This week, way back in 1999, Esurance opened our digital doors. At that time, we were one of the first car insurance companies to sell policies online. And in the 20 years since, we’ve leveraged technology in a myriad of ways to make insurance simple, transparent, and affordable for our customers.

For example, Esurance Mobile lets you take care of business anytime, anywhere. Coverage Counselor®, helps you better understand your car insurance coverages. And DriveSense® helps you save money based on how safely you drive.

Point is, we’ve been using technology to make insurance surprisingly painless … for two decades!

So to celebrate this milestone, we thought we’d take a minute to look back at a few other ways tech’s helped make life SO much easier (and safer) over the last 20 years.

Smartphone maps

Honestly, can anyone even fold a paper map back to its original size?! Much less look at one while trying to drive? Not recommended! And thankfully, no longer necessary. Ever since Google Maps appeared on the first iPhone in 2007, drivers have been ditching their paper maps for safer, easier-to-use guides on their smartphones.

Backup cameras

Granted, the rearview camera may have been conceived of before 1999. But, thanks to more affordable production, they’ve exploded in popularity during the last two decades. They not only make pulling out of a parking spot literally — and figuratively — painless, but they prevent accidents and even save lives. If your current car doesn’t have one, your next one might. In fact, as of 2018, all new cars sold in the U.S. are required to have them. 


Gone are the days of waiting on hold to order a cab or standing in the street to hail one. A few taps of your phone and BOOM: your driver arrives right where you are. It would’ve seemed inconceivable a decade ago, but today it’s so commonplace that in 2018, a reported 95 million people used a rideshare app on a monthly basis.

Streaming entertainment

Back in 1999, you might’ve displayed your collection of VHS tapes, DVDs, and CDs proudly in your living room. Probably on a stand or in a cabinet you bought solely for that purpose. But alas, times change. And all that prized media is likely now gathering dust in your garage. Since Netflix introduced its streaming service in 2007, companies have raced to compete. Which means you can now stream basically any entertainment you want, just about anywhere you want. With Wi-Fi or a data connection, that is.

Robot vacuums

If you’ve ever had to push a vacuum, you can surely appreciate just how painless these little robots make it to get your floors spick and span. Whether you’re home or not. So much for wrestling a tangled cord and changing the bags and filters in a loud, clunky vacuum! Today’s robot vacuum is quieter, finds its own way around your house, and can even charge (and sometimes empty) itself. How painless is that?

All these innovations have made life easier in their own ways. And as Esurance enters our third decade in business, we look forward to continuing to do the very same thing. By making insurance simpler. More transparent. More affordable. In other words, surprisingly painless.

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about Jonathan

Jonathan is a word nerd, a food freak, and a travel junkie. By day, you'll find him weaving words for Esurance as a Senior Copywriter. But in his off time, he'll likely be digging into a new restaurant in his home base of Denver, Colorado, or white-knuckling his way down a mountainside on a weekend road trip.