Before we began, Progressive was the #1 commercial auto insurer in the U.S. – so we were starting from a position of strength. But we had a challenge ahead: grow Progressive’s direct commercial business by compelling business owners to quote their insurance online.

The problem? Most business owners delegate their insurance decisions to agents; commercial insurance seems too complicated and high stakes to purchase without professional help. Compounding the challenge of our non-traditional call to action was the level of noise to break through. Insurance is one of the most saturated advertising categories in America.

Our final challenge? Ourselves. For 15 years, Flo has become synonymous with the Progressive brand. We needed to create a distinct campaign that was specific to business owners, but still recognizable as Progressive.

The ask? Develop an integrated campaign that compels small business owners to quote their commercial auto and business insurance directly with Progressive.

The weight of a to-do list, universally felt, bears down particularly heavily on small business owners (SBOs). This ceaseless list serves as a constant reminder of the multitude of tasks demanding attention each day. For SBOs, this burden can take on a life of its own.

Enter the Monster To-Do (MTD)—a whimsical embodiment of the SBO's list, characterized by its intrusive and persistent nature. This clumsy, irritating sticky-note blob knows no boundaries of personal space, reminding SBOs of pending tasks at the most inconvenient moments. But one task —obtaining a commercial auto quote from Progressive for potential savings—that is so quick and easy, our SBO tackles it right then and there with ease.

While the MTD lives on television, our Print and Radio campaigns echo its theme, acknowledging the absurdity of SBOs' to-do lists. This integrated approach addresses the challenges faced by SBOs while promoting Progressive's solutions.

Our audience is comprised of micro-small business owners, typically with 0-10 employees, relying heavily on commercial vehicles for operations.

For SBOs, their business is their baby, so they have their hands in everything. Their to-do lists are endless, leaving them constantly pressed for time, racing against the clock. Asking them to add one more thing, like obtaining a quote from Progressive, poses a challenge for our brand. Shopping for insurance is a daunting task that often lingers on their list or never even makes it there.

Strategy: With Progressive, saving money on insurance – which seems like it should be a time and energy-sucking hassle – can actually be quick and easy with an online quote. Which means, small business owners can get right back to taking on all of their other to-dos.

In “Monster To Do :30” we personify a to-do list as an actual life-sized character that reminds the small business owner of all things he needs to get done in a day. But before he can even remind him one thing—to get a commercial auto quote from Progressive—our SBO has already done it.

In print, we continued with the stickies as a way to visualize the SBO’s never-ending to-do list. Our executions featured a variety of SBOs running their respective businesses, but the sticky notes kept getting in the way. The one thing that wasn’t a hurdle – getting a commercial auto quote with Progressive.

Radio further drew on that insight of an SBO’s nonstop monster to-do list. Similar to print, the executions focused on dialing up ease messaging to communicate to SBOs that while tackling to-do list can be difficult, getting a quote with Progressive isn’t.

According to copy testing results, the MTD campaign demonstrated remarkable efficacy in breaking through and generating impact for Progressive among SBOs, surpassing the performance of prior campaigns targeting this demographic. It effectively instilled a lasting, branded impression among SBOs, with viewers concurring that Progressive simplifies the entire commercial insurance process, prompting tangible behavioral shifts.

We care about business results at the end of the day. Progressive's commercial business exhibited exceptional performance overall during the campaign run. Note, the MTD campaign was the only mass advertising running for Commercial Lines at the time. By the close of 2023, Progressive had maintained #1 market share for commercial auto and amassed triple the market share of its closest competitor, a trend that persists into the first quarter of 2024, signaling continued growth. Tying back to the campaigns CTA, Progressive also witnessed substantial growth in direct premiums written during the campaign run YoY.