For ten years, the brand has leaned on wit and charm in direct creative to connect with a single market.
Finding an apartment you love in New York City is competitive, expensive, and often fraught with drama—not to mention concessions. In other words, it’s nothing short of a miracle.
That’s something the marketing team behind StreetEasy’s ad campaigns has spent a decade trying to imbue into its work. As the company celebrates 10 years of advertising to New Yorkers, predominantly on OOH ads running in the subway, we spoke to the team about some of the brand’s defining work—and what makes it special to speak to one market.
“[We had to] make sure that we were talking to New Yorkers the way that they want to be spoken to,” Bridget Sullivan, StreetEasy’s director of integrated marketing, told us, adding that the brand was inspired by writer Fran Lebowitz’s wit for its tone of voice. “New Yorkers will call you on it if you know you’re not being authentic…We want to bring through our charm and our wit, but also our directness.”
In the early days of the brand marketing efforts, that directness often referenced the challenges of living in New York City—like proximity to neighbors, noises, and the size of an apartment—all things the team, Sullivan said, felt the brand was uniquely equipped to address.
Target market
The company’s first major ad campaign, released in the spring of 2015 and by Goodby Silverstein & Partners, featured ad copy like, “Is it still a bedroom if the bed doesn’t fit?” and “Sure, your window faces a brick wall, but behind that wall is New York City.”
The latter copy became the basis of the long-term strategy for the brand, Paul Caiozzo, former executive creative director at Goodby Silverstein & Partners, told us. Caiozzo worked on the early campaigns for the brand, first at Goodby Silverstein & Partners, and then at the shop he founded, Office of Baby. (He currently serves as chief creative officer at Tombras.)
“[It was] about honesty [and] transparency, but not negativity,” he said. “Yes, New York is hard, but behind that badness is this amazing city…That became the North Star. You can have a little bit of salt, but it always has to finish with sugar.”
The salt and sugar have shown up in many iterations over the years. As one ad from 2016’s “Find Your Formula” campaign pitched, a theoretical rental with “maybe rats,” “definitely cockroaches,” and “the other bugs with all the tiny legs” also was under $1,500 and in the East Village.
The targeted nature of the campaigns, both in audience and in its targeted OOH format, helped hone the voice of the brand,.
“New Yorkers have come to know us as the subway brand,” Sullivan said. “We actually know that our ads are up and running on the MTA before the MTA even has time to confirm it with us, because we get some type of [social post].”
The “subway brand”
Becoming known for work on the subway was no accident, according to Caiozzo, who shared that early on the team used the work of another brand known for its work on the subway, Manhattan Mini Storage, as a benchmark to beat. (And both brands, perhaps, owe something to dermatologist Dr. Zizmor, whose ads used to rule the subway before his retirement.)
Ciaozzo believes that StreetEasy’s marketing arrived at a time when OOH was “secondary” in many media plans. “Creatives didn’t like working on it, agencies mailed it in, and nobody was putting that level of effort into it,” he said.
That may have helped the brand’s efforts to be synonymous with subway advertising.
The creative team at Mother New York, which has been behind StreetEasy’s campaigns since 2024, said the subway connection adds a level of “good pressure” to make the work extra compelling, Nicole Rousseau, group account director at Mother New York, told us.
“Every friend that I have always takes pictures of the StreetEasy ads,” Rousseau said. “We want to make this as good as what we would see on the subway, and be like, ‘Yeah, that’s amazing. That is a true New York insight, not just something surface level.’”
Today’s campaigns
Over the last decade, the brand has evolved its focus from the rental market in Manhattan to the boroughs and, in more recent years, added the question of ownership to the mix.
That expansion has made the brand dig deeper. In 2024, StreetEasy released its first campaign solely pitching ownership, “Let the Journey Begin,” which used a Renaissance painting style for the ads to capture the drama and weight of the question. Since then, the company has released two more campaigns by Mother, 2025’s “Never Become a Former New Yorker” and 2026’s “Be a Forever New Yorker,” both of which are meant to inspire people to think about living situations long-term.
StreetEasy’s recent ads have had to “tap into a bigger emotional part of the process,” Rousseau said. “You have to really be able to talk about the emotional journey of, ‘Should I buy here? Should I stay here?’ That is a big decision…We had to have the balance of that insightful, clever copywriting, but also something emotional behind it.”
Whether the brand is pitching New Yorkers on renting or buying, the goal of entertaining remains the same. Evan Carpenter, group strategy director at Mother, sees StreetEasy’s effort as akin to good energy someone may put out and have come back to them.
“It’s kind of like how you live in the city,” he said. “In New York, you get what you give, and so if you are courteous on the subway, if you walk at the pace of the people, if you make some space, you kind of get a shine back…We want our ads, especially in the subway, to feel like they are like entertainment, and maybe a little bit of a moment-maker for New Yorkers.”