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.
Job Description
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.
What You'll Bring
- Deep Technical Mastery: 8 to 10+ years of software engineering experience, including SRE or DevOps work, with at least 3+ years in a Staff-level or Technical Lead capacity.
- Cloud Native Expert: Expert-level command of AWS ecosystem and Kubernetes (EKS) orchestration. You should have a proven track record of managing large-scale, distributed cloud environments.
- Automation Specialist: Advanced proficiency in Infrastructure as Code (Terraform/CloudFormation) and configuration management (Ansible/Puppet) within a GitOps framework.
- Software Engineering Acumen: A 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. You are fast, able to build a proof of concept within a week, and fluent with tools such as Claude Code, Cursor, or Copilot. You stay up to date on AI technologies, spec-driven development, and LLM evaluations.
- Design & Architecture Mastery: Highly skilled in software engineering and design principles, comparable to what frameworks such as TOGAF teach (certification is not required). You can own an end-to-end design, write a clear RFC or ADR, and weigh trade-offs honestly.
- Observability Visionary: Deep experience building comprehensive monitoring, SLIs/SLOs, and tracing strategies using tools like Datadog, Prometheus, or Splunk.
- Leadership Mindset: Concrete examples of leadership within operational or software engineering teams, such as taking a project or program from inception to a realized vision. Proven ability to communicate technical risks to stakeholders and collaborate with Product and Engineering managers to align reliability goals with feature delivery.
- Operational Discipline: Experience managing on-call rotations and a "safety-first" mindset. You understand that reliability is the most important feature of any product.
Your Impact
- In your first 90 days: You will build a clear view of where we stand across our global standards, identify "low-hanging fruit" for automation, and establish yourself as a go-to technical resource across the organization.
- In your first 6 months: You will have successfully led a major cross-pod initiative, such as a significant application migration/upgrade, a new observability standard, or a breakthrough in deployment velocity, measurable by a decrease in MTTR and an increase in system uptime.
- Long term: You will shape the future of SRE at Guidewire, influencing our global cloud strategy and building a legacy of engineering excellence that enables our customers to transform the insurance industry.
Location: Mississauga, ON
5050 Satellite Drive, Suite 200
Mississauga, ON Canada L4W 0G1
This is an in-office role. The successful candidate must meet a minimum number of 10 days in the office per month (subject to change).

The Canadian CAD base salary range for this full-time position is 141,000.00 - 176,000.00. Your base pay will depend on your experience, skills, education, training, and location among other factors. All full-time positions or part-time roles working 30 hours or more a week at Guidewire are eligible for benefits that support their health and well-being including health, dental, and vision insurance, paid time off, and a company sponsored retirement plan. In addition, some roles may be eligible for the annual company bonus plan, commissions, and/or long term incentive awards which are contingent on a variety of factors including, but not limited to, company and employee performance.

About Guidewire
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, from new ventures to the largest and most complex in the world, run on Guidewire.
As a partner to our customers, we continually evolve to enable their success. 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.
For more information, please visit www.guidewire.com and follow us on Twitter: @Guidewire_PandC.
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 (calendar booking slot) for a confidential conversation.
