Over the last three years, Ladder has focused on a brand filled with delight. Everything from the layout to the tone was centered around making life insurance more approachable. As the system became more complex, and we learned from each new user interaction, we decided that it was time to enhance our brand identity, therefore implementing a more profound user experience.

Why Rebrand?

Right now, Ladder’s brand focuses on delight. The brand implementation uses light, clean, task-focused layouts with feel-good illustrations and a straightforward tone, leading with mottos like “Instant. Simple. Smart” and “Life insurance you’ll love (really).” Users responded positively as we made a heavy topic feel more approachable, but there were more powerful motivational forces that we wanted to tap into. We were searching for a look and feel that would take us into the next phase of Ladder’s maturity.

Our goal with this rebrand was to create a sense of authenticity, connectedness, and reliability. While many values were considered, the team boiled it down to Wholeheartedness. This word was then broken down into more actionable definitions that helped the rebranding team work through each phase of this project.

A Visual Evolution

The following is a collection of my contributions to the new branding guidelines.

Setting Expectations. While there were a ton of design discussions, branding team discussions, brainstorms, post-it note sessions, style narrowing meetings, and more, the following will only show the progression of my contributions, focusing on UI explorations, over the course of the rebrand. These explorations, in conjunction with the rest of the design team’s explorations, led to the new brand designs and guidelines.

Frame

Mood Board. The design team, including myself, guided a larger team exercise to decipher how we interpreted the word ‘wholehearted.’ Each participant brought images and words that related to this term.

Adding To It. After the session concluded, I found that we could add several different types of elements to the mood board in order to make it feel more complete and set the tone that had been discussed in the session. In order to achieve this, I digitally recreated the mood board adding:

Expanded The Board. As I added to the mood board, the group mixed, matched, and grouped the images. We identified key attributes of what it means to be wholehearted. Words that bubbled to the surface were authentic, self-forgetful, and connection.

Image Styles. Having discussed the use of photos rather than illustrations in our new brand, I spent time gathering images to start determining attributes and feelings that would define the new guidelines.

Identity Brainstorm. In an effort to identify a targeted user group and a unique brand identity, I facilitated a mini workshop for the design team to clarify our user promise, vision, and guiding principles.

We gravitated toward some key brands, including: Slack, Allbirds, Lemonade, Third Love, Oscar Patagonia, Acorns, Care/of.
We also determined some unique promises for ourselves, including:

• To do right by the user

• To create reliability and confidence throughout the user experience

• To remove the fluff, providing more of what the user needs

Constrain

Competitive Analysis. Having started the process to better understand what type of brand we wanted to be, I looked to other major brands to learn how they embodied their values and images.

Emulation. When rebranding, there’s really no good place to start; it’s just important to start somewhere. So, in an effort to see how different layouts and picture styles could work, I imitated several well-branded sites with mid fidelity mocks.

Themes. By referencing the identity workshop, image collection, and competitive exploration, I organized and developed some possible themes.

Explore

Concept 1 Exploration. The design team reconvened to come up with ideas about how we could distinguish ourselves among other brands. We each chose a direction that allowed us to start experimenting with our homepage. My concept involved speaking about death directly.

Picture Attributes. The more I explored, the more I refined the type of imagery I was drawn to. I landed on a concept that I called ‘Millennial Moments.’ These included high-energy moments with authentic connections between actors in each photo, meaning they seem to be focusing on their own lives, in the present.

Millennial Moments. The millennial moment photo style inspired the next iteration of my exploration.

The Next Step. In order to move forward with a single concept, each designer chose a concept and would present a homepage, an application question, an email template, and Facebook ads to the branding team. In order to prepare, I collected samples of interesting question concepts and email templates. Then I worked through iterations of each deliverable.

Stakeholder Presentation. I ended up presenting the ‘In Focus’ concept, using a more editorial layout that focused on a younger demographic and guided the user through the intended thought process, creating a storyline facilitated by the dynamic lines.

Focus

Shapes. With the decision to utilize the Blocks concept, because of its grounded-ness and use of studio quality photos, the design team opted to explore our options widely again, looking at all types of shape stylings.

Shapely Concepts. This exploration led to numerous iterations in the shapes space, looking to create the right feel. In order to compare apples-to-apples, we all used the same basic elements and layout in our mockups.

Choosing A Direction. The team regrouped to choose a direction from three of my concepts and three of Kyle’s concepts. We anonymously voted and landed on two: Spotlight and Confetti.

All six final concepts:
Spotlight: https://invis.io/MKVBN2KGFPS
Confetti: https://invis.io/TNVBN2S6DR2
Blobs: https://invis.io/KAVBP0QC53R
Highlights: https://invis.io/E2VBP1BN6AV
Flairs: https://invis.io/NHVBP1JFYZ5
Frame: https://invis.io/3TVBP1LS6QZ

User Testing. With two directions, I advocated to test with real people, which would emulate an organic traffic source. I wrote a test plan with feedback from the team, mostly testing each concept separately. The outcome of this study showed that the Spotlight concept evoked the thoughts and feelings that aligned with what we wanted our new brand identity to be across genders.

Check out the test script.

First Iteration. Having chosen a direction, we were finally able to start focusing on the details.

Define

Photography. We knew that photography would play a key role in setting the right tone. We landed on two well-known photographers, Peter Samuels and Brayden Olson.

Peter’s style used strong visual eye contact in a professional studio setting. It created an authentic feeling of depth with real human beings. On the other hand, Brayden’s style was younger, more exciting, and took place in more real-world settings. It played on the interconnection of actors in the photos.

We ended up going with Brayden in order to create more visual contrast with the super sophisticated, neutral look we selected. This would generate more energy for users going through the experience, which was similar to the Millennial Moments style I had previously explored.

Brayden Olson Photography

Illustration. We wanted to supplement the photography with another type of imagery in order to round out the look and feel while also providing more diverse options when redesigning pages on the site. After significant research, we stumbled upon a set of illustrations in an image drawn on a coffee shop sign on the street. We were able to locate the illustrator by extracting one of the illustrations from the image and performing a reverse search.

New Design System. I wanted to make sure that we documented each of our design decisions and built our brand implementation from an atomic level up to fully designed components. I led the exploration and formation of the new design system, utilizing several established design systems to guide our organization, including Polaris, Uber, and Pajamas.

The Happy Path. While the design system and base elements were not anywhere near complete, we decided to divvy up the touch points within the main user task flow. I redesigned and explored everything from the question pages to the account experience, and a couple of other pages here and there.

Question Exploration

Offer Page Exploration

Post Take Exploration

Account Experience Exploration

New Product

Redesign vs Reskin. As each of us worked through our pages in the new brand, I kept asking if we were redesigning or re-skinning. The difference is that a re-skin makes our existing pages and functionalities look new, while a redesign rethinks how the flows, functionalities, and messages can enhance the experience to match the new brand that we want to reflect onto our users.

The team agreed to redesign the user experience, which would give us the range to scope down to a re-skin, if needed.

This resulted in a ton of product thinking and notable projects, including 1) updating our information architecture, 2) reshaping the account experience, and 3) defining our policy onboarding process that we would test in our current brand first.

Information Architecture. This project started by looking at how we could direct users more efficiently when they first land on the homepage. I started by collecting a competitive analysis, pulling insights about best practices currently occurring online, and then moved into exploration. The final design limited top level links to focus users on one of two paths: start an app or learn about life insurance. Everything else would be nested or linked from a block below the fold.

Account Redesign. When thinking about how the new brand could improve user retention over a possible 30 year period, I knew that the account experience needed to be redesigned. Similarly, I started by analyzing how other companies organized their account pages, then I began iterating with the functionalities that were already in place. By focusing on creating a scalable solution by breaking each aspect of the existing account onto a separate, task focused page, I was able to achieve greater clarity and opportunity for personalization and engagement for the user.

Policy Onboarding. As I began iterating over the confetti page, which is the experience after a user has accepted a term offer, I found that we could be more directional by increasing beneficiary set rates and spouse connection applications. Instead of taking users to the account in order to complete next steps, users would be guided through a series of dynamic pages to help them complete the next primary task.

My Growth

Collaboration Elevates. Throughout the rebrand, I worked closely with my design team and the larger branding team. While we explored separately, much of the conceptualization and rationalization was done together, building on each other’s ideas. Each round of iteration we borrowed from one another, seeing how we could both integrate ideas we liked and iterate on novel thoughts sparked by others’ efforts. When we finally decided on a brand identity and path forward, it was apparent that it was the collaboration and meshing of perspectives that ignited concepts that never would have been considered otherwise.

A Fresh Lens. Before designing in the new brand, it felt like the product team was a bit stuck, like there wasn’t much left to do to update the site in a significant way. It felt like anything and everything had been tried. However, as we began to design each touch point in the new brand, it’s like our eyes opened to a world of opportunities that we couldn’t see before. For example, as I explored the retention experience, I identified that there was no space for growth, but the new brand gave me the space and justification I needed to completely overhaul it. It just goes to show that nothing is ever really complete; you might just have to shake things up to see where the opportunities for design truly lie.

Expect To Be A Different Designer. Although I really like where we ended up now, I didn’t always feel that way. Throughout much of the project, I voted for other directions, whether that be brighter colors, more real imagery, showing depth, or catering to a more youthful audience. Much of what I was planning on using didn’t make the cut, but that’s ok. By pushing my own aesthetic to work on visuals outside my comfort zone, I was able to learn from different perspectives and grow significantly as a visual and brand designer.

Process Pictures