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 arent 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 andspecifically for this roleInsurance 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 youre 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.

Youll join a close-knit and multidisciplinary UX team working to make cloud software that is at the forefront of the insurance industry. Were 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

• 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 workflowsensuring 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 underwriters 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.

• 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).

• Collaboration: We build on each others 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 $140000 - $210000. 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 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 Guidewires 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 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 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: @GuidewirePandC.

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 its applicable to the position.