Fifteen years ago, when I was an editor at New York magazine, I had a little side project: I got to launch nymag.com as the site’s founding editorial director. The site’s first advertiser was Armani A|X.

Because I had scant dedicated staff at the beginning, it fell to me to solicit the advertising materials—specifically banner ads, which would go into rotation on nymag.com—from Armani’s marketing department. At the time, banner-ad specs were still a new-ish thing. Having done display ads in odd sizes for the big dial-up portals (AOL, CompuServe, etc.), marketers were still figuring out how to advertise on the Wild West of the Web itself.
The Interactive Advertising Bureau (IAB), the organization that sets standards for, among other things, banner-ad sizes, was just a year old. (Google didn’t even exist yet; it launched in 1998.) When the Armani A|X banner ads arrived in my inbox, they didn’t fit our standard banner-ad slot atop the nymag.com site template. I remember the business-side person who sold the space to Armani asking me if we couldn’t just “rework” the website to accommodate the odd-shaped Armani banner. Because they were an important advertiser and all. Um, no. (The Armani team ended up graciously resizing their banners.)

A decade and a half later, well, the more things change, the more they stay the same. Media companies that support their journalism habit with advertising have generally settled on a bunch of standards (thanks largely to the IAB), but at the same time they’re bending even farther over backwards to cater to marketers’ wishes. Advertisers are demanding, and getting, all sorts of special considerations, including envelope-pushing site takeovers (sponsor branding that temporarily blankets Web pages) and custom-content sections.

At the same time, of course, the ground is shifting for everyone, as the rise of social media, mobile platforms, apps, etc., radically alters the meaning and relevance of the cpm (cost per thousand) and the place of the basic banner ad in the Web ecosystem.
To examine how the media ad-sales business is changing with the times, I spoke with the advertising chiefs at three very different companies. First, I went back to my old stomping ground: New York, a legacy print company whose weekly magazine launched 44 years ago (I no longer have any business or editorial relationship with it). Then I went to Salon, which you might call a legacy Web company, given that it is one of the original Internet-only magazines (it launched in 1995). And finally, I checked in with Gawker Media, the company that transformed and legitimized the blog-publishing landscape; its flagship, Gawker, launched in 2002. All three are, in many ways, competitors; as such, they’re grappling with similar challenges.

The quotes below, taken from much longer conversations, have been edited for space and clarity.

Larry Burstein is the longtime publisher of New York magazine. For what was long a print-only property, New York derives an unusually high amount of revenue—40 percent—from digital.

On creating custom programs for advertisers: We do custom programs, but we don’t do them because the banner is dead. We do them because the Web is this center for innovation, and every advertiser is trying to outdo the advertiser before, and every advertiser is demanding something new that they’ve never seen before. They don’t come and say, “Hey, the banner is dead; we need something else.” They say, “Hey, we want to buy space with you, but we also want to use your site in the best possible way.” This is kind of the challenge that’s been put out in the Web world: “We want to do a buy that is 10 million impressions, but we want to do it in a way that’s never been done before.”

What a media-company promotions department now does: The promotions department—at our company, at least—has morphed into this kind of think tank and solutions group for the Web. In the past they were, like, making T-shirts and beach umbrellas and stuff like that; now they’re sitting around trying to figure these questions out.

Simon Dumenco is the media columnist at Advertising Age and a contributing editor at Details. He's a veteran of both print (e.g., he was editor of the National Magazine Award-winning media column at New York magazine and consulting executive editor on the launch of O: The Oprah Magazine) and digital (he was founding editorial director of nymag.com and founding editor of Very Short List, etc.).