Senior Site Reliability Engineer

Guidewire Software•Toronto, ON

About The Position

At Guidewire, we make software that offers Property and Casualty (P&C) Insurance companies the tools to take care of their customers when they need it the most, whether that’s a time of crisis, a natural disaster, an accident, or exposure to cyber risks. We build the core applications that insurance companies use to sell and underwrite policies, settle claims, and bill their customers. We also have a portfolio of innovative products serving the needs of P&C insurance companies in areas such as data management, digital online portals, and predictive analytics. We run these products on the Guidewire Cloud Platform, and we help hundreds of insurance providers all over the world to handle billions of dollars of business. We are proud to be voted a Top Cloud Employer on Glassdoor by our own employees and positioned as a market leader by industry experts like Gartner. We have a fun work environment and a culture that lives by our core values of integrity, rationality, and collegiality. At Guidewire, we believe that great technology is powered by great people. We’re searching for a Senior Site Reliability Engineer who not only brings deep technical expertise but also thrives on engaging with customers, partners, and cross-functional teams. In this customer-facing role, you will ensure the smooth, reliable operation of our flagship cloud platform and InsuranceSuite products—all while championing a customer-first mindset. If you’re passionate about automating complex systems and equally enthusiastic about building genuine human connections, we want to hear from you.

Requirements

Bachelor’s Degree in Computer Science or a related field
Solid experience with Bash, Python, and/or Go
Supported web applications in live production environments (Java/Apache/Tomcat)
Deep understanding of Linux systems, AWS, and container orchestration (Docker, Kubernetes/EKS)
Experienced with IaC (Terraform/Terragrunt/Terraspace)
Experienced with devops/gitops tools (Git, Bitbucket, Flux CD, TeamCity)
Experienced with observability platforms (Datadog, CloudWatch, PagerDuty)
Strong communicator who can explain complex concepts in a relatable way—both internally and when speaking directly with customers.
Passionate about mentorship and thrive on teaching and collaborating across teams, always putting the customer’s experience at the forefront.
Enjoy engaging with others, have a natural knack for troubleshooting, and are driven by a genuine desire to help customers succeed.
Problem solver with a can-do attitude who believes that “if you have to do something more than once, automate it.”
Adapt quickly to new technologies and processes, ensuring that you can meet the evolving needs of a highly dynamic, customer-centric environment.
Comfortable with travel (up to 25%) and are eager to interface with customers, partners, and vendors to drive continuous improvement.

Responsibilities

Serve as a technical ambassador, working directly with customers to understand their needs, address concerns, and ensure our systems support their business goals.
Participate in design reviews, production readiness checks, and post-incident analyses with both internal teams and customers to continuously improve service quality.
Collaborate closely with product development and other SRE teams to enhance the reliability, performance, and efficiency of our microservices applications.
Analyze data from observability and monitoring tools to optimize operational metrics across our customer-focused systems.
Develop, document, and share technical solutions and training materials to empower your colleagues and ensure consistent, high-quality support.
Lead efforts to automate routine tasks and system maintenance on our SaaS multi-tenant infrastructure, ensuring 24x7x365 operations that meet both technical and customer experience benchmarks.
Create and refine tooling and processes that improve incident management, driving proactive measures to prevent issues before they affect our customers.
Work alongside diverse teams—engineering, product development, and support—to integrate new features seamlessly and maintain an open dialogue about customer feedback.
Contribute code and strategic ideas that not only solve technical challenges but also enhance the overall customer journey.