Turning a complex insurance requirement into a guided onboarding experience

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

Overview

Renters insurance was a critical part of the move-in process for both renters and property managers. However, 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 came 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. Helping users understand and choose

The first step of the experience needed to do two things at once: help users understand their insurance requirement and guide them toward the right path.

I combined education and decision-making into a single, intentional moment where users could clearly see why coverage was required, what counted as valid, and what options were available to them — whether purchasing a policy or uploading their own. This reduced confusion early and helped users move forward with more confidence instead of hesitation..

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

2. 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.

3. 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.

4. 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.

5. 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.

6. 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.

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.