Turning a complex insurance requirement into a guided onboarding experience

Overview

Renters insurance was a critical part of onboarding, but the experience was fragmented, hard to follow, and not designed for the realities of mobile. Users needed to understand why coverage was required, decide whether to buy a policy or upload their own, and then trust the system to tell them what happened next.

I led the design of a guided onboarding experience that moved users from education to action with clearer decision points, stronger feedback, and patterns built for a new mobile product while still aligning with existing web and property management workflows.

The problem

The previous experience treated insurance like a task to complete instead of a decision that needed context. Important information was either buried, delayed, or disconnected across surfaces.

This created a few core issues:

Goals

This work focused on making the experience easier to understand and easier to complete.

• Help users understand their insurance requirement earlier in onboarding
• Guide users from education to decision to action
• Improve purchase conversion and correct uploads
• Reduce friction during mobile onboarding
• Create reusable patterns for a growing product and design system

Key insight

Users were not just struggling to complete the flow. They were struggling to understand what was required of them before they ever took action.

That shifted the design strategy. Instead of optimizing isolated screens, I focused on building a guided experience that created clarity before users had to make a choice.

Designing the experience

The final experience was structured around a clear progression: understand the requirement, choose a path, complete the task, and receive feedback.

1. Leading with education

I introduced clearer education at the start of the flow so users understood why insurance was required, what counted as valid coverage, and what options were available to them. This helped reduce confusion before they reached the decision point.

Rather than overload people with policy terminology, I focused on plain-language guidance and clear hierarchy.

2. Designing the decision point

One of the most important moments in the experience was the decision between buying a policy and uploading an existing one. I reframed this step so the options felt understandable and intentional instead of abrupt.

This was a critical opportunity to reduce hesitation and prevent users from choosing a path without enough context.

3. Reworking the purchase flow for mobile

As part of the broader mobile launch, I redesigned the purchase experience for a native environment using Material 3 principles and emerging internal patterns. This was not a direct port of the web flow. I restructured layouts, hierarchy, and step transitions to better fit mobile behavior and reduce cognitive load.

The result was a cleaner, more guided path through enrollment.

4. Designing a clearer upload experience

Uploading proof of coverage was one of the highest-friction parts of the experience. I designed a new upload flow with clearer instructions, stronger examples, support for multiple files, and better expectation-setting around what would happen after submission.

This work laid the foundation for better downstream validation and improved submission quality.

5. Integrating real-time results and feedback

Instead of leaving users uncertain after submission, I integrated real-time results where possible and designed clear fallback states when review was still in progress. This helped users understand whether the upload worked, what issues were detected, and what to do next.

I also incorporated lightweight feedback collection to surface confusion points and support future iterations.

6. Contributing to a design system in motion

This project happened while the mobile product and design system were still taking shape. I contributed new component patterns and states that could scale beyond this flow, including upload behaviors, progress states, and interaction patterns that supported consistency across the product.

7. Aligning the full experience across systems

The onboarding flow did not end at the last mobile screen. Outcomes needed to connect to email communications, portal visibility, and property management workflows. I worked to align messaging and expected states across those touchpoints so users were not receiving conflicting signals after taking action.

8. Adapting when product direction changed

Partway through the work, product direction shifted away from a fully mobile live-in experience and back toward deeper integration with the existing web portal. Because the flow had been designed around clear logic and reusable patterns, I was able to adapt the experience without losing the core principles of guidance, clarity, and continuity.

This became one of the strongest lessons from the project: good product design creates structure that can survive platform changes.

Impact

• Insurance conversion increased 28% across onboarding and purchase flow improvements
• Correct uploads increased 17% through better guidance, examples, and feedback
• Drop-off was reduced at key decision points in onboarding
• User understanding improved through clearer reasoning before action

Reflection

This project reinforced that onboarding is not just about getting users through steps. It is about helping them understand what matters, why it matters, and how to move forward confidently.

It also showed the value of designing flexible systems. The strongest parts of the work were not the screens themselves, but the structure underneath them: clear reasoning, intentional decision points, and patterns that could stretch across products and platforms.