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About the Role

As a Staff Site Reliability Engineer, you will define the technical vision for operating at scale, setting policies, practices, and principles that guide engineers globally, and automating complex processes to deliver a resilient, self-healing cloud ecosystem. This senior leadership role provides deep technical expertise and cross-team architectural influence, advising on future vision and direction to drive the strategic goals of the SRE Application team.

Responsibilities

Serve as a primary technical authority for SRE across the organization.
Own the technical design for strategic deliverables, lead design reviews and strategic engineering decisions.
Act as the final point of escalation for complex technical impediments.
Design and implement systemic improvements to AWS and Kubernetes-based environments.
Lead the creation of frameworks that prevent incidents across the entire organization.
Actively manage complexity so systems stay understandable as they grow.
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.
Champion the transition from manual operations to "Operations as Code."
Lead the development of automated runbooks, self-healing systems, and advanced, consistent CI/CD pipelines (Terraform, GitOps) across the organization.
Steward the centralized tooling engineers rely on to reduce operational friction.
Actively coach and mentor P1-P5 engineers.
Raise the "technical bar" of the team, fostering a culture of curiosity, and ensuring the professional growth of peers through constructive feedback.
Contribute to and help lead the global practice of incident response for the team.
Drive blameless post-mortems culture that goes beyond "human error" to identify deep architectural weaknesses.
Ensure Guidewire learns and hardens its systems after every event.
Proactively identify opportunities to integrate AI/ML and data-driven insights into the observability stack (Datadog/Resolve) to move from reactive monitoring to predictive reliability.
Set the observability standards that teams follow.
Stay current on spec-driven development, LLM evaluations, and modern software engineering tools.
Provide technical oversight for the 24x7 on-call rotation.
Act as a high-level escalation point for complex production incidents, ensuring rapid restoration of service.
Drive the "blameless" culture and post-incident analysis required to eliminate recurring issues.

Requirements

8 to 10+ years of software engineering experience, including SRE or DevOps work.
At least 3+ years in a Staff-level or Technical Lead capacity.
Expert-level command of AWS ecosystem and Kubernetes (EKS) orchestration.
Proven track record of managing large-scale, distributed cloud environments.
Advanced proficiency in Infrastructure as Code (Terraform/CloudFormation) and configuration management (Ansible/Puppet) within a GitOps framework.
Deep software engineering foundation, with the ability to write production-grade code in major languages like Python, Go, C++, C#, or Java with a strong command of object-oriented programming.
Ability to build a proof of concept within a week.
Fluent with tools such as Claude Code, Cursor, or Copilot.
Stay up to date on AI technologies, spec-driven development, and LLM evaluations.
Highly skilled in software engineering and design principles.
Ability to own an end-to-end design, write a clear RFC or ADR, and weigh trade-offs honestly.
Deep experience building comprehensive monitoring, SLIs/SLOs, and tracing strategies using tools like Datadog, Prometheus, or Splunk.
Concrete examples of leadership within operational or software engineering teams.
Ability to take a project or program from inception to a realized vision.
Proven ability to communicate technical risks to stakeholders.
Ability to collaborate with Product and Engineering managers to align reliability goals with feature delivery.
Experience managing on-call rotations.
A "safety-first" mindset.
Understanding that reliability is the most important feature of any product.

Skills

SRE
DevOps
AWS
Kubernetes (EKS)
Infrastructure as Code (Terraform/CloudFormation)
Configuration Management (Ansible/Puppet)
GitOps
Python
Go
C++
C#
Java
Object-Oriented Programming
Claude Code
Cursor
Copilot
AI
ML
Spec-driven development
LLM evaluations
Software engineering design principles
TOGAF
RFC
ADR
Monitoring
SLIs/SLOs
Tracing
Datadog
Prometheus
Splunk
CI/CD pipelines

Location

Mississauga, ON, Canada

Work Type

In-office
Full-time

Experience Level

Staff-level
Technical Lead
8-10+ years software engineering
3+ years Staff/Tech Lead

Salary/Compensations

CAD 141,000.00 - 176,000.00

Benefits

Health insurance
Dental insurance
Vision insurance
Paid time off
Company sponsored retirement plan
Annual company bonus plan (contingent on factors)
Commissions (contingent on factors)
Long term incentive awards (contingent on factors)

About the Company

Guidewire is the platform P&C insurers trust to engage, innovate, and grow efficiently.
We combine digital, core, analytics, and AI to deliver our platform as a cloud service.
More than 540+ insurers in 40 countries run on Guidewire.
We are proud of our unparalleled implementation track record with 1600+ successful projects, supported by the largest R&D team and partner ecosystem in the industry.
Our Marketplace provides hundreds of applications that accelerate integration, localization, and innovation.

Equal Opportunity

Guidewire Software, Inc. is proud to be an equal opportunity and affirmative action employer.
We are committed to an inclusive workplace, and believe that a diversity of perspectives, abilities, and cultures is a key to our success.
Qualified applicants will receive consideration without regard to race, color, ancestry, religion, sex, national origin, citizenship, marital status, age, sexual orientation, gender identity, gender expression, veteran status, or disability.
All offers are contingent upon passing a criminal history and other background checks where it's applicable to the position.
Guidewire is proud to be a disability inclusive employer.
We are committed to providing individualized accommodations and support to candidates for any part of our hiring process.
If you think you may need disability-related accommodations, please email EmployAbility at accommodations-gw@employ-ability.org.uk, our disability partner, or schedule a call with an EmployAbility expert for a confidential conversation.