What’s the new frontier for targeted online ads? Could the long tail go bankrupt? What does social media offer that social networks don’t? Publishers, advertisers, and service providers flocked to ad:tech at the Javits Center in early November for three days of 60 panels and presentations to find out what’s working—and what isn’t—in online advertising.

Facebook claims that 50% of its 300 million users return to its pages every day and share 2 billion pieces of content every week. Individual users, fan- and event-page owners can all use Facebook’s new upgraded self-serve Ad Manager to create a variety of targeted pay per click (PPC) ad campaigns. As Online Sales Manager Sarah Smith explained, you can target structured data like location, age/birthday, gender, education, relationship, sexual preference and language—or keywords related to unstructured data like activities, interests, groups, and favorite music, TV shows, movies, and books. Owners of fan pages can even put a widget in their e-mails so that people can sign up as fans from within the e-mail. Companies with multiple ads can use the bulk upload tool to optimize keyword targeting. Smith reported that promo codes and questions in text ads have increased clickthrough rates. Surprisingly, including “% off” depresses response.

New moms are quick to use social media to find information and help schedule their busy lives according to marketers from BabyCenter, iVillage.com, and Nielsen. “91 percent of moms won’t leave home without their cell phones,” reports BabyCenter Group Publisher Michael Fogarty. BabyCenter earns mothers loyalty with its free text message service, “Booty Caller,” timed to their ovulation cycles. Fogarty also revealed the ways that having a baby changes mothers’ clothes shopping preferences. Highest-ranking purchase criteria before baby were design, self-expression, color and sex appeal. Post-baby, mothers look for comfort, price, versatility, and ease of cleaning. 81 percent of moms say the internet has made them more informed about health issues. Targeted social media like the mom blogs on BabyCenter and iVillage perform a service larger social networks don’t. When a mother asked “When do I tell my child there’s no tooth fairy?” on Facebook, she received snarky responses. Asking mom blogs the same questions prompted shared experiences and sympathetic advice. According to iVillage EVP Jodi Kahn, the 166,000 posts about Twilight on iVillage became a way for parents to discuss sex with their sons and daughters.

Patrick Keane, CEO of Associated Content, echoed the findings from mothers: advertisers are beginning to appreciate the ways in which social media, like subject-specific blogs, differs from social networks like Facebook and MySpace. “Social media has an authenticity social networks lack. We’re not just strippers and truckers,” said Keane. His panel explored whether “the long tail will go bankrupt” as major media companies develop online content more aggressively and content of all kinds proliferates. Fellow panelist Jennifer McClain, VP Marketing at Technorati, shared some sad news: Only 28 percent of bloggers are making any money from their blogs, and only 17 percent of those are able to support themselves. Technorati is trying to help. It can build custom ad networks for advertisers across its 28 social media sites using an inventive ad unit McClain calls a “conversational ad.” (See examples on its new Google Android channel.) Andrew Rutledge, VP Sales at PubMatic, estimates that within the next three years, 34 percent of ad revenue will come through ad exchanges and networks like Technorati’s.

Advertising content must compete with online content, and Showtime’s SVP, GM Digital Media Robert Hayes recommends finding out who is popular online and partnering with them. To promote The L Word, Showtime turned a popular video blogger into “Lesberado” and got millions of views. For Californication, they tried something different: fill-in-the-blank YouTube videos that test fans’ knowledge of the show’s catchphrases.

“The time for listening is over. The buzz word now is ‘engage,’” according to Matt Singley, Senior Director of Social Media Marketing at M80. He and Microsoft’s Paul Chang offered a case study of how to market a product—in this case, the Microsoft Zune—on Twitter. They found that thirty percent of online conversations about the Zune came from Twitter; Zune now has 11,000 followers and almost 25,000 Facebook fans. So, what does engaging entail? Singley and Chang say that companies must friend those who follow them so that they can have direct message conversations offline. They need to acknowledge the positive and the negative and respond, reaching out to influencers and participating in fan communities. And they must retain customers through sweepstakes and promotions.

Time has 1.7 million followers on Twitter, but follows only 92 users—“influentials,” Time.com GM James Cantarella calls them. One thing Cantarella heard when he listened was that Time’s Twitter followers did not like their newsfeed filled with a thirty-minute live Q&A with Ashton Kutcher. Time now has a separate account for live chats with newsmakers and celebrities. Time also changed its URL shortener from bit.ly to StumbleUpon’s service, su.pr, because it syndicates some of the stories it shortens.

Syndicating content was one of the “15 ways to grow your audience” suggested by panelists from Mashable, Real Girls Media, Metacafe, and Waterfront Media. They also suggested creating a “link love” column;  enabling social sharing tools (Mashable just enabled an “amoeba bar” so visitors can share an entire page); commenting on other sites; building relationships with influencers; and creating iPhone apps. WhatToExpect.com created a “What to Expect Pregnancy Tracker” app that first-time moms get free when they sign up. They credit it with enlisting 1500 new users every month. Finally, never forget SEO, warned Mashable COO Adam Hirsch: Keywords for any article should be in the first paragraph and in tags.

“What people don’t get about search” could have been the topic of several panels. Ryan DeShazer, Global Director of Search Marketing at Gyro:HSR, lamented that organic search drives more than ninety percent of search traffic but receives less than five percent of the advertising budget, mainly because CMOs view organic search as an operating expense rather than a marketing investment. Bruce Clay, a regular ad:tech panelist and SEO and internet marketing expert, wondered why over 325 million web pages have no titles (and another 300 million are called “insert title page here”). Clay noted that search opportunities increase constantly. For instance, Google now indexes videos, and even text within Flash videos is searchable if it’s static. Clay advised, “Pages should be structured in silos: theme-aligned content paths with clear relationships to surrounding pages.” Read his blog here.