Senior Site Reliability Engineer

Guidewire; Toronto; On-site; CAD 118,000 - 148,000; Full time

Benefits offered by this job

Health insurance

Dental insurance

Vision insurance

Paid time off

Retirement plan

Annual bonus

Commissions

Long-term incentive plan

Job summary

Guidewire is seeking a Senior Site Reliability Engineer to ensure the reliable operation of our cloud platform and InsuranceSuite products. In this customer-facing role, you will collaborate with customers, partners, and cross-functional teams to understand needs, address concerns, and improve service quality.

You will automate complex systems, contribute to tooling, and drive 24x7x365 availability while maintaining strong customer experience and performance across microservices.

Qualifications

• Bachelor's degree in Computer Science or a related field.
• Experience supporting web applications in live production environments (Java/Apache/Tomcat).
• Solid experience with Bash, Python, and/or Go.
• Strong Linux, AWS and container orchestration knowledge (Docker, Kubernetes/EKS).
• Familiarity with IaC (Terraform/Terragrunt/Terraspace) and devops/gitops tools (Git, Bitbucket, Flux CD, TeamCity).
• Observability experience with Datadog, CloudWatch, PagerDuty.

Responsibilities

• Serve as a technical ambassador, working directly with customers to understand needs and address concerns.
• Collaborate with product development and SRE teams to improve reliability and performance of microservices.
• Automate routine tasks and system maintenance for a multi-tenant SaaS platform.
• Contribute code and strategic ideas to enhance the customer journey and feature delivery.

Skills

Customer-focused communication

Mentorship

Problem solving

Adaptability

Education

Bachelor's degree in Computer Science or related field

Tools

Datadog

CloudWatch

PagerDuty

Terraform

Terragrunt

Terraspace

Git

Bitbucket

Flux CD

TeamCity

Docker

Kubernetes

EKS

Job description

SUMMARY POSITION OVERVIEW

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.

ABOUT THE ROLE

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.

WHAT YOU’LL DO

• Customer-Centric Collaboration: 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.
• Technical Excellence & Reliability: 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.
• Innovation & Automation: 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.
• Cross-Functional Partnership: 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.

WHO YOU ARE

• Technically Proficient: You hold a Bachelor’s Degree in Computer Science or a related field and have solid experience with Bash, Python, and/or Go. You’ve supported web applications in live production environments (Java/Apache/Tomcat) and have a deep understanding of Linux systems, AWS, and container orchestration (Docker, Kubernetes/EKS). You’re experienced with IaC (Terraform/Terragrunt/Terraspace), devops/gitops tools (Git, Bitbucket, Flux CD, TeamCity), and observability platforms (Datadog, CloudWatch, PagerDuty).
• Customer Focused & Communicative: Beyond your technical skills, you’re a strong communicator who can explain complex concepts in a relatable way—both internally and when speaking directly with customers. You’re passionate about mentorship and thrive on teaching and collaborating across teams, always putting the customer’s experience at the forefront. You enjoy engaging with others, have a natural knack for troubleshooting, and are driven by a genuine desire to help customers succeed.
• Driven & Adaptable: You’re a problem solver with a can-do attitude who believes that "if you have to do something more than once, automate it." You adapt quickly to new technologies and processes, ensuring that you can meet the evolving needs of a highly dynamic, customer-centric environment. You’re comfortable with travel (up to 25%) and are eager to interface with customers, partners, and vendors to drive continuous improvement.

JOIN US

If you’re excited by the challenge of ensuring robust, customer-focused operations in a rapidly evolving tech landscape, and you’re as comfortable writing code as you are engaging with clients, then you’ll thrive at Guidewire.

The Canadian CAD base salary range for this full-time position is 118,000.00 - 148,000.00. 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 [e-mail], our disability partner, or schedule a call with an EmployAbility expert (calendar booking slot) for a confidential conversation.

We’re an extraordinary blend of hungry self-starters, intrepid explorers, brainy experts, and loyal allies. Combine all of this, and we make a glorious success story, loaded with down-to-earth, helpful, and passionate people, all on the journey of cloud innovation and best in class technology. Guidewire’s an adventure—and it’s yours for the taking. At Guidewire, we are utterly committed to customer success. We combine digital, core, analytics, and AI to deliver our platform as a cloud service to the P&C Insurance industry. And with the largest R&D team, services team, and partner ecosystem in the industry, we continually evolve and innovate to meet our customers’ needs. We put our values of Integrity, Rationality, and Collegiality first, harboring a culture of honesty and openness that our people never want to lose. And we each bring a little quirkiness—and a little genius to the table. As the landscape of our industry continues to shift, we respond with flexibility and skill. We’re braving uncharted territory, pushing past the conventional with our products, partners, and people.