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Principal Software Engineer, Developer Productivity

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Dropbox

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Location:
Canada

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Category:
IT - Software Development

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Contract Type:
Not provided

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Salary:

244000.00 - 330100.00 CAD / Year
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Job Description:

Dropbox is seeking a Principal Engineer to define the long-term technical vision and execution strategy for Developer Productivity. This role will serve as the architectural and strategic leader for building a modern, AI-augmented internal developer experience platform serving Dropbox engineers across our multi-product stack. In this high-impact, cross-cutting role, you’ll shape how development flows from idea to production—streamlining workflows, reducing friction, and introducing agentic workflows that enable faster, higher-quality software delivery. You’ll work across distributed systems, address the challenges of a complex monorepo, and introduce intelligent systems that empower developers through automation, guidance, and seamless tooling integration. This is a career-defining opportunity to reimagine how software gets built at scale—and bring the promise of AI to everyday developer tasks.

Job Responsibility:

  • Define the long-term architecture for Dropbox’s developer productivity platform, including a unified internal developer portal (“Dropbox Console”), default workflows, and intelligent agents
  • Own platform-wide architectural patterns that streamline the entire SDLC: from local dev and CI to testing, debugging, and deployment
  • Build abstractions and systems that scale across monorepo, multi-platform (desktop/web/mobile), and hybrid cloud/on-prem environments
  • Lead the design and implementation of agentic workflows for core developer tasks—code reviews, test generation, flaky test triage, documentation, migrations, etc
  • Design systems that embed safe and assistive AI directly into development surfaces and tools, enabling faster iteration while preserving quality and auditability
  • Define best practices for integrating LLMs into engineering workflows, including supervision checkpoints, rollback strategies, and metrics
  • Partner with infrastructure, product, and engineering teams to identify bottlenecks and define metrics that matter for business outcomes
  • Drive migration from fragmented tools and tribal workflows to a unified platform that enables flow-state for developers
  • Set and enforce standards for quality, safety, and reliability of automation and AI workflows
  • Serve as a technical multiplier, mentoring teams across Dropbox and raising the bar on system design, platform thinking, and developer empathy
  • Collaborate deeply with PMs, DX researchers, SREs, and leadership to align priorities and deliver developer delight
  • Represent Dropbox in the external platform and AI productivity communities through talks, papers, and open-source contributions where appropriate

Requirements:

  • 12+ years of engineering experience with a deep background in distributed systems, internal developer platforms, or DevProd infrastructure
  • Deep understanding of monorepos, complex CI/CD setups, local development, multi-platform development, and developer journey mapping
  • Demonstrated experience building large-scale platforms with high reliability, composability, and extensibility
  • Passionate about AI, with hands-on experience (or deep exposure) to integrating LLMs, RAG systems, or intelligent assistants into engineering workflows
  • Strong product sense and empathy for developer pain—capable of translating data and feedback into high-leverage solutions

Nice to have:

  • Experience leading or contributing to AI developer tooling, or developer experience
  • Proven success operating as a principal+ level engineer across large orgs
What we offer:
  • Competitive medical, dental and vision coverage
  • Retirement savings through a defined contribution pension or savings plan
  • Flexible PTO/Paid Time Off, paid holidays, Volunteer Time Off, and more
  • Income Protection Plans: Life and disability insurance
  • Business Travel Protection: Travel medical and accident insurance
  • Perks Allowance to be used on what matters most to you
  • Parental benefits including: Parental Leave, Fertility Benefits, Adoptions and Surrogacy support, and Lactation support
  • Mental health and wellness benefits

Additional Information:

Job Posted:
December 31, 2025

Employment Type:
Fulltime
Work Type:
Remote work
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