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After spending the mid-1980s racing sailboats semiprofessionally, Bill Lynn began to wonder what to do with the rest of his life.

"I had no intention of getting a job," says Mr. Lynn, who eventually made the rounds of interviews at Boston investment banks and did not like what he saw. "There were people in bull pens making cold calls. I bolted."

He next asked for career advice from his father, Bill Lynn Sr., who was then worldwide media director for Coca-Cola Co. and who has since died. "He said, 'Why not try advertising?' "

More than a decade in media planning later, interrupted by a two-year hiatus when he operated his own sail-making company, Mr. Lynn, 36, is Hill, Holliday Advertising's lead global technology media strategist.

In addition to overseeing off-line and online media planning efforts for such clients as Great Plains Software, Fargo, N.D., he is also the lead media strategist for the agency's biggest client, crosstown financial services behemoth Fidelity Investments.

Mr. Lynn, who holds a degree in economics from Tufts University, says one of his biggest challenges of late is figuring out how to best integrate his clients' advertising efforts across the array of ad media offered by today's media conglomerates.

"Media companies are merging at a rapid rate," Mr. Lynn says. "Very rarely are you talking to a [media company] about only one property--say, print. Now, we're talking about [a multitude of] corporate capabilities."

Successful b-to-b media planning, whether aimed at financial services or high-tech audiences, hinges on an understanding that executives often do not see as many media offerings as the typical consumer, Mr. Lynn says. Another key for b-to-b media planning success is taking chances on outlets that might not, at first glance, seem right for reaching an executive audience.

For example, Mr. Lynn recently was given the job of boosting recognition for Sunnyvale, Calif.-based Advanced Micro Devices Corp.'s chips among a b-to-b and retail audience. He bet that users who would choose an AMD chip over an Intel Corp. chip would consider themselves iconoclasts, so he placed AMD's ads in non-conformist magazines, including Outside and Rolling Stone. As a result, he says, recognition of AMD's chips went up "big time" in fourth-quarter 1998.

Mr. Lynn spent his early years in media planning at Grey Advertising, New York, where he worked on accounts such as Orlando, Fla.-based Red Lobster and Kraft USA, Glenview, Ill. He joined Hill, Holliday in 1995 in part because he saw greater technology and interactive media planning opportunities there.

Still, his job requires as much intuition as it does a grounding in hard demographics, Mr. Lynn says. "Somebody [recently] asked me what the major thing was to be good at media planning. You have to be a student of human nature to do

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