At Yahoo, Bradford has overseen ad sales—and she has deep relationships with advertisers that could help Demand Media persuade them that it’s more than a “content mill” and therefore worthy of their premium ad dollars. Over the last three years, she has held three high-level posts: She was the chief media officer of the MSN Media Network, responsible for its profile in the ad community before leaving that post to join SpotRunner as EVP of national marketing services in March 2008. Then, after only seven months, she took the Yahoo job in late 2008.

Yahoo, meanwhile, is losing Bradford just as it has been doubling down on its pitch to marketers, trying to position itself as an alternative to TV and spending heavily on an ad campaign designed in part to convince advertisers to buy display ads on its sites. By all accounts, Bradford’s departure was completely unexpected.