The Career Path to Becoming a Retail Rock Star CEO

Illustration of one person running up stairs to the top and another hopping to the top

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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 anymore. 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.

There are 4 different career paths to look at:

  1. Traditional rise through the ranks
  2. Company and industry hopping 
  3. Specialized focus and expertise
  4. Retail Enterprenuerialship

Traditional Rise Through the Retail Store 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.

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

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

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

Company-hopping, Industry-jumping Career Path

In direct contrast to the traditional rise through the ranks is the career path in which the CEOs hopped, jumped and zig-zagged their way to the top of a retail organization. These leaders moved with ease between different companies and different industries, rising a little higher with each move until they leapfrogged to the top of a major retail operation.

This is more common for contemporary CEOs, which gives the impression that today’s retail organizations are less about grooming and more about snatching up the already groomed.

Even though industry jumping is commonplace, retail leaders and analysts are still somewhat shocked when a retail organization appoints a CEO who has no prior retail experience. This was the case with eBay’s Meg Whitman, and both of Home Depot’s last two CEOs, Robert Nardelli and Frank Blake. Whitman had neither technical nor retail experience when she was recruited to lead eBay out of relative obscurity.

Nardelli had experience in manufacturing giant, General Electric, and Blake had mostly government experience before they each took over the helm of Home Depot. The zigzag career paths of these three chiefs illustrate how the company-hopping, industry-jumping career path can work.

Margaret (Meg) Whitman, CEO, eBay, 1998-2008

  • Born in Long Island, NY
  • Graduated from Cold Spring Harbor High School, Cold Spring Harbor, NY
  • B.A. degree in Economics, Princeton University
  • Advertising sales, Princeton undergraduate magazine
  • M.B.A. degree, Harvard Business School
  • Brand management for Noxzema, Procter & Gamble
  • Consultant, Bain & Company
  • Vice president, Bain & Company
  • Sr. vice president for marketing, consumer products, The Walt Disney Co.
  • President, Stride Rite
  • President and CEO, Florist Transworld Delivery
  • Global management and marketing, Hasbro CEO, eBay

Robert Nardelli, CEO, Home Depot, 2000-2007

  • Born in Old Forge, PA
  • Father was a GE plant manager, mother was a real estate agent
  • Graduated from Rockford Auburn High School, Rockford, IL
  • B.S. degree in business from Western Illinois University, Macomb, IL
  • M.B.A. degree, University of Louisville
  • Entry level manufacturing engineer, General Electric
  • Management, GE Appliances
  • Management, GE Lighting
  • Management, GE Transportation Systems
  • Executive vice president & general manager, J.I.Case Company / Tenneco
  • Executive vice president and CEO, CAMCO
  • President and CEO GE Transportation Systems
  • President and CEO, GE Power Systems
  • Senior vice president, General Electric
  • CEO & Chairman, Home Depot

Specialized Focus and Expertise Career Path

Often retail organizations will choose chief executives who possess expertise in a specific area that is determined to be key to the company’s future. This career path sometimes has an industry-hopping aspect to it, but the jump seems more logical and less shocking to outside observers.

Jeff Bezos had neither retail nor publishing-related experience before he started Amazon, but he had the essential technical expertise to create the infrastructure. H. Lee Scott had a distinct transportation and logistics career path, which was an aspect of the business that Wal-Mart was interested in keeping strong.

Restaurant experience is not what Darden wanted from Clarence Otis when they chose him to be CEO. Darden wanted his finance experience to keep that aspect of its restaurant chains strong. The career paths of these three retail CEOs illustrates that specialized focus and expertise in one aspect of a retail business can eventually lead to the CEO office as well.

H. Lee Scott, CEO, Wal-mart

  • Born in Joplin, MO
  • Son of a gas station manager and an elementary school music teacher
  • Father’s helper, Phillips 66 gas station
  • Graduated from Baxter Springs High School, Baxter Springs, KS
  • B.S. degree in Business, Pittsburg State University in Kansas
  • Executive Development Program, Penn State University
  • Executive Development Program, Columbia University
  • Laborer, tire mold manufacturer
  • Management training program, Yellow Freight
  • Terminal manager, Yellow Freight Systems
  • Assistant director of transportation, Wal-Mart
  • Director of transportation, Wal-Mart
  • Vice president of transportation, Wal-Mart
  • Vice president of distribution, Wal-Mart
  • Senior vice president of logistics, Wal-Mart
  • Executive vice president of logistics, Wal-Mart
  • Executive vice president of merchandise, Wal-Mart
  • President and CEO, Wal-Mart Stores division
  • Vice chairman and COO, Wal-Mart
  • Director of Wal-Mart Stores Inc.
  • President and CEO, Wal-Mart

Clarence Otis, Jr., CEO, Darden Restaurants

  • Born in Vicksburg, MS, grew up in the notorious Watts ghetto in South Los Angeles
  • Son of a janitor
  • Graduated from Jordan High School, Los Angeles, CA
  • Bachelor’s degree in both economics and political science from
  • Williams College, Williamstown, MA (Magna Cum Laude)
  • Law degree, Stanford University Law School
  • Corporate law, specializing in securities law and mergers and acquisitions, Donovan Leisure Newton & Irvine
  • Lawyer, Gordon, Hurwitz, Butowsky, Weitzen, Shalov & Wein
  • Investment banking, Kidder, Peabody & Co.
  • Vice president, First Boston Corporation
  • Managing director, Giebert Municipal Capital
  • Managing director and manager of public finance, Chemical Securities (JP Morgan Securities)
  • Vice president and treasurer, Darden Restaurants
  • Senior vice president of investor relations, Darden Restaurants
  • Senior vice president of finance and treasurer, Darden Restaurants
  • CFO, Darden Restaurants
  • President of Smokey Bones Barbeque & Grill, Darden Restaurants
  • Executive vice president, Darden Restaurants
  • Director, Darden Restaurants
  • CEO, Darden Restaurants

Retail Entrepreneurship Career Path

The only surefire strategy for becoming a retail CEO is to start your own company and award yourself the title. The entrepreneurs are the true creators in the retail industry. They didn’t follow much of a career path at all. Instead, they defined their own career, charted their own destination, and sketched out their own road map. 

Sam Walton of Wal-Mart was an entrepreneur almost from the start. Others, like James Sinegal of Costco, started down a traditional career path and made the entrepreneurial leap in mid-career. The career paths of these two retail legends show that it’s never too early or too late to appoint yourself as your own CEO.

Sam Walton, CEO, Wal-Mart

  • Born in Kingfisher, OK
  • Son of farmers
  • Milked the family cow, bottled the milk and delivered it to customers
  • Newspaper delivery
  • Graduated from Hickman High School in Columbia, MO, (voted “most versatile boy”)
  • Bachelor’s degree in economics, University of Missouri, Columbia, MO
  • Waiter
  • Lifeguard
  • ROTC officer
  • Management trainee, J.C. Penney
  • DuPont munitions plant, Tulsa OK
  • Security supervisor at aircraft plants and POW camps, US Army Intelligence
  • Purchased a Butler Brothers franchise retail store in Newport, AR
  • Purchased another Butler Brothers store in 1950 in Bentonville, AR and called it Walton’s 5&10
  • Sold the Newport Butler Brothers store ($50,000 profit)
  • Purchased a non-franchised retail store in Fayetteville, AR
  • Purchased larger stores and called them Walton’s Family Center
  • Opened the first “Wal-Mart” in 1962
  • Founder and CEO, Wal-Mart

James Sinegal, CEO, Costco

  • Born in Pittsburgh, PA
  • Son of a steelworker
  • Graduated from Helix High School, Pittsburgh, PA
  • A.A. degree, San Diego City College
  • Enrolled in San Diego State University, did not graduate
  • Mattress handler, Fed-Mart Corporation
  • Bagger, Fed-Mart Corporation
  • Store manager, Fed-Mart Corporation
  • Vice president of merchandising and operations, Fed-Mart Corporation
  • Executive Vice President, Fed-Mart Corporation
  • Vice President of Merchandising, Builders Emporium
  • President, Sinegal/Chamberlin & Associates
  • Executive vice president, Price Company
  • Co-founder, president, and CEO, Costco Wholesale

Moving in the Right Direction in Your Retail Career

When 19,000 college graduates were asked by the National Association of Colleges and Employers (NACE) how they would choose a job, the class of 2008 respondents said their highest priority was finding a company that “provides the opportunity for advancement.”

For those who want the highest possible advancement to the ultimate retail destination, the career paths of contemporary CEOs can serve as inspiration that many different routes are available. The journey will be easiest for those who are the most flexible, adaptable, and resourceful, especially when the next steps are not very clear. If you’re not exactly sure how you’ll “get there from here,” take a step that provides some type of learning or expansion. That’s one step that all rock star CEOs found to be a step in the right direction.