Dropbox is a Virtual First company. For this role, we are currently only authorized to hire candidates from the following provinces: Alberta, British Columbia, Ontario, and Saskatchewan.

Role Description

As a Site Reliability Engineer focused on company-wide reliability strategy, you will play a crucial role in advancing Dropbox’s stability, observability, incident response, and operational excellence as AI technologies reshape how software is built and operated. You will help define the reliability strategy for a new chapter of agentic development and AI-enabled software delivery, including preparing Dropbox for increases in pull request volume, service complexity, incident patterns, and demand for debugging and monitoring tools. You will partner across Engineering, Product, and leadership teams to raise the bar for reliability, guide long-term platform investments, and ensure Dropbox continues to deliver dependable experiences for millions of users.

Our Engineering Career Framework is viewable by anyone outside the company and describes what’s expected for our engineers at each of our career levels. Check out our blog post on this topic and more here.

Responsibilities

• Define and evolve Dropbox’s company-wide technical reliability strategy to support the changing engineering environment created by AI-assisted and agentic software development.
• Set multi-year reliability goals, standards, and roadmaps across observability, debugging, incident management, service health, and operational readiness.
• Lead cross-team initiatives that reduce reliability risk as software delivery velocity, pull request volume, service complexity, and incident volume increase.
• Partner with engineering leaders and platform teams to improve monitoring, alerting, debugging, SLOs, SLAs, and incident response systems at company scale.
• Identify emerging reliability risks introduced by AI-enabled development workflows and design scalable systems, processes, and guardrails to mitigate them.
• Provide technical leadership and mentorship to engineers across teams, raising engineering quality, reliability judgment, and operational excellence.
• Drive clear communication and alignment with senior stakeholders on reliability priorities, tradeoffs, risks, and execution progress.

Many teams at Dropbox run Services with on-call rotations, which entails being available for calls during both core and non-core business hours. If a team has an on-call rotation, all engineers on the team are expected to participate in the rotation as part of their employment. Applicants are encouraged to ask for more details of the rotations to which the applicant is applying.

Requirements

• BS degree in Computer Science or related technical field involving coding (e.g., physics or mathematics), or equivalent technical experience.
• 12+ years of experience in software engineering, site reliability engineering, infrastructure engineering, or related technical roles.
• Proven ability to define and deliver multi-year, multi-team reliability, infrastructure, or platform strategies with measurable business and customer impact.
• Deep experience with distributed systems, production operations, observability, incident response, SLOs/SLAs, debugging, and reliability risk management.
• Demonstrated ability to diagnose complex technical problems, debug production systems, automate operational workflows, and design resilient software components.
• Experience influencing engineering roadmaps across multiple teams and making technical decisions that optimize for the broader engineering organization.
• Strong communication and collaboration skills, with the ability to align cross-functional stakeholders through ambiguity and drive execution across teams.

Preferred Qualifications

• Experience adapting reliability strategies, developer tooling, or operational processes for AI-assisted software development workflows.
• Experience building or scaling observability, debugging, incident management, or developer productivity platforms for large engineering organizations.
• Experience leading reliability improvements in environments with high deployment velocity, complex service dependencies, and large-scale production systems.
• Track record of mentoring senior engineers, setting technical standards, and spreading reliability best practices through documentation, reviews, talks, or architecture guidance.
• Familiarity with AI-enabled tooling, agentic development workflows, or operational risks introduced by rapid automation in the software development lifecycle.

Compensation

Canada Pay Range

$204,900—$277,200 CAD

Company Description

Dropbox isn’t just a workplace—it’s a living lab for designing a more enlightened way of working. We’re a global community of bold visionaries and resourceful doers shaping the future of Dropbox and, in turn, the future of work. Our Virtual First model combines the autonomy of a distributed workplace with the power of human connection, creating space for meaningful work and lasting relationships. With a startup mindset and enterprise-level opportunities, we expect Dropbox employees to think critically, stay curious, and use modern tools, including AI, to improve how work gets done. Here, you can be who you are and grow into who you’re meant to be. You own your impact, helping make work more intuitive, joyful, and human for yourself and hundreds of millions of people worldwide. If you’re ready to push boundaries and challenge yourself, Dropbox is ready for you.

Team Description

The Dropbox Engineering Team develops the technology, platforms, and products that create more enlightened ways of working for hundreds of millions of people. Customers rely on Dropbox to manage, share, and collaborate on content seamlessly—our engineering makes that easier and more intuitive than ever before.Our platform features a robust systems software layer that stores and processes exabytes of data, and a suite of growing services that enhance core products like our sharing and sync engine. We’re also driving innovation with new offerings such as Dash, our AI-powered knowledge management engine. Our infrastructure spans high-performance servers and cutting-edge components across multiple data centers worldwide, ensuring reliability, speed, and scalability at a global scale. We think like a startup but build for an enterprise, exploring new possibilities that transform how people work. If you're excited about turning complex technical challenges into intuitive solutions at scale, join our Engineering team.

Virtual First

Dropbox’s Virtual First way of working is designed to help people do their best work with flexibility, autonomy, and connection. Day to day, teams work remotely with nonlinear schedules and core collaboration hours that support deep focus and individual working styles. We prioritize asynchronous communication to improve clarity, respect deep work time, and reduce unnecessary meetings. While remote work is the primary experience for our employees, we also prioritize intentional, in-person connection. We bring teams together through regular team gatherings, on-demand workspaces, and Dropbox Neighborhood events in order to strengthen team cohesion, foster creativity, and enhance momentum. Virtual First is built to provide the same access to opportunity, growth, and impact for everyone, regardless of location.

This role requires travel to offsites and various other team gatherings (approximately 5-10% of the year or 2-3 days per quarter). We provide advance notice when possible and encourage candidates to discuss any accommodation needs during the interview process.

Dropbox supports responsible use of AI for preparation, but misrepresentation of skills or experience is not permitted. See our AI Principles.

Dropbox is an equal opportunity employer. We are a welcoming place for everyone, and we do our best to make sure all people feel supported and connected at work.