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 backend expertise across Python, LLM and AI exposure 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.

Document Ingestion & Pipelines: Design and maintain scalable data processing pipelines for ingesting, parsing, cleaning, and indexing multi-format unstructured and semi-structured documents from varied knowledge sources. Architect and optimize Retrieval-Augmented Generation (RAG) pipelines, semantic and hybrid search workflows, and context-assembly engines to deliver accurate, high-relevance information to downstream application models. Build reliable, high-throughput RESTful and streaming APIs in Python to expose context and knowledge services seamlessly to internal and external applications.

Performance & System Efficiency: Optimize background processing, memory overhead, database indexing, caching strategies, and queue-based batch operations to minimize latency and manage operational compute costs. Implement monitoring, logging, and continuous evaluation frameworks to track context retrieval precision,



indexing health, API performance, and data drift in production. Maintain clean abstraction layers across data stores, embedding services, and language models to keep core domain logic modular, decoupled, and vendor-agnostic. 6+ years of experience designing, building, and maintaining production back-end microservices and data pipelines using Python. ~ Hands-on experience with document parsing, text chunking, metadata enrichment, and building scalable pipelines for unstructured knowledge processing. ~ Solid understanding of modern retrieval paradigms, including semantic search, vector indexing, lexical/keyword search, hybrid search, and RAG architectures. ~ Deep familiarity with modern Python back-end practices, asynchronous programming (async/await), relational/non-relational database design, and background job processing systems. ~ Proven experience building clean RESTful/streaming APIs, applying object-oriented/functional design patterns, and maintaining vendor-neutral software abstractions. ~ Experience with cloud environments, containerized deployments (e.g., Docker, Kubernetes), message queues, caching layers, and CI/CD pipelines. ~ Strong commitment to testing, technical documentation, code reviews, and transparent cross-functional collaboration with product, data, and front-end engineering teams.

The Canadian CAD base salary range for this full-time position is 135,000.00 - 169,000.00. 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. Health insurance Dental insurance Company-sponsored retirement plan Annual company bonus plan Long term incentive awards 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. We combine digital, core, analytics, and AI to deliver our platform as a cloud service. 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 and follow us on Twitter: @Guidewire_PandC.

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.

As the landscape of our industry continues to shift, we respond with flexibility and skill.

📌 Entry Level -Software Developer - Web Development (Toronto)
🏢 FHLB Des Moines
📍 Toronto