Lets face it, less than 1% of Web readers click on an average banner ad. The ad industry is trying to fight “banner blindness.” Internet publishers are pumping out increasingly large volumes of content in order to obtain decreasing amounts of ad-click revenue. Ad-blocking programs drain billions of dollars from the industry, and media-rich ads have proved to be just as uninviting: 94% of people skip pre-roll video advertising as soon as they can.

The more personal the ads can get the more likely we are to click on it. In the past several years advertising strategy has shifted toward social media and smartphones—two customized and conveniently overlapping spaces. Twitter offers sponsored tweets; Instagram is projected to bring in $2.81 billion in ad revenue in 2017; Snapchat has been experimenting with sponsored filters—one promotion featured Slimer, from “Ghostbusters,” bouncing around in the foreground of your selfie.

The last frontier, at the moment, is private mobile messaging—an arena we think of as inherently trustworthy, in part because it has, until now, been ad-free. WhatsApp, a messaging app owned by Facebook, has tested limited corporate promotions, and Facebook Messenger has unveiled branded chatbots: you can ask 1-800-Flowers for bouquet recommendations, for example, and order flowers without leaving the exchange. Just this month, Google began rolling out click-to-message ads, which prompt customers to open pre-written text messages through ads viewed on mobile browsers. (A sample message, generated by an ad for Westin Hotels, tells the company, “Hi, I’m interested in a reservation. Please text me back.”)

 How playful, charming and natural can ads on mobile messaging be?

 Travis Montaque is the C.E.O. of a startup called Emogi, which has raised four million dollars to date, and which currently has twenty employees. He was just added to the list of Forbes’s 30 Under 30, In his view, the future of mobile advertising is intertwined with one of the most delightful aspects of texting, which is emoji. He’s betting that branded emoji will be even more fun than regular emoji. He thinks we’ll like them so much so that we won’t mind that they are trying to sell us things.

 Emogi recently launched a branded-emoji platform, called Wink, Wink looks like the standard emoji keyboard that comes with any smartphone, but it’s loaded with a changing array of branded emoji, which pop up above the regular keyboard depending on what a user types. It’ll work like this:

A beer brand—let’s say Bud Light—makes an ad buy on the triggers “party,” “drinks,” or “?.” The brand then targets the users in the demographic they’re going after: women aged eighteen to thirty-five in New York or Chicago, say, whose Internet profiles indicate that they’ve recently searched for local bars. When these women text their friends “??,” a selection of Bud Light emoji will pop up in their keyboards: a girl riding a beer can like a rocket, perhaps, or a frog sipping a Bud Light, or a ? clutching a beer in both hands. Ideally, these little images will be too charming to resist.

Montaque was quick to clarify that Wink won’t record text messages. But it will record data around the triggers that provoke branded emoji, and match that data to the information attached to your device I.D.—your location, your internet profile, the number of devices you’re in communication with. As a service to the brands, it will quantify all of this in real time.“You kind of get an understanding of the types of emotions people are having throughout the day. . . . Like, if a person is sending a heart at a particular moment, you have a geolocation, you have all these other things, you know that at that moment in time this person was excited or they were thinking about coffee at this place,” Montaque said, with visible excitement. “Wink is just a key for brands to get in the door. We’re going to give them more things as they walk through. We’re going to figure out all the ways they can leverage the data.” Montaque evinced none of the horror some of us feel when we remember how much of our online activity is being tracked and analyzed.

A handful of brands have already tried to break in to branded emoji, releasing single-serving keyboards: in 2015, for example, Burger King made one to promote the return of Chicken Fries. The emoji were cute enough—a series of tiny Chicken Fries boxes, winking and blushing and streaming joyful tears. But you’d have to maintain a troubling obsession with Burger King to use the fast-food chain’s emoji on a regular basis.

Will you incorporate this into your marketing strategy?