, AI Organization Workflows

OnsiteFull TimeStaffCA$196,400–CA$265,700 /yrPosted 2 months ago

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Role summary

Dropbox is seeking a Staff Product Manager to lead AI-driven organization experiences within their core file storage and sharing product. This role involves defining product vision, strategy, and roadmaps, leveraging cutting-edge AI and ML technologies like LLMs and RAG. The Product Manager will deeply understand customer workflows, collaborate with cross-functional teams (Engineering, Design, Data Science, Research, GTM), and ensure scalable, privacy-respecting AI implementations. The position requires strong technical fluency in AI/ML systems, exceptional strategic thinking, and the ability to influence stakeholders at all levels. The ideal candidate has a proven track record of launching complex AI-powered products and a passion for redefining productivity through AI-native experiences.

Role Description

Dropbox is seeking a Staff Product Manager to lead strategy and execution for our next-generation AI led Organization experiences within our Core Product, the file storage and sharing experience (FSS). In this role, you’ll shape the future of how users interact with content and context across tools, using cutting-edge AI to power intuitive, intelligent organization across folders, libraries and living workspaces (called Stacks). You’ll drive vision, define product direction, and partner cross-functionally to deliver transformative features that help users work smarter—not harder.

This is a high-impact, high-visibility, cross-company role that requires a mix of deep customer empathy, strong technical fluency (especially with AI/ML systems), and the ability to navigate and influence across executive and IC audiences. If you're passionate about building AI-native product experiences that redefine productivity, we want to hear from you.

Responsibilities

  • Own and evolve the product vision and roadmap for organization in Dropbox’s core product, setting direction across user experience, core functionality, and backend AI integration.
  • Partner closely with Engineering, Design, Data Science, Research, and GTM to ship innovative features at scale.
  • Translate ambiguous problems and AI opportunities into clear product strategies, experiments, and roadmaps.
  • Deeply understand customer workflows, pain points, and AI needs—through user research, data analysis, and competitive insights.
  • Collaborate with the Dropbox AI/ML and Platform teams to ensure scalable, privacy-respecting, and performant AI implementations.
  • Be a thought leader in the org—coaching other PMs, contributing to product-wide strategy, and influencing AI direction across Dropbox.
  • Define success metrics and deliver measurable impact through rigorous experimentation and iteration.

    • Requirements

  • 10+ years of product management experience.
  • Proven success in building and launching complex, AI-powered products at scale—ideally in productivity, SaaS, or consumer software.
  • Strong technical fluency; you can discuss models, embeddings, and inference with AI engineers and understand constraints/opportunities.
  • Exceptional strategic thinking, with the ability to prioritize among competing opportunities and drive alignment across functions.
  • Experience with LLMs (e.g., GPT, Claude, Gemini), retrieval-augmented generation (RAG), or similar technologies is highly desirable.
  • Excellent communication skills, with the ability to influence at all levels, from ICs to C-level.
  • Passion for the future of work and a deep empathy for Dropbox’s user base.

    • Preferred Qualifications

  • Background in AI/ML, NLP, or data science.
  • Experience working on assistants, chatbots, or productivity-enhancing tools.
  • Familiarity with privacy, security, and ethical considerations in AI product development.

    • Compensation

    Canada Pay Range
    $196,400—$265,700 CAD

    Sample Dropbox interview questions

    • 1

      Propose a system design for serving millions of app downloads concurrently explicitly covering your database architecture and indexing strategy.

      system designmedium
    • 2

      Explain the system design behind computing precise arrival times, factoring in historical traffic patterns and live telemetry data.

      system designmedium
    • 3

      Give me a system design for a massive live event where millions of viewers can watch and answer polls without lagging the stream.

      system designmedium
    • 4

      How would you address the issue of unstructured data in the data warehouse to improve report efficiency for clients?

      system designmedium
    • 5

      Architect a streaming data processing pipeline that can reliably process user viewing metrics in near real-time without losing data during spikes.

      system designmedium

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