Marcus White - Senior Product Designer Portfolio

Context

Bold Penguin is an insurtech company that has a suite of products helping commercial insurance agencies quote and buy policies efficiently and accurately for their clients.Bold Penguin's flagship product is the Bold Penguin Terminal, which allows agents to get multiple quotes from a single application. Once quotes are received, the agent bridges over to the carrier's web portal to purchase the policy. The goal with Bind & pay is to design and build e-commerce functionality into the Terminal so agents can purchase policies for their clients without bridging over to the carrier web portal.

Final result preview

Design result features new experiences for Quote Presentation, Checkout, Finalization & Policy Confirmation

View Protype

My role, team, year and timeline

I served as Senior Product Designer on a three-person Design Team. Several additional teams contributed to Bind & pay, including:

2 Engineering Teams
1 Product Manager
1 Director of Product
1 Customer Delivery Team

I worked on designs for the Bind & pay project during Q3 and Q4 of 2024Due to the project's size, we divided the design work into several parts. I initiated the design work on Checkout functionality, which our lead product designer later completed. I also led the design effort for Quote Presentation. Throughout the project, I reported directly to the Product Manager and Director of Product while receiving valuable feedback from our Engineering and Delivery Teams.

Challenge

Bold Penguin is building this feature primarily due to contractual agreements with their corporate partner, American Family Insurance. The initial Bind & pay feature will pilot with six commercial insurance carriers (Homesite, Chubb, Coterie, Hiscox, Liberty Mutual, and Markel), with Homesite as the featured choice for quoting before other carriers can be accessed.

Open questions

How will the Quote Presentation (Shelf Page) change to accommodate Bind & pay functionality?
Can agents purchase multiple quotes simultaneously?
Will payment information be collected within the Terminal?

Status quo

From our starting point in the Terminal, here's the user's application process without any live quoting transparency:

Our solution introduces a new experience following Quote Presentation, plus updates to the Inbox page.

Process

After understanding the initial problem statement, we explored various ideas about adding functionality to skip carrier question sets and discussed where this feature should exist in the application process. My starting point was mapping out basic user flows: both the standard "happy path" through an application and what a skippable flow would look like. Next, I created light mockups comparing two scenarios: one showing an application with a single carrier's questions answered and others skipped, and another showing the traditional flow with all carrier questions completed.

We began tackling this challenge with a kickoff meeting where all stakeholders gathered to share discovery questions. As this was my first e-commerce project, I needed to familiarize myself with common terms and elements in this space. Following the kickoff, I informed stakeholders that I would create wireframes for initial concepts of our new Quote Presentation page. These concepts would then be reviewed with our Product Manager and Director of Product for preliminary feedback.

At our initial kickoff meeting, we aimed to review product documentation, understand the core problem, and create design mockups for potential solutions. The design task seemed straightforward—I planned to draw inspiration from existing insurance documents and proposals, using a template-based approach for the PDF. Our engineering manager suggested an alternative: showing how the application would look using our design system's UI components for simplicity. Though I privately thought this wouldn't work, I created a demonstration to illustrate why UI components wouldn't translate well to print format. The team ultimately agreed that UI components weren't suitable for a PDF document.

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.

The initial designs received strong positive feedback from the team. During our brainstorming session, we identified a few minor changes to experiment with. The main suggestion was to organize the application with separate columns for questions and answers, making it easier to scan down the page and match answers with their corresponding questions. We also discussed what client and agent information should appear in the header, and whether to include Bold Penguin's logo. I implemented these subtle changes within a week and presented the updated design to the team for review.

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.

Since there were no major questions during our final feedback session, we were able to finalize the designs and add the project to our development backlog. We held one refinement meeting with our engineers to discuss the designs and address questions, with only minor changes made afterward. From a product standpoint, we needed to decide on the official feature name and what to call the PDF document by default. Working with the product owner, we changed the title from "Bold Penguin Application Summary" to "Bold Penguin Documents."

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.

After handing off the checkout designs, I returned to redesigning the Quote Presentation page. Since we planned to rebuild this experience from the ground up, I saw an opportunity to create a traditional, familiar e-commerce layout. I explored both grid card and horizontal card layouts. Insurance being a detail-oriented industry, we faced the challenge of displaying comprehensive information while maintaining visual clarity. We ultimately chose the horizontal card layout and enhanced it with distinct sections. In rebuilding the Quote Presentation page, we organized it with sections for quotes ready to bind, an upsell section, and a bottom section for quotes needing attention or those ineligible. Our final design incorporated several use cases:

American Family quote feature choice option
American Family referrals for exploring other markets
Multi-carrier and multi-product options
Additional tabs for our exchange product
Commonly used ACORD forms
An Intercom button for user support

As we completed the designs for all primary screens within the checkout experience, we reached a solid foundation to discuss implementation with our development teams—focusing on how to bring this experience to life for our agents and carrier partners.

Final result showcase

Product demo of Bind & pay checkout experience

Impact

Through the final design and several refinement sessions with our Development Team, we resolved many of the original challenges we set out to address, including:

E-Commerce Goals

Looking back, this feature was very significant for us to ship because, as I would later learn, we had future goals of adding e-commerce functionality within the Bold Penguin Terminal product line. This feature was implemented at the right time to build toward deeper policy purchase functionality.

Headstart on devwork

Fortunately, since significant backend work was already complete, the development team was able to work on this epic in Q4 of 2022 and deliver it on time and within budget. I'm writing this in Q4 of 2024, and the Real-time quote eligibility feature has required very minimal design or development maintenance.

The implementation of Homesite as the featured choice for initial quotes.

The ability for agents to purchase, issue, and finalize policies for their clients while remaining in the Bold Penguin Terminal.

We created better alignment on which features to prioritize in the initial release of Bind & pay based on what matters most to our pilot customers.

Looking ahead to 2025, the team has several tasks planned for Q1 before the full launch of this product feature. As a result, we cannot yet measure the full impact of how users will receive the Bind & pay feature once it's enabled.The main goal of Bind & Pay is to fulfill our contractual agreements with American Family Insurance. While this means the team has limited priorities for monitoring the feature post-launch, we will track several key metrics in the Terminal to measure its success and evaluate this new functionality.

Number of policies bound

Terminal conversion rate

Checkout abandonment rate

After launching the initial phase with our pilot customer, our product team will collaborate with the business intelligence team to track these KPIs within the Terminal to measure success. Bind & Pay is scheduled for a V1 release to our Enterprise customers in Q2 of 2025.

A successful release will be indicated by Terminal Users downloading the Application Summary primarily when they don't receive successful quotes. We hypothesize that Terminal Users will have fewer complaints about incomplete or incorrect ACORD form mappings since they can use the Application Summary as an alternative. Here are the metrics we plan to track through the Business Intelligence Team:

Number of downloaded "Application Summaries". Track from applications with and without quote failures

Usage of "Application Summary". Number of carriers that users receive quotes from & how many quote failures they receive on average

Our engineering team started work on this project in Q4 2024, but due to recent transitions within the product team, it has been placed back in our product backlog. We plan to launch alongside the rollout of our Bind & Pay feature in Q2 2025.

Learnings

The biggest lesson I learned from this project was how to effectively hand off design work to other designers. While taking pride in our work is important, we must ultimately function as a unified team focused on shared goals. This experience highlighted the importance of aligning around a common vision in our design system—specifically through documenting theoretical principles and establishing a shared design language that enables everyone to work efficiently.

Another lesson was learning how to be patient in a project that spans several months with numerous stakeholders providing feedback. My approach was to present multiple design concept options to help us reach decisions. Often, we would choose a direction only to later return to an option we had previously dismissed, requiring us to carefully re-examine our original choices.

The biggest lesson I learned from this project was how to effectively hand off design work to other designers. While taking pride in our work is important, we must ultimately function as a unified team focused on shared goals. This experience highlighted the importance of aligning around a common vision in our design system—specifically through documenting theoretical principles and establishing a shared design language that enables everyone to work efficiently.

Another lesson was learning how to be patient in a project that spans several months with numerous stakeholders providing feedback. My approach was to present multiple design concept options to help us reach decisions. Often, we would choose a direction only to later return to an option we had previously dismissed, requiring us to carefully re-examine our original choices.

The biggest lesson I learned from this project was how to effectively hand off design work to other designers. While taking pride in our work is important, we must ultimately function as a unified team focused on shared goals. This experience highlighted the importance of aligning around a common vision in our design system—specifically through documenting theoretical principles and establishing a shared design language that enables everyone to work efficiently.

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