Context
My Responsibilities
I led the project end-to-end, shaping the design vision, driving discovery workshops, managing scope and stakeholder feedback, mentoring a fellow designer, ensuring high-quality deliverables, and aligning client expectations to lay the foundation for a scalable platform that could expand across Westland’s broader insurance products, with occasional input from my design manager.
Challenge
Strategic Goals
Some data to keep in mind
- 100+ trucking companies in their customer base whose data needs migrating.
- 3000+ truck drivers with active policies.
- Only 3-5 staff members manage all company accounts, drowning in manual and repetitive work.
Discovery Workshop
Approach and Rationale
Given the number of stakeholders and the complexity of the system, it seemed best to bring everyone together and provide a space for questions and alignment. This created an opportunity to turn ambiguity into actionable insights for all: business, design, and implementation teams.
Together with my team, I prepared various exercises and frameworks for alignment during the workshop. I facilitated the majority of the sessions, which were spread out over three meetings lasting two to three hours each.
In the workshops, we:
Defined personas and mapped user journeys.
Mapped user roles, critical tasks, and permissions.
Identified pain points and prioritized key features.
Highlighted technical constraints and challenges of the legacy system.
Outlined a high-level roadmap for immediate and future development, balancing scope and priorities.
Aligned on a North Star and overall project vision.
Snapshots from the Discovery Workshop
Outcome
These workshops clarified priorities, reconciled conflicting requirements, and created a shared vision, enabling a smoother design and implementation process despite legacy system constraints. After synthesizing all findings, we delivered a discovery report to the client outlining the recommended process, timeline, and project scope.
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UX FLow Mapping
Approach and Rationale
Given the legacy system’s complex logic and constraints, we focused on architecture and critical user flows. I led co-creation sessions with core users and collaborated closely with engineers and designers, uncovering key technical limits that shaped our concepts and information architecture.
We broke down complex tasks through iterative sketches and discussions, aligning everyone on a shared vision.
With three user roles, mapping overlapping tasks and permissions proved challenging due to intricate and often unintuitive business rules.
Snapshots of the UX Flow
Outcome
Prioritizing a clear UX flow brought clarity to concept creation and kept features in scope. We revisited it repeatedly throughout the project—not only to guide the design but also to align on future scope and strategically plan the technical architecture and microservices.
Wireframes and Prototyping
Approach and Rationale
Since we worked within complex business logic, we included a dedicated phase for producing wireframes that visualized the new portal in enough detail to validate it with users, stakeholders, and engineers.
We used a wireframe library to quickly assemble reusable components, producing clear wireframes that communicated features and functionality. Each wireframe was annotated with edge cases, business logic, and user role dependencies, reducing ambiguity and ensuring smoother implementation. This approach allowed engineers to begin implementing the architecture without waiting for high-fidelity UI mockups.
Selected Wireframes of the New Insurance Portal
Introducing New Internal Processes That Streamline Collaboration
To streamline the design process and speed time to value even further, I introduced new workflows and a universal design patterns page, giving developers a single source of truth for recurring behaviors like search, filters, and dialogs. This new step was greatly appreciated by our internal developers and significantly reduced their implementation effort.
Outcome
The wireframes were an essential step in solidifying the concept and were especially helpful for sorting out challenges related to the different permission levels. With the low fidelity, we didn’t lose too much time on iterations and improvements after stakeholder and user feedback.
The “universal design patterns page” in Figma that I introduced was reused in other client projects, as it cut down the time for developer handoff and supported the goal of ensuring consistent interactions across the platform.
User Testing
Approach and Rationale
Validation with end users was key for this project. We tested Figma wireframe prototypes to see if users could complete routine tasks more efficiently and identify any points of confusion. Participants were given specific tasks with minimal guidance, allowing us to observe friction and uncover opportunities to improve learnability and usability.
The results showed that we were heading in the right direction: tasks took only half the time to complete—often just a few seconds—and users could quickly locate the features they used daily. Dashboards surfaced essential information more clearly, and feedback was overwhelmingly positive, confirming that we were on the right track.
Snapshot of the User Testing Report
Snapshot from our internal #kudos channel
My manager's slack message sums up the outcome nicely:
UI Delivery
Approach and Rationale
For Phase 1, we delivered high-fidelity mockups and refined the underlying concept based on feedback from end-user testing. Working closely with front- and back-end developers, we simplified and reused patterns across user roles while ensuring datasets could be reliably pulled from the database, respecting data migration constraints.
We extended the design language with custom assets such as context-specific icons, specialized data fields, and interactive components tailored to the trucking insurance context. Every element was crafted to maximize usability, accessibility, and platform-wide consistency, and we collaborated closely with Westland’s internal brand team to ensure full brand compliance.
Selected UI Mockups of the new Insurance Portal
Customer Portal - Driver Enrolment Form
Before (Legacy System) & After (Proposed Solution)
Phase 1 Summary and Client Proposal
Approach and Rationale
Due to the nature of our agency processes, we estimated and pitched the scope for Phases 2 and 3 after closing Phase 1. The artifacts and outcomes from Phase 1 served as the foundation for this work, informing the scope and guiding effort estimations for both the engineering and design teams in the subsequent phases.
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Team & Customer Feedback
Impact
While the project didn’t continue into Phases 2 and 3 due to shifting client priorities, the Phase 1 deliverables set a clear vision for a scalable, user-centered platform.
In just two months, our team delivered a fully design-driven foundation that addressed the legacy system’s biggest pain points—cumbersome workflows, manual processes, limited self-service, and inaccessible data—validated through targeted research and user interviews. We produced high-fidelity mockups and thoroughly documented business logic, edge cases, and intended user behaviors, creating a blueprint that enabled the engineering team to work faster and more efficiently while giving the client a clear path for future growth.
The insights and process improvements from this engagement also informed other TTT internal projects, streamlining workflows, enhancing collaboration, and accelerating design outcomes across the agency.