Lead UX Designer

Summary Location: San Mateo, CA preferred (2 days per week in office). Open to remote US or Canada 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. Job Description Your Day-to-Day As a UX lead for our AI-Native Underwriting initiatives, you will: 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. What You Need to Be Successful 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). How we work @ Guidewire Collaboration: We build on each other’s ideas and draw on interdisciplinary approaches to craft impactful experiences. Integrity: We stand behind our words and commitments as part of a global community, respecting and recognizing our interdependence. Curiosity: We are lifelong learners, with a growth mentality, who are passionate about advancing our discipline through entertaining new ideas and unique perspectives. Humility: We leverage our expertise while respecting other viewpoints and challenging our own assumptions. The US base salary range for this full-time position is $140,000 - $210,000. 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 View email address on click.appcast.io. 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 View email address on click.appcast.io 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 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. We’re an extraordinary blend of hungry self-starters, intrepid explorers, brainy experts, and loyal allies. Combine all of this, and we make a glorious success story, loaded with down-to-earth, helpful, and passionate people, all on the journey of cloud innovation and best in class technology. Guidewire’s an adventure—and it’s yours for the taking. 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. We put our values of Integrity, Rationality, and Collegiality first, harboring a culture of honesty and openness that our people never want to lose. And we each bring a little quirkiness—and a little genius—to the table. As the landscape of our industry continues to shift, we respond with flexibility and skill. We’re braving uncharted territory, pushing past the conventional with our products, partners, and people.