Challenge

Thimble, a new player in the small business insurance space, set out to disrupt a category dominated by sameness — talking animals, catchy jingles, and overproduced metaphors. The task: launch the brand and break through a sea of noise by proving that insurance could actually feel modern, relevant, and useful.

Insight

For freelancers and small business owners, traditional insurance feels outdated — paying for coverage even when you’re off the clock doesn’t make sense in a gig-based world. The opportunity was simple but powerful: highlight the absurdity of paying for insurance when you’re not getting paid.

Idea

We flipped the script on the industry with a straightforward, self-aware launch campaign that said what every small business owner was already thinking. No mascots. No gimmicks. Just honest, funny storytelling that dramatized the contrast between traditional coverage and Thimble’s “on-demand” model.

And in true Thimble spirit, we insured our entire shoot through Thimble — because why not walk the talk?

Impact

The campaign cut through an oversaturated insurance market with one of the category’s most refreshingly simple campaigns. It established Thimble’s tone and brand voice — smart, bold, and human, and helped position Thimble as the go-to solution for freelancers and small business owners seeking flexibility and control.