Lead UX Designer

Guidewire Software•San Mateo, CA

1d•$140,000 - $210,000•Hybrid

About The Position

Join Guidewire Design! What does the future of insurance look like when AI, Machine Learning, and Automation aren’t just add-ons, but the core foundation of the user experience? At Guidewire, we are actively redefining how enterprise insurance software operates and reinventing the day-to-day reality for Agents, Adjusters, and—specifically for this role—Insurance Underwriters. We are tackling a massive, complex question: "How might we leverage AI-native experiences to synthesize massive data, surface hidden risks, and guide underwriters toward faster, smarter decisions?" If you’re a heavy-hitting UX lead who loves transforming high-density data and complex AI workflows into elegant, intuitive, and trustworthy human-centered experiences, we want you on this journey. You’ll join a close-knit and multidisciplinary UX team working to make cloud software that is at the forefront of the insurance industry. We’re committed to an inclusive workspace that embraces people with diverse backgrounds, experiences, skills, and talents. At Guidewire, we foster a culture of curiosity, innovation, and responsible use of AI — empowering our teams to continuously leverage emerging technologies and data-driven insights to enhance productivity and outcomes.

Requirements

4-7 years of UX design experience, with a significant portion dedicated to complex SaaS platforms, big data products, or AI/ML-driven applications.
A proven track record in Risk Management environments (FinTech, InsureTech).
Fluency in AI/ML UX: Clear understanding of the nuances designing for probabilistic systems rather than deterministic ones (e.g., handling AI errors, feedback loops, prompt interfaces, and data confidence intervals). Deep systems thinking is a must.
Excellent Storytelling Skills: Able to balance emotional, user-centered, and data-driven storytelling to drive decisive action.
Workshop Facilitation & Leadership: Proven experience running design-thinking workshops that align cross-functional teams around a unified user problem.
Research Capability: Direct experience in planning, executing, and synthesizing both qualitative and quantitative research.
Comfort and fluency using AI tools: Adept at using AI tools in your daily work (e.g. NotebookLM, Gemini, Claude Code)
An Exceptional Portfolio: A body of work demonstrating a rigorous human-centered design process, mastery of complex technical domains, and measurable business impact. (Online or shareable PDF).

Responsibilities

Pioneer the AI-Native Vision: Establish a UX vision for underwriting solutions that leverage Generative AI, LLMs, and agentic workflows. Socialize and champion this vision with stakeholders across the organization.
Design for Trust & Explainability: Design "human-in-the-loop" experiences, including patterns that clearly explain AI-generated insights , confidence levels, and recommendations that are aligned to our AI user experience research and design principles.
Shift from Reactive to Proactive Workflows: Help evolve the underwriting process from manual data assembly to exception-based, automated workflows—ensuring high-value broker requests are triaged and processed with unprecedented speed.
Tame Multi-Modal Data: Create elegant interfaces that seamlessly synthesize structured and unstructured risk data into actionable narratives.
Architect Decision-Support Systems: Design interfaces that embed intelligent recommendations directly into the underwriter's natural workflow without causing cognitive overload.
Collaborate with Cross-Functional Teams: Partner closely with Product Management, Data Science, and Engineering to align technical feasibility with user desirability, ensuring our data models serve human needs.
Align vision with product roadmaps: Ability to create product designs along product roadmap and drive toward long-term vision through close collaboration with Product and Engineering. Be flexible to adjust design approaches into “Now-Next-Future” versions.