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So What Do You Do, Jimmy Pitaro, Vice President of Yahoo! Media?

Rising through the ranks at Yahoo!, this digital chief discusses new ad revenue strategies and why free will always beat paid content

- March 3, 2010
If you haven't visited one of Yahoo!'s content sites recently, you're almost in the minority. Yahoo! News, Yahoo! Finance, and Yahoo! Sports are all number-one in their categories. (Yup, despite all the hubbub around Google News, Yahoo! News actually trumps them.) And, combined with Yahoo! Entertainment, the sites get about 81 million visitors a month according to comScore. Helming it all is Jimmy Pitaro, the vice president in charge of Yahoo! Media, whose job it is to decide how to program and package the content. Historically, much of the focus has been on aggregation and licensing of third-party content. These days, Yahoo! is investing more in original material, as with the hire last fall of Talking Points Memo deputy publisher Andrew Golis to build a blogging team for the News property and the recently announced deal with Ugly Betty and The Office executive producer Ben Silverman's new Electus production house to create Internet-native shows.

Pitaro is a Cornell graduate and former lawyer who came to Yahoo! as part of the Sunnyvale company's acquisition of online music site Launch Media. In 2006, former television executive and then Yahoo! media chief Lloyd Braun put Pitaro in charge of Yahoo! Sports, which Fast Company subsequently called "the best Cinderella story" in sports news. Pitaro's bosses must have agreed. In 2008, they handed him the keys to Yahoo! Media as a whole.

Pitaro talked with about what Yahoo's learned about what its users -- and advertisers -- want online, why free will beat paid, and what Yahoo! is looking for in the few good writers it's hiring.

Name: Jimmy Pitaro
Position: Vice president and head of Yahoo! Media
Resume: From 1994-1999, was a lawyer for Marshall, Conway & Wright and Wilson Elser Moskowitz Edelman & Dicker, both Manhattan-based litigation firms. Served as vice president and head of business affairs for and Yahoo! Music (which acquired Launch) from 2000-2005. In 2006, became vice president and general manager of Yahoo! Sports and was elevated to vice president and head of Yahoo! Sports & Entertainment (Movies, TV, omg!, Shine, Music, Games) in 2007. Named vice president and head of Yahoo! Media in 2008.
Birthdate: August 2, 1969
Hometown: Scarsdale, NY
Education: Cornell University; St. John's University Law School
Marital status: Married, two children
First section of the Sunday New York Times: Business section
Last book read: Moneyball: The Art of Winning an Unfair Game by Michael Lewis
Favorite TV show: The Tudors and 24
Guilty pleasure: "Gadgets, including everything Apple-related and home theater products."

Tell us about the deal with Electus. When are we going to start seeing content from that?
Hopefully very soon. It depends on the advertiser. Historically, we've created content that is 100 percent based on audience needs. In this deal, the idea is to focus on content that really meets advertiser and audience needs: identifying key sponsorship partners, identifying content that could work well for them, and then determining if that content could resonate with our audience.

You're not going to see us launch any content that we don't think is going to work for our audience. If we have something we think is really great for a particular advertiser, but it's not going to work for Yahoo! Sports, for example, we're not going to launch that. Because it's not going to work, and it's ultimately not going to work for the advertiser.

"We don't want to walk into meetings with advertisers and say to them: 'Here are the standard display units we have. Please buy them.' Those days are over."

So are we talking three months? Six months? A year?
I'd be very surprised if we didn't have some content that has been generated by Electus with an advertiser on board within the next six months.

The idea of creating content by starting with the advertiser seems counter-intuitive. Why does it make sense to you?
It's just a piece of the puzzle. We still have a Yahoo! Originals team that is 100 percent focused on creating content for our audience, and then going to market with that content and bringing a sponsor on board. Historically that's what we've always done, and we've had a lot of success.

It sounds like advertisers are increasingly unhappy with the conventional avenues for marketing themselves online. Is that the case?
Advertisers are just tired of sitting down in meetings with digital media companies and digital distributors and being pitched on standard large rectangular ad units that have very low click-through. They want creativity. They want innovation. And they want better brand integration. So we're being proactive. We don't want to walk into meetings with advertisers and say to them: "Here are the standard display units we have. Please buy them." Those days are over.

Dunkin' Donuts came to us and said, "We're all about the coffee, and we really want to go after our customer first thing in the morning." So what we started to ideate with them, to come up with a program that could work for them. After an hour of discussion, we realized that we wanted to go after our user first thing in the morning, because Yahoo! is all about being a starting point. So we started to talk about Yahoo! Sports and how we could get that sports fan. We came up with this show called "Yahoo! Sports Minute." It's a recap of what happened last night or yesterday in sports. The Dunkin' brand is integrated into the program, but what's important is that we created a new environment. It wasn't just a pop-up video player, or a player that was embedded in an existing page. We created a new micro-site for Dunkin' Donuts. Within that page is a Dunkin' Donuts locator. So it's that type of product that's innovative and is taking the next step in terms of how we meet advertiser needs.

"Our audience wants quick snacks. They're not that interested in consuming 22-minute sitcoms or one-hour dramas."

Your wrap-up shows -- "Prime Time in No Time," "Yahoo! Sports Minute," etc... -- there's no analog for that in the old-media world. It's an entirely new beast. Why does that work for your users?
All of our data tells us that our audience wants quick snacks. They're not that interested in consuming 22-minute sitcoms or one-hour dramas. The key point, though, is that we program based on audience insights. If you look at how "Prime Time in No Time" and "Tech Ticker" were launched. They were really low-risk opportunities for us. What we saw in entertainment was that, the morning after American Idol or Dancing with the Stars, search volume around those shows exploded. People wanted to know what happened last night, who got voted off. We were constantly reacting and producing stories around the content, scratching and clawing to find stories from content partners.

We found it wasn't really scaling, so we decided to just create programming that met that audience need. "Prime Time in No Time" was launched to address our users' huge appetite for knowing what happened last night in reality television. With "Tech Ticker," we saw a lot of interest on Yahoo! around tech stocks. One of our most popular areas in Yahoo! Finance are quotes pages. We launched that show knowing there was a huge demand for that kind of content.

What do you see in your data that would surprise the average person who works in media?
People want to consume content for free. While there are some opportunities for Internet companies to charge, for the most part, free is going to prevail. If you try to charge [for text-based content], there's always going to a free alternative, some startup out there, or some mid-level Internet company that is providing that content or content that's similar at no charge to the user.

On the video side, it's very different. There are barriers to entry, and it's expensive to create premium video content. I do think that video providers are in a different arena and can and should consider charging for their content.

Where are the opportunities in this new world for the people who create the content -- writers, photographers, videographers?
We're hiring very selectively. When we go out and hire a new writer, blogger, or editor, we create a model, and we look at the return on the investment that we're going to get. We've done a good job within Yahoo! Sports of hiring a team of incredibly professional and talented writers, editors, and bloggers. And we've been able to do it cost-effectively and bring in a solid return on that investment.

As a result, we're now looking to extend those types of investments into News, Finance, and our Entertainment properties. We're not going to go out and hire 300 writers. We're going to hire a select few writers in each of those verticals to help us produce some compelling content that can help differentiate us and build a unique voice in this super-competitive industry.

What are the attributes you're looking for?
It's voice and perspective. We're trying to differentiate ourselves from what's out there. We want to build a personality and a style and a tone. We want incredibly talented people, but we want people who have a style that's their own.

If you look at what we did within sports, we hired [former Sports Illustrated writer] Michael Silver. He's courageous. He's not afraid to print the facts and write the truth and to say what he thinks. By bringing Mike on, we built up some credibility within sports and the NFL, and we also got access to athletes, coaches, and GMs.

AOL and Yahoo! seem to have almost diametrically opposed content strategies: AOL is focusing on the long tail and Yahoo! is going more for mass audience. Why do you think you're right?
We're very focused on monetization. Long tail content across so many verticals is a challenge because, from what we can tell, from talking to advertisers, it's going to be tough to monetize. You're not going to charge for that content, so you're going to monetize it through display advertising and through creative advertising. And advertisers want their brands associated with premium content. Otherwise, you can go to an ad network.

CEO Carol Bartz just hit her one-year mark. How has Yahoo! Media's world changed as a result of her being there?
She's a big supporter of the media businesses. She's a fan. As a result, she has made very quick decisions to invest in the various verticals.

From my perspective, that's been the most refreshing thing I've noticed: her ability and her desire to move swiftly. In one of my first meetings with her, I sat down and walked her through the Sports business. And she said to me, "OK, got it. What do you need?" And I said, "I need this, this, and this." And she asked me, "If I give you this, this, and this, are you going to maintain your margins, and are you going to continue to produce a profitable business?" And I said, "Yes." And she said, "I'm going to hold you to that," and she authorized me to go ahead and make those investments.

E.B. Boyd is a San Francisco-based freelance writer.

[This interview has been edited for length and clarity.]

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