All Things Digital

In what is both a surprising and not-so-surprising move, Yahoo has replaced its top U.S. ad sales exec with one from Microsoft.

The departure of Dave Karnstedt, who took over last year when longtime Yahoo ad sales exec Wenda Millard left Yahoo in the first of many controversial partings, has been long rumored internally.

(In fact, I have driven one of Yahoo’s PR people crazy in recent months trying to verify a persistent tip I had been getting that he was headed out the door.)

Karnstedt will be joining Redpoint Ventures, a Silicon Valley venture firm, as an executive-in-residence.

And, in a rejiggering and addition of duties at Yahoo (YHOO), Karnstedt’s job and more is going to Joanne Bradford (pictured here), a longtime and well-known Microsoft (MSFT) exec who decamped from the software giant to helm national ad sales at trendy ad services start-up Spot Runner just six months ago.

There have been rumors swirling that Bradford was unhappy at the smaller company after working at the giant Microsoft.

She was EVP of National Marketing Services, focused on national advertisers, for Spot Runner, joining in a high-profile move in March. Previous to Spot Runner, Bradford was a VP and chief media officer of MSN Media Network, and had worked at BusinessWeek before that.

In any case, the move will be seen as a blow to Spot Runner, which recently did some unusual layoffs, despite receiving a large slug of cash from investors.

(Here is a post and video I did on a recent trip to Spot Runner, including an interview with its CEO Nick Grouf.)

“I am going back to my entrepreneurial, build-something roots,” Bradford told me at the time she joined Spot Runner. “There is such inefficiency in buying and selling of advertising and someone has to solve that, both for big companies and small ones.”

Well, welcome to Yahoo, Joanne, which could use a little efficiency in its buying and selling of ad sales!

Seriously, Bradford will now will take over as SVP of U.S. revenue and market development at Yahoo at a very dicey time.

Besides facing a withering U.S. economy, a weakened stock price after the takeover attempt by Microsoft and ensuing mess related to it, it was revealed that the Justice Department might block the deal Yahoo recently struck to outsource some of its ad sales to Google (GOOG).

Yahoo said that in this newly created role Bradford will oversee sales, market development for advertisers, small business and HotJobs. She will report to Hilary Schneider, EVP of Yahoo’s U.S unit.

Karnstedt, whom I interviewed when he first took over ad sales a little more than a year ago, is leaving to pursue other opportunities.

In Silicon Valley, that means the inevitable stop at a VC firm. Hence, Redpoint!

Interestingly, he joins former Ask.com head Jim Lanzone at Redpoint, while former Yahoo execs Jeff Weiner (Accel Partners and Benchmark Capital) and David Goldberg (Benchmark) also landed cushy EIR gigs after leaving Yahoo.

Karnstedt had been SVP of U.S. sales at Yahoo and had apparently resigned from the company earlier this summer (thanks for not confirming that when I asked so many times, Yahoo!)

With Yahoo seven years, he was charged with the difficult task of integrating Yahoo’s search, display, Blue Lithium and Right Media sales teams.

And while Karnstedt was well liked, many complained that the longtime online ad techie was not enough of a gregarious and schmoozy ad sales exec, with deep relationships on Madison Avenue, as Millard–and Bradford–surely are.

As I wrote in Aug. 2007, after an interview with him at Yahoo’s New York offices:

I made the point to Dave (he is the kind of guy you can call Dave, as you can see pictured here) that an ad guy needs to sell himself, but to no avail, so we press on in text. Nonetheless, let me set the visual scene:

Nicest guy you ever want to meet walks into nondescript room, wearing khaki-oxford-jacket Internet uniform 101. Declares Yahoo is going to kick some advertising butt in the nicest possible way. It is revealed this nice guy has been around the Web block for quite a while. Much chitter-chatter ensues. Cut to my clear-as-Fiji-water observation that nice guy, as nice as he is, has his work cut out for him.”

And now, more than ever in Yahoo’s key ad market, so does Bradford.

After BoomTown broke the news yesterday that top Google exec Sheryl Sandberg was tapped by Facebook Founder Mark Zuckerberg to be COO of the hot social-networking company, I talked with her and got the usual blah-blah quotes about scaling and growing operations and building a platform and how she wasn’t leaving Google as much as “going to an opportunity.”

But, as loyal readers will find out in the weeks and months ahead, she is sure to make for a much more lively new character in our ongoing and near-obsessive coverage of the Facebook saga, which we at BoomTown HQ like to call “As the SuperPoke Turns.”

It is certainly an interesting bet for Sandberg to make the move from the powerful Google (GOOG) to the upstart Facebook. And whether she wins or loses, it will be fascinating to watch.

But fried as she was late last night when we talked after the big announcement was finally made and deserving of a break, BoomTown will bring you a sassier sit-down with Sandberg after she clears out of the Googleplex Friday after six years (wherein all her rights to unlimited visits to the organic soba latte barista and shiatsu massage therapist will be suspended tout de suite!).

So until then, here are some sizzling tidbits about Sandberg (pictured here, with those soon-to-vanish colored Google exercise balls) to chew on:

The 2007 holiday party where Sandberg met Zuckerberg for the first time was thrown by former Yahoo president and COO Dan Rosensweig, who is close to both (apparently, BoomTown’s invite, where I could have witnessed this historic meeting, was lost in the mail!). Interestingly, Rosensweig himself was someone Zuckerberg probably considered bringing into Facebook.

One plus for the socially awkward Zuckerberg is that Sandberg–who spent her formative years swimming in the shark-infested waters of Washington, D.C., as chief of staff to Treasury Secretary Larry Summers during the Clinton administration–has struck a lot of friendships around the Valley. That includes Google rival Yahoo (YHOO), where her husband David Goldberg once headed up the music efforts. Yahoo President Sue Decker is a good friend, for example.

Sandberg even seems to make nice with VCs (she has to, as her husband is now an entrepreneur-in-residence at Benchmark Partners). According to Facebook board member and major investor Jim Breyer of Accel, for example: “I met her in 2001 at the U2 Concert in San Jose. Bono called her name out in front of the whole crowd thanking her for the work she had done with Larry Summers. We (including Bono) all went out for drinks afterwards. Little did I know that it would be a 23-year-old entrepreneur who would finally allow me to recruit her.”

Ah, the sweet ironies of the Valley!

Speaking of which, here’s a video I did in June, with a longish chat with the then-pregnant Sandberg at the start, where we talk about the status of women–or lack thereof–in Silicon Valley.

The occasion was one of Sandberg’s regular gatherings, which she organizes at her home in Atherton, Calif., and which she calls “Women of Silicon Valley.” (Alternatively, BoomTown has dubbed them “ladyfests.”)

The events feature a wide range of speakers, talking to a broad swath of typically high-ranking women technology executives from Internet, software and hardware companies, as well as from other walks of life, about a range of issues. This one was with political pundit and Web diva Arianna Huffington.

Please see this disclosure related to me and Google.

Yet another departed Yahoo executive has landed at a well-known venture capital firm–this time with its former music head David Goldberg’s new stint as an entrepreneur-in-residence at Benchmark Capital. Earlier this week, Andrew Braccia, Yahoo’s vice president for consumer Web search, left the company to become a principal at Accel Partners.

The warm embrace of a plush VC office has always been an attractive option for entrepreneurs, either permanently or in the kind of deal Goldberg has, where he can ruminate on his next move in comfort. In an email he sent around yesterday, he wrote, “I will be looking at opportunities in consumer media and assisting Benchmark portfolio companies.”

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