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Huckleberry Application


In this first section I provide a little more context about my role at Huckleberry, the problem we were attempting to solve with the product, as well as the guiding concepts I tried to follow as I designed and built the first few versions of the product.

If you'd rather to skip to the work samples click here.


Early days at Huckleberry

What's a Huckleberry?

Huckleberry is on a mission to make insurance work for small businesses. Over the past decade, technology has changed the way we run companies—from accounting and tax prep to customer management and payment processing. But small business owners are still forced to buy workers' comp, general liability, and property insurance via an offline process that can take weeks to complete.

Huckleberry aims to change all that by offering simple, fast business insurance – powered by technology. 100% online. 100% easy.

My Role

I joined Huckleberry as its Senior Product Designer – the very first hire and only designer on the team – when the initial bootstrapped team consisted of our CEO and CTO, adding a VP of Data Science very soon after I joined.

When we were just starting out there was no existing product or branding, and no customer base – just a solid idea and an ambition to disrupt an industry. So, it was my task to build a core brand and product that could serve the company's needs and help carry it to the next level.

I continued to be the only designer on staff for three and a half years until late 2020, spearheading everything from core product UX/UI, to corporate branding, styleguide, illustrations, email campaigns, online marketing deliverables right down to company swag. I also worked closely with the dev team to orchestrate handoffs and even frequently contributed front end code and styling as needed.

The Problem

Legacy small business insurance applications are a confusing, expensive headache for business owners. The traditional process can often include as much as a 300 question form, can take weeks to get coverage, carry as much as 12% broker fees for little to no actual added value, and after all that can sometimes still end in a denial of coverage.


Guiding Concepts

In an effort to fix this predicament for our customers, Huckleberry is building an insurance company from scratch, with software at its core. Huckleberry is aiming to change the way small business insurance is done by providing business insurance products that are simple, fast, and 100% online.

Our core guiding principles were that business insurance should be:

  • Simple: Offer a simple, intuitive user experience.
  • Quick: Self serve in minutes - not days.
  • Understandable: Less insurance jargon and more friendly, colloquial language. Huckleberry talks like a real person with casual but concise tone. We're genuine, friendly, and human.
  • Transparent: Straight forward pricing – with no bait and switch.
  • Empowering: Business owners should be able to get coverage as quickly as possible so that they can get back to business.

Huckleberry Application Flow

Ver. 0.x

This an example of what the product looked like in the very early days – before we’d even settled on our font or wordmark! At that point it was essentially just an online version of the same lengthy form that legacy insurance carriers had. It was still pretty confusing and full of insurance jargon most users wouldn’t understand, and in terms of design, many things still weren't quite working...

The Card System

In an effort to solve many of the problems with the first iteration of the application, I designed the card system: A core interaction of the Huckleberry product.

The basic guidelines were:

  • 1 question per card
  • 1 card at a time
  • Questions / instructions as plainly worded as possible – no jargon
  • A simple form or interface enabling the user to answer quickly, and move on
  • Clearer indication of overall progress through the application
  • A sidebar with dynamic pricing and a user profile that updates in real time based on actual information gathered / entered

By following these guidelines I hoped to make a really long, onerus form easier for our users to get through and hopefully just a bit more delightful.

Ver. 1.x

This was the first iteration of the product that integrated the card system concept. Testing was done through a combination of anecdotal feedback from stakeholders & investors, user testing, user research, Google analytics and HotJar.

Feedback to the changes was generally very positive, however, some users still noted confusion and/or frustration with overall length of process and clarity of progress indication. It was also noted that many business owners wanted a ‘one stop shop’ where they could take care of all the insurance their business needs in addition to Workers’ Comp.

Ver. 2.x

In this next iteration I raised the visual contrast between cards and background to bring more focus to question cards and increase overall visual interest. Additionally, I added a 3D “card stack” animated effect when moving between cards to better signal progress through the flow as a subtle visual cue. And, a new visual treatment for the progress bar at the top of the screen was introduced to help with visibility and unify design elements.

On top of these visual changes, we continued to further refine and simplify the question verbiage and sequence. And added an additional product line: “Business Owner’s Policy”.

Huckleberry Application Flow: Takeaways

With each new iteration, user and stakeholder feedback has remained very positive. Conversion and policies sold continued a distinct upward trend and the company secured an $18M Series A based on the strength of the product.

Huckleberry Application
Year: 2017 – Present
Client: Huckleberry

  • Walker Design Did:
  • Product
  • UX
  • UI
  • Visuals
  • Logo
  • Webdev

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