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Pivoting design strategy mid-build for Chubb's 350K customer claims portal

Overview

I led the design strategy and redesign of the Chubb Benefits consumer claims portal unification initiative, supporting 350K customers, and owned measurement end-to-end, from scaffolding the baseline tracking system to defining delivery success metrics with product owners. Before kickoff, I ran a stakeholder discovery workshop with 10+ insurance agents and led structured validation interviews to refine Chubb Benefits’ existing proto-personas, sharpening our understanding of the end user before design work began.

Entering the build phase, our initial design strategy was constrained to brand updates and targeted, tightly-scoped changes due to the complexity of the backend development requirements. However, midway through delivery the engineering team began a new AI-enabled development strategy without cross-functional alignment, and the entire team — BAs, Product Owners, and QA — had to rapidly adjust.

As the most technical member of the design team, I stepped into a leadership role to own the relationship between design and engineering. I developed a new design strategy highly collaborative with engineering that kept designers as the design authority and expanded the user experience improvements beyond the original targeted updates, all while meeting the delivery timeline.

Role

Lead Experience Designer

Team

Myself, 3 Product Owners, 2 Claims Business Analysts, 1 Technical Business Analyst, 1 Project Manager, 1 Principal Engineer, 1 Testing Lead, 8 Offshore Developers

Tools

Figma, FullStory

Timeline

Nov 2025 – Present

Status

In testing

Password please

Don't have it? Send me an email at knowles.riley@gmail.com, I'd be happy to share.