Software Engineer – Generative AI and… at Guidewire… · San Mateo

Software Engineer – Generative AI and Documentation Platform Location: United States - San Mateo, CA Summary We’re looking for a Software Developer / Senior Software Developer who is excited about building AI-powered content experiences for developers and technical users. In this role, you’ll work at the intersection of generative AI, search, and technical content. You will use modern web, cloud, and data technologies to help shape how developers and customers discover and use our cloud-based P&C insurance platform through trustworthy, AI-powered content experiences. You will help design, build, and evolve our documentation tooling platform, including our AI chatbot, the MCP server, and content ingestion pipelines. You will also work on the tooling and infrastructure that power our content experiences, and improve content creator workflows and publishing performance. If you’ve built chatbots or search experiences over documentation, APIs, or knowledge bases, you’ll feel right at home in this role. Job Description What you’ll do Work with a team of developers to build and enhance the AI chatbot experience for product documentation, from architecture and prototyping through deployment and iteration. Design, build, and deploy LLM‑powered conversational experiences, including prompt orchestration, tool use, and guardrails. Develop and operate an MCP server and related tooling that securely exposes documentation, metadata, and internal services as tools/functions for LLMs. Integrate AI services with our documentation portal, web applications, and backend systems. Build and maintain ingestion and retrieval pipelines for documentation content (for example, Markdown, DITA, XML, HTML, PDF) to ensure reliable grounding, relevance, and freshness. Integrate AI services with our documentation portal, web applications, and backend systems. Develop and maintain APIs and backend services with attention to performance, reliability, and observability. Design and run evaluation, A/B tests, and telemetry-driven experiments to measure  and improve chatbot and content quality, safety, and user experience. Partner closely with UX and Documentation teams to craft intuitive, trustworthy conversational experiences. Build and enhance tools and automation that improve content creator workflows and publishing performance. Contribute across the stack—frontend, backend, and DevOps—to deliver end‑to‑end solutions, working in a modern CI/CD environment. What you’ll bring Required 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. 3+ years of software engineering experience, including 1+ years working on generative AI systems (such as chatbots, RAG-based search, or LLM-driven applications). Experience with a modern web stack (such as React/TypeScript/ Node.js), modern ML/NLP libraries (such as LangChain), and large-language models (LLMs). Practical experience designing and implementing context-engineering and RAG pipelines, including chunking strategies, embeddings, retrieval, and ranking. Experience working with vector and/or graph databases (such as Pinecone, Weaviate, or Neo4j) to support semantic search, intelligent recommendations, and knowledge-graph–driven experiences. Proven ability to design, build, and operate production services and APIs Comfort working across the full development lifecycle: design, implementation, testing, deployment, monitoring, and ongoing maintenance in a cloud environment. Clear, inclusive communication skills and the ability to collaborate effectively with cross-functional partners. Preferred Bachelor’s or Master’s degree in Computer Science, Engineering, or a related technical field, or equivalent practical experience. Experience with developer/product documentation or other technical content, and an appreciation for information architecture and structured content design. Exposure to XML, Markdown, or structured content models such as DITA. Familiarity with cloud platforms (such as AWS) and deploying scalable, secure services. Experience with observability practices and tools to monitor, troubleshoot, and improve production systems. Background building tools or automation that improve authoring workflows, content quality, site performance, or documentation search and discovery. Your Impact We believe in clarity and setting you up for success. In your first months, you’ll immerse yourself in Guidewire’s platform, documentation ecosystem, and Product Strategy priorities—especially our focus on operational excellence, transformative AI innovation, and customer-centricity. You’ll start by enhancing our existing documentation chatbot, stabilizing ingestion and retrieval pipelines, and collaborating with documentation and UX partners to understand core user journeys. Your work will help developers and customers get fast, accurate answers, accelerate adoption of AI-enabled capabilities like the Agentic AI Platform, and will help improve author efficiency and reduce time-to-market for our content offerings. You will contribute directly to Guidewire’s mission to transform how the world’s P&C insurers do business through secure, cloud-delivered, AI-infused solutions. What’s in it for you The 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 Market-competitive pay and incentive programs Continual development and internal career growth opportunities You’ll also be part of a culture that values inclusive collaboration, access to cutting-edge projects, and leaders who listen and empower you to shape your own growth, aligned with our global Employee Value Proposition pillars of craft, evolve, and belong. As part of our commitment to connection and onboarding, all roles include an in-person orientation experience at one of our offices. By joining this team, you contribute not only to a flagship AI documentation platform, but also to Guidewire’s broader mission to combine digital, core, analytics, and AI to deliver our cloud platform as a service for P&C insurers worldwide. The US base salary range for this full-time position is $113,000 - $169,000 . 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. Disability Accommodations and Guidewire’s Appeals Process. Guidewire provides accommodations to the hiring process to create a fair opportunity for candidates with disabilities to contend for open positions. Accommodation requests should be directed to Accommodations@guidewire.com. If things do not go as hoped, we invite you to use our appeals process. Guidewire promises to independently review any denied accommodation and any decision not to offer you the position. The appeals process is the same in either case. Within five business days of receiving a notice of denial of an accommodation, or receiving a notice of your non-selection for a vacancy, e-mail Accommodations@guidewire.com to make an appeal. Guidewire will assign a new decision-maker to review the request and/or hiring decision, who will then notify you in writing of a decision within 10 business days. 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. Additional Locations: United States - Remote