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The Career Path to Becoming a Retail Rock Star CEO


It’s hard to pinpoint when or why it began, but these days the CEOs of America’s best known companies have attained a fame that rivals that of professional athletes and rock stars. High profile corporate leaders are being idolized, scrutinized, and televised. With salaries, bonuses, and exit packages that rival those of America’s best known celebrities, the position of corporate CEO has gained more than a little sex appeal.


While many employees in the retail industry today have their eye on the seemingly glamorous chief executive job, the goal seems distant and somewhat unattainable. There are plenty of great musicians who never make a platinum record. There are also plenty of brilliant employees who will never attain rock star CEO status. As the lines between business and celebrity start to blur, retail employees are left wondering if progressive career paths still exist or if, like rock stars, they’re going to have to hope for a “big break” to make it to the top of the retail industry.

Famous CEOs Leave Clues for Career Advancement

Today’s ascent up the retail corporate ladder is less like a singular climb up a sturdy structure and more like a blind and crowded crawl around an unmarked labyrinth with shifting walls. Well-established and fixed hierarchies have given way to constant shuffles of the org chart boxes. Just when you think you have your next move mapped out, some overpaid OD consultant swoops in and changes the topography. It’s like a bad road trip in the family SUV. You can see where you want to go, but you can’t find a way to get there from here.

There are very few companies that will take employees by the hand and lead them through their career journey any more. Employees today are left to use their own navigational skills to make their way to the penthouse office suite. It may be a mysterious journey, but it’s not an impossible one. By reconstructing the professional route that some well-known CEOs took to get to the top, certain similarities and patterns emerge. A single executive’s work history may not mapquest the most relevant career path for contemporary corporate America, but each path can provide clues to those retail employees who are looking for career advancement direction.

Traditional Rise Through the Retail Ranks

Progressive promotion is the old school strategy for success in the retail field. Work hard, be loyal, and grow with the company. This career path is slow, it’s steady, and it’s definitely not glamorous, but it is a practical path to take. While rising through the ranks might have been considered the only way to advance for baby boomers, it’s a relatively uncommon phenomenon for today’s retail chief executives. Nevertheless, the career paths of Target’s Robert Ulrich, Best Buy’s Brad Anderson, and Walgreens’ Jeffrey Rein stand out as classic examples of a good, old-fashioned ladder-climbing ascent.

The Career Path of Robert Ulrich, CEO, Target Corporation, 1994-2008

  • Born in Minneapolis, MN
  • Son of a 3M executive
  • B.A. degree, University of Minnesota
  • Stanford Executive Program, Stanford University Graduate School of Business
  • Cart attendant, Dayton Hudson Corporation
  • Merchandising trainee, Dayton Corporation
  • Sales manager, Dayton Corporation
  • Buyer, Dayton Corporation
  • Group manager, Dayton Corporation
  • Divisional merchandise manager, Dayton Corporation
  • Merchandising, Dayton Department Stores
  • Vice president and general merchandise manager Dayton’s Department Stores
  • Senior vice president of stores, Dayton’s Department Stores
  • Executive vice president for merchandise, sales promotion, and presentation, Dayton’s Department Stores
  • President and CEO, Diamond’s Department Stores
  • Co-president, responsible for merchandising, marketing, and distribution, Dayton Hudson Department Store Group
  • President, Target Stores
  • Chairman and CEO, Target Stores


The Career Path of Brad Anderson, CEO, Best Buy

  • Born in Sheridan, WY
  • Son of a Lutheran minister
  • Below average high school student
  • A.A. degree, Waldorf College
  • B.A. degree in sociology, University of Denver
  • Attended Northwestern Seminary, St. Paul, Minnesota
  • Commissioned salesman, Sound of Music stereo
  • Store manager, Sound of Music
  • Sales manager, Sound of Music
  • Vice president, Best Buy
  • Executive vice president, Best Buy
  • Board of directors, Best Buy
  • President and COO, Best Buy
  • CEO, Best Buy


The Career Path of Jeffrey Rein, CEO, Walgreens

  • Born in New Orleans, LA
  • Graduated from Sahuro High School in Tuscon
  • Bachelor’s degree in accounting, University of Arizona, Tuscon
  • Bachelor’s degree in pharmacy, University of Arizona, Tuscon
  • Employee, Defender Drug
  • Pharmacy intern for his future father-in-law
  • Employee, Long’s Drugs
  • Assistant manager, Walgreens
  • Store manager, Walgreens
  • District manager, Walgreens
  • Divisional vice president, Walgreens
  • Vice president of marketing systems and services, Walgreens
  • Treasurer, Walgreens
  • Vice president of marketing systems and services, Walgreens
  • Executive vice president of marketing, Walgreens
  • President and COO, Walgreens
  • CEO, Walgreens
  • Chairman, Walgreens


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