Insurance Software Jobs in Toronto, ON (NOW HIRING)

Summary

Our Product Strategy organization is shaping the next generation of Guidewire's cloud, data, and AI-powered platform for P&C insurers worldwide. We partner closely with Product Development & Operations to deliver secure, scalable solutions that improve reliability, performance, and customer value. You'll join a collaborative, inclusive team that experiments, learns by doing, and works across Python, TypeScript/React, and modern AWS-native services.
In this Senior Software Engineer role, you'll be the engineering front line for complex customer scenarios-triaging production issues, engineering hotfixes, and building the tools that keep our platform reliable at scale. You'll apply deep SaaS fullstack expertise across Python, FastAPI, TypeScript, and React to improve observability, streamline customer implementations, and unlock the full value of our AIinfused product strategy. This is an opportunity to contribute directly to Guidewire's mission to transform how the world's P&C insurers do business through cloud, analytics, and AI, while shaping how our platform runs in real customer environments every day.

Job Description

What you'll do

• Lead technical triage for highimpact, fullstack production issues: investigate logs, traces, API calls, and database behavior to identify root causes quickly and implement safe, targeted hotfixes and patches.

• Partner with implementation, Product, and customer success teams to unblock complex customer rollouts-designing and implementing configuration changes, REST API integrations, and data flows that align with our Product Strategy priorities around AI, cloud, and data platform adoption.

• Design, build, and maintain internal tools, admin utilities, CLI scripts, and workflow automations that reduce implementation effort and time, and help teams achieve our goals for operational excellence and measurable customer value.

• Expand platform observability by enhancing dashboards, alerts, and runbooks using tools like Datadog, Sentry, and CloudWatch, helping us detect and resolve issues before they affect customers and supporting our reliability and gross margin targets.

• Improve and harden our CI/CD and deployment pipelines to support secure, scalable, and efficient operations that align with Product Strategy's focus on operational excellence and cloud readiness.

• Collaborate with core engineering to turn recurring field issues and customer feedback into prioritized backlog items, influencing roadmap decisions around AIpowered features, new product categories, and global market readiness.

• Communicate clearly and calmly with both technical and nontechnical stakeholders-inside Guidewire and with customer teams-translating complex technical findings into actionable next steps.

• At Guidewire, we foster a culture of curiosity, innovation, and responsible use of AI-empowering our teams to continuously leverage emerging technologies and datadriven insights to enhance productivity and outcomes.

What you'll bringRequired

• Demonstrated ability to embrace AI and apply it to your current role as well as datadriven insights to drive innovation, productivity, and continuous improvement.

• 6+ years of experience building, maintaining, or supporting SaaS or enterprise web applications in production environments.

• Strong handson experience with Python (ideally FastAPI or similar frameworks) and TypeScript/React across both frontend and backend services.

• Proven diagnostic skills: comfortable tracing distributed requests, analyzing logs and metrics, profiling performance, and debugging complex production issues under time pressure.

• Experience working in AWSbased, containerized environments (e.g., ECS, EKS, Docker), with practical familiarity with observability tooling such as Datadog, Sentry, or CloudWatch.

• Demonstrated experience building REST API integrations, CLI tools, admin portals, or workflow automations to solve operational or customer onboarding challenges.

• A customerfocused engineering mindset, with experience partnering closely with implementation, support, or customer success teams and balancing shortterm fixes with longterm product health.

• Clear, concise communication skills and the ability to document runbooks, postincident findings, and technical designs for diverse audiences.

Preferred

• Experience in enterprise or B2B platforms, ideally in cloud or dataintensive domains; exposure to insurance or financial services is a plus.

• Background working on or alongside product/platform strategy, SRE, or platform engineering teams focused on reliability, scalability, or AIdriven capabilities.

• Familiarity with infrastructureascode (e.g., Terraform, CloudFormation) and secure coding practices for multitenant SaaS.

• Experience contributing to roadmap discussions or influencing product direction based on production and customer insights.

• Bachelor's degree in Computer Science, Engineering, or a related field, or equivalent practical experience.

Your Impact

We believe in clarity and setting you up for success. In your first months, you'll learn our platform, observability stack, and Product Strategy priorities around AI, cloud, and data, then take ownership of triaging complex production issues and leading technical resolution for key customer scenarios.

As you progress, you'll build and evolve internal tools, automations, and observability that shorten implementation timelines, reduce incident frequency, and improve timetorecovery-directly contributing to our goals of operational excellence, transformative innovation, and customercentricity in how insurers run on Guidewire.

Over time, your insights from the field will shape product decisions, influence how we bring new AIdriven capabilities to market, and help Guidewire continuously transform how the world's P&C insurers do business through our cloud platform, analytics, and AI.

What's in it for youThe people we employ give their all, and in return, we offer flexibility wherever we can, such as:

• Flexible work environment

• Health and wellness benefits

• Paid time off programs including volunteer time off

• Marketcompetitive pay and incentive programs

• Continual development and internal career growth opportunities

Guidewire also embraces a culture of inperson interviews for all applicants and onsite orientation for all new hires, so you can build strong relationships from day one and fully experience our inclusive, collaborative culture.

The Canadian CAD base salary range for this full-time position is 108,000.00 - 135,000.00. 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.