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The role involves defining reliability strategies, leading initiatives across teams, enhancing monitoring and incident response, and mentoring engineers at Dropbox.
Role DescriptionResponsibilities
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.
- 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.
- 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.
US Zone 1
This role is not available in Zone 1
US Zone 2
$223,400—$302,200 USD
US Zone 3
$198,600—$268,600 USD
Dropbox Chicago, Illinois, USA Office
Chicago, IL, United States
What you need to know about the Chicago Tech Scene
With vibrant neighborhoods, great food and more affordable housing than either coast, Chicago might be the most liveable major tech hub. It is the birthplace of modern commodities and futures trading, a national hub for logistics and commerce, and home to the American Medical Association and the American Bar Association. This diverse blend of industry influences has helped Chicago emerge as a major player in verticals like fintech, biotechnology, legal tech, e-commerce and logistics technology. It’s also a major hiring center for tech companies on both coasts.
Key Facts About Chicago Tech
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