by Zak Stambor, Internet Retailer

The Internet pioneer’s acquisition of Polyvore is the latest in a series of moves aimed at helping marketers reach millennials.

Yahoo Inc. CEO Marissa Mayer is betting she can turn around the Internet pioneer’s fortunes by figuring out how to help marketers reach millennials.

The task isn’t easy, particularly given the company’s dwindling financial results; Yahoo posted a $132.1 million loss in the first half of the year, which compares to a $68.6 million gain in the same period a year earlier.

Mayer’s plan requires a deep understanding of native advertising—ads that match the style and function of the platform on which they appear—says Brian Solis, principal at research and advisory firm Altimeter Group. “Millennials don’t want to see ads, they don’t want to see retargeting ads, they don’t want to see the lame types of marketing pieces that brands have long used to try to lure us to buy,” he says. “They want editorialized, lifestyle content that communicates experiences.”

That’s that the specialty of editorial, content-focused sites like BuzzFeed and Vice, as well as social networks like Facebook, Pinterest and Yahoo’s newest acquisition, Polyvore, he says.

“Native advertising is difficult to figure out,” he says. “It’s very nascent and it’s hard for brands to figure out how to create what type of content to produce and where to make strategic buys to place that content.”

But Yahoo’s ad-buying platform Gemini, which it introduced in February 2014, aims to change that. The self-service ad-buying marketplace is Yahoo’s attempt to persuade marketers to use Yahoo data to buy native and video ads both on Yahoo-owned sites like Tumblr and thousands of other sites and apps across the web.

“Native … is a torrid growth pace,” Mayer said during Yahoo’s first-quarter earnings call, noting that Gemini generated $110 million in revenue in the first quarter. “Overall the ecosystem is performing really well. We haven’t quantified it but we certainly have thousands of advertisers in Gemini. They’re incredibly well-targeted ads because those ads are great for advertisers because they can create them easily, they’re text ads, they can add a picture or not, and you can actually quantify the return on investment really easily because you pay on a cost-per-click model.”

In acquiring Polyvore, Yahoo is adding yet another platform where retail marketers can use native ads to appeal to consumers, Solis says. Polyvore, he notes, gives Yahoo some inventory centered on e-commerce.

Even so, at least one analyst isn’t convinced that the Polyvore acquisition will pay off for Yahoo.

“Polyvore isn’t the property that Yahoo needs to be relevant in a world where we’re seeing platforms like WhatsApp and Snapchat explode,” says Lou Kerner, a social media analyst and investor at The Social Internet Fund.

While Polyvore is a social network with an e-commerce bent, its user numbers are relatively flat, according to mobile app measurement firm App Annie. That’s a problem as mainstream social networks like Facebook, Instagram and Pinterest push into e-commerce by enabling marketers to sell directly on their platforms.

“The pendulum is swinging from consumers navigating the Internet to their spending time in walled gardens where they can do everything they want,” Kerner says. “If you can read articles, watch videos and shop on Facebook, why would I go anywhere else? That move may marginalize niche platforms like Polyvore.”