Senior Software Engineer

Guidewire Software•Toronto, ON

18d•CA$108,000 - CA$135,000•Onsite

About The Position

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 full‑stack expertise across Python, FastAPI, TypeScript, and React to improve observability, streamline customer implementations, and unlock the full value of our AI‑infused 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.

Requirements

Demonstrated ability to embrace AI and apply it to your current role as well as data‑driven 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 hands‑on experience with Python (ideally FastAPI or similar frameworks) and TypeScript/React across both front‑end and back‑end 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 AWS‑based, 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 customer‑focused engineering mindset, with experience partnering closely with implementation, support, or customer success teams and balancing short‑term fixes with long‑term product health.
Clear, concise communication skills and the ability to document runbooks, post‑incident findings, and technical designs for diverse audiences.

Nice To Haves

Experience in enterprise or B2B platforms, ideally in cloud or data‑intensive 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 AI‑driven capabilities.
Familiarity with infrastructure‑as‑code (e.g., Terraform, CloudFormation) and secure coding practices for multi‑tenant 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.

Responsibilities

Lead technical triage for high‑impact, full‑stack 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 AI‑powered features, new product categories, and global market readiness.
Communicate clearly and calmly with both technical and non‑technical stakeholders—inside Guidewire and with customer teams—translating complex technical findings into actionable next steps.