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Dropbox

Staff Product Manager

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Remote
Hiring Remotely in Canada
Remote
Hiring Remotely in Canada

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Role Description

As a Staff Product Manager focused on Reclaim.ai within Dropbox, you’ll play a pivotal role in evolving and accelerating the AI-powered scheduling and productivity capabilities of one of Dropbox’s most innovative acquisitions. You will lead product efforts across a wide surface area—from time orchestration, collaboration, and enterprise deployment to exploring adjacent markets that extend Reclaim’s impact. You’ll work directly with Reclaim’s co-founders (now part of Dropbox), while partnering closely with cross-functional leaders in engineering, design, marketing, sales, and support to shape a category-defining product experience.

This is a rare opportunity to operate like a startup PM—owning strategy, execution, and outcomes end-to-end—within the scope, scale, and resources of Dropbox. You’ll get deep exposure to senior leadership, significant latitude to chart your path, and the chance to transform how teams and individuals reclaim their time.

Responsibilities
  • Own and drive the product strategy and roadmap for Reclaim.ai, balancing long-term vision with short-term execution across key areas like AI scheduling, collaboration workflows, and enterprise features.
  • Partner with Reclaim’s co-founders and senior Dropbox leadership to align vision, priorities, and go-to-market strategies.
  • Collaborate deeply with engineering and design to bring features to life—writing specs, defining success metrics, and iterating based on feedback and data.
  • Work cross-functionally with marketing, sales, and support to ensure successful launches, adoption, and customer success across SMB and enterprise.
  • Engage directly with customers and users to deeply understand their needs, pain points, and evolving expectations.
  • Lead and inspire a high-functioning, fast-moving team through ambiguity, change, and rapid growth.
  • Champion a culture of experimentation, urgency, and customer obsession.
Requirements
  • 12+ years of experience in product management or a closely related role, ideally across both early-stage and scaled product environments.
  • Proven track record building and scaling team collaboration, productivity, or scheduling products.
  • Demonstrated ability to work cross-functionally and influence across all levels—especially with senior leadership and executive stakeholders.
  • Experience in fast-paced, ambiguous environments with high ownership and low structure.
  • Strong product intuition with excellent written and verbal communication skills.
  • Comfortable with data—can define metrics, analyze trends, and use insights to inform decisions.
  • Deep empathy for users, especially those managing complex time and coordination workflows.
Preferred Qualifications
  • Experience working on AI-powered products or systems that involve smart automation, decision-making, or time optimization.
  • Familiarity with enterprise deployment models, including top-down SaaS adoption and IT/security needs.
  • Background working within or adjacent to B2B SaaS startups.
  • BA/BS degree in a technical or business discipline.
  • Exposure to design-forward product teams with strong user research practices.
Compensation
Canada Pay Range
$218,500$295,600 CAD

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