Staff Site Reliability Engineer, Application

Location: Canada - Toronto

Summary

Join Guidewire's Product Development & Operations (PDO) organization as a cornerstone of our Site Reliability Engineering team. We are the architects of stability for the Guidewire Cloud Platform, ensuring the world's leading P&C insurers can depend on our mission-critical applications. As a Staff Site Reliability Engineer, you aren't just maintaining systems; you are defining the technical vision for how we operate at scale, setting the policies, practices, and principles that guide our engineers around the world, and automating the complex to deliver a resilient, self-healing cloud ecosystem.

The Role

This is a senior leadership role with global reach. You will act as a Staff Site Reliability Engineer (P5), providing deep technical expertise and cross-team architectural influence, reporting directly to the Senior Director of Site Reliability Engineering for Applications. You will advise on future vision and direction and help drive the strategic goals and projects of the SRE Application team. You will bridge the gap between long-term reliability strategy and day-to-day execution, ensuring that our applications are not only stable but also evolving through elite software engineering practices.

Few engineers get to decide how reliability works for an entire global organization. This role puts the standards, the designs, and the direction in your hands.

What You'll Do

Technical Leadership: Serve as a primary technical authority for SRE across the organization. You will own the technical design for strategic deliverables, lead design reviews and strategic engineering decisions, and act as the final point of escalation for complex technical impediments.

Architectural Influence: Design and implement systemic improvements to our AWS and Kubernetes-based environments. You won't just fix incidents; you will lead the creation of frameworks that prevent them across the entire organization, and you will actively manage complexity so our systems stay understandable as they grow.

Drive Engineering Excellence: Set and drive global standards for automated unit and integration test coverage. Lead by example through hands-on coding (AI, Python, Go, or Java), rigorous code reviews, and the promotion of "Clean Code" and testing standards. Prototype quickly, taking an idea to a working proof of concept in days.

Toil Elimination & Automation: Champion the transition from manual operations to "Operations as Code." You will lead the development of automated runbooks, self-healing systems, and advanced, consistent CI/CD pipelines (Terraform, GitOps) across the organization, and steward the centralized tooling our engineers rely on to reduce operational friction.

Mentorship & Growth: Actively coach and mentor P1-P5 engineers. You are responsible for raising the "technical bar" of the team, fostering a culture of curiosity, and ensuring the professional growth of your peers through constructive feedback.

Incident Management & Post-mortems: Contribute to and help lead the global practice of incident response for the team. You will drive our blameless post-mortems culture that goes beyond "human error" to identify deep architectural weaknesses, ensuring Guidewire learns and hardens its systems after every event.

AI & Innovation: Proactively identify opportunities to integrate AI/ML and data-driven insights into our observability stack (Datadog/Resolve) to move from reactive monitoring to predictive reliability, and set the observability standards that teams follow. Stay current on spec-driven development, LLM evaluations, and the modern tools of software engineering.

Production Stewardship & On-Call Excellence: Provide technical oversight for our 24x7 on-call rotation. As a P5 Staff SRE, you will act as a high-level escalation point for complex production incidents, ensuring rapid restoration of service while driving the "blameless" culture and post-incident analysis required to eliminate recurring issues.