Huckleberry

Huckleberry offers simple, fast business insurance—powered by technology. 100% online. 100% easy. Acquired by Paychex, 2023.

Huckleberry product screen examples

Huckleberry is an online platform that allows small businesses to purchase workers’ compensation insurance and other business lines in under five minutes. Designed to streamline an outdated process, it provides a fast, transparent, and user-friendly experience for entrepreneurs.

The Challenge

As the first hire and founding designer, I was tasked with establishing the company’s brand and product from the ground up. This involved creating a scalable and user-friendly insurance platform that could disrupt a legacy-dominated industry. The goal was to design a seamless 100% online quote flow, build trust through branding, and deliver a product that could scale rapidly while meeting the needs of small business owners.

The Outcome

  • Conversions and policies sold continued a distinct upward trend at 30% month-over-month growth.
  • Secured an $18M Series A based on the strength of the product.
  • Strengthened the product and brand, leaving a lasting impact that contributed to the company’s subsequent acquisition by Paychex.
Hucksters at the office
Intuitive Quote Flow
 

Intuitive Quote Flow

The traditional insurance process is often seen as confusing and time-consuming. To address this, I designed a step-by-step quote flow that reduced friction points and provided contextual guidance. This simplification led to a significant increase in completed self-serve applications without the need for human intervention.

Video by the awesome folks at

Made by Things Logo
 

Distinct Brand Identity

I established Huckleberry’s brand identity, including logo design, typography, icons, color systems, and corporate voice to stand out in a crowded insurance market. By emphasizing accessibility, friendliness, and warmth in a traditionally more stern industry, the brand successfully balanced professionalism with approachability, creating a lasting impression with users and investors alike.

Branded Swag Design
 

Branded Swag Design

I extended Huckleberry’s visual identity into company swag, designing custom apparel, stationery, printed materials, and promotional items that embodied the brand’s approachable and friendly tone. These efforts not only fostered team pride but also enhanced the company’s presence at industry events and investor meetings.

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