Esurance was founded in 1999 by Jean-Bernard Duler, Jeffrey L. Goodman, Huyen Bui, David Griffin, and Charles Wallace, and became one of the first insurance companies to sell policies directly to consumers over the internet, instead of using in-person meetings or phone calls.

Esurance, which is based out of San Francisco, had by that time expanded to offering policies in 24 states, but had also just laid off staff and was actively soliciting a purchaser.

The commercials featured an animated character named Erin Esurance, a pink-haired spy inspired by Sydney Bristow from the television show Alias.

It emphasized efficiency and positioned the company as "Insurance for the Modern World"; the target demographic was families and professionals in the 25–49 age group.

The company has sponsored a number of sporting events and teams, including the US Open tennis tournament, the Golden State Warriors, and the San Francisco Giants.

[17][18][19] In February 2015, Esurance released their Super Bowl XLIX commercial, featuring Bryan Cranston parodying his Walter White character from Breaking Bad.

[21] Esurance introduced a new ad campaign featuring Dennis Quaid (in his first-ever appearance in a commercial, and the company's first use of a real-life spokesman) as a tongue-in-cheek "highly likeable" spokesperson in August 2018.