After receiving feedback from our Director of Product on the initial mockups for skipping carriers, we tackled a new challenge: enabling users to jump between carrier question sets, whether completed or not. The main challenge was determining how carriers would appear in the Real-time eligibility panel panel (RTE) and how to display their statuses. Once users reach the carrier question sets, all carriers in the Real-time eligibility panel panel (RTE) become unlocked. We needed to clearly communicate this flexibility to end users.Through several rounds of design iterations and feedback, I tested various combinations of iconography, verbiage, and status indicators for carrier elements within the Real-time eligibility panel panel (RTE). After multiple team reviews, we began to reach consensus on the preferred design concepts.

Building on the wireframe concepts, our initial designs focused on the user journey from Quote Presentation through quote selection and checkout. Key discussions centered on two main questions: whether to include a shopping cart feature in version one of Bind & pay, and whether to create dedicated product detail pages for quotes beyond the existing tab view. We conducted extensive comparisons with traditional commercial insurance experiences, and the design phase extended several weeks as we incorporated various stakeholder feedback.

After making design progress on the functionality of skipping and jumping between carriers, our next challenge was handling multiple insurance products from a single carrier. Within the Bold Penguin Terminal, agents choose which coverage types to include in their application. As they proceed to the carrier question sets, one carrier might offer multiple coverage types. For example, if Jane Smith wants General Liability and Workers' Compensation for her florist shop, a single carrier like Chubb might offer quotes for both types after she completes their question set.

The design challenge was deciding how to display multiple coverage types from one carrier in the Real-time eligibility panel panel (RTE). Should we show Chubb's General Liability and Workers' Compensation quotes in the same card or separate cards? While the decision was straightforward—multiple cards would take up too much vertical space—executing it elegantly was complex. Through trial and error and valuable team feedback, we created a clean, user-friendly solution that displayed multiple coverage types within a single carrier card.

We also explored using a bottom sheet card to display estimated annual premiums and price ranges for selected coverage types. While leadership liked this concept, we ultimately chose a different approach for showing pricing information.

As our design effort progressed, we decided to put the shopping cart feature on hold and allow users to purchase only one policy at a time. The happy path user flow emerged with these steps: Quote Presentation page, a detailed Product Page for final application edits, and Checkout for selecting payment plans and completing legal acknowledgments. During a feedback meeting, stakeholders informed us that payment information would not be collected within the Terminal. Instead, we would overlay an iframe on top of the checkout experience, allowing users to enter payment details on the carrier's portal. After payment processing, users would see a policy bound page displaying their policy number, agent contact information, and downloadable policy documents.Through subsequent meetings, I discovered that carriers with the Bind & pay feature would implement different checkout payment experiences. Homesite would use an iframe overlay for payment information, Markel would redirect to their carrier portal for payment collection, and Hiscox would offer an iframe with direct bill options for customer invoicing. We uncovered these details during feedback sessions with our carrier partners, gaining deeper insight into their payment collection processes. This meant our Bind & pay happy path would now include three distinct variations based on the carrier.

After making significant design progress, my next task was to create a clickable prototype showing the ideal user journey. We planned to present this prototype to our target customers in user interviews to gather insights about their understanding of the new features and their expectations.

During a recent customer feedback session with InsureCherokee, we gained valuable insights about the product. The participant, an experienced user, praised the ability to skip to competitive carriers and the design's simplicity. They also suggested additional features to enhance the product's usability for their specific needs. Here are the key takeaways from the discussion.

• The participant found the ability to skip non-competitive carriers highly beneficial, allowing him to focus on carriers that are known to be competitive for specific classes.
• The panel design, particularly before and during carrier question sets, was well-received.
• Grouping by carrier and presenting estimated premiums were highlighted as useful features, providing clarity and actionable information.
• The ability to skip to carrier-specific question sets and bind directly without completing other steps was seen as a significant efficiency booster.
• The participant emphasized that endorsements are critical for contractor policies, suggesting the inclusion of endorsements to showcase the full offering.
• When asked for any dislikes or areas for improvement, the participant stated there was nothing he disliked, reinforcing the product’s helpfulness and usability.

The feedback session with InsureCherokee affirmed the product's potential to streamline workflows and deliver competitive advantages. We conducted six customer feedback sessions in total, and I participated in five of them.

After syncing with our product manager about the carriers' different payment collection methods, I revised the designs to show the user flows for Homesite, Markel, and Hiscox. I fine-tuned these designs and created prototypes to demonstrate the experience to agents. During the customer feedback session with several agents, our product manager led the discussion while I took notes, which I later reviewed to identify common patterns.After gathering customer feedback, we uncovered several key insights that raised important questions:

• How would we handle additional interests on commercial insurance applications?
• How should we manage payment failures on third-party pages?
• How could we deliver policy documents for carriers without API support?

Additionally, we faced technical complexities around application editing during the checkout process. We needed to decide whether to implement this in a modal or full-screen page, and determine which application sections users could edit. While we had made significant progress with the overall design of Bind & pay, this feedback highlighted the need to prioritize features carefully for the initial launch.

In our final round of designs, my challenge was to showcase the entire application process with our revamped Real-time eligibility panel panel (RTE). This included demonstrating various scenarios: completing carrier applications and receiving quotes, handling error responses, skipping certain carriers, leaving some incomplete, and finally reaching the quote presentation page. The final layer of complexity involved showing how users could return to the application to complete remaining carrier questionnaires and see their quotes update accordingly. While this was a complex process with numerous design challenges, our team collaborated effectively to bring it across the finish line. We held two refinement meetings with our development teams to address edge cases and distribute the workload. Overall, this has been one of the most enjoyable projects I've worked on at Bold Penguin.

Several weeks into the Bind & pay design process, we reached an inflection point where I was asked to hand off the Checkout designs to our Lead Product Designer while I pivoted to focus on Quote Presentation designs. As a team player, I accepted this decision, but after returning from a week-long vacation, I discovered our lead designer had significantly altered many of my Checkout design concepts. While this was humbling for someone who takes pride in their work, I set aside my ego and had a professional conversation with our lead designer about the importance of design consistency across our efforts. I saw this as an opportunity to establish a more theoretical vision for our design system and its guidelines. He agreed, and together we worked toward creating and documenting a unified solution within our design system.