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The Sales Trek

Everyone starts somewhere, so the saying goes. But in the highly competitive world of sales, where successful professionals don multiple hats and deploy innumerable skills, the end point is frequently…open-ended. Which is apparent with these five go-getters, each at the top of their game in wildly divergent industries. However, they all share the distinction of having started in sales. Here, below, the craziest, most inspiring sales trajectory stories so far.

Howard Schultz

Industry: Food/Beverage

Company: Starbucks

Sales Position: Began by cold-calling at Xerox, selling word processors. He then joined Hammarplast as an appliance salesman and worked his way up to director of sales.

When: 1980s

Net Worth: $2.6 billion

HOWARD SHULTZ bought Starbucks in the 1980s and made it into one of the world’s top brands, as we know it today. He was the CEO of the company from 1986 to 2000 and again from 2008 to 2017. Shultz expanded the company from 11 stores to more than 28,000 worldwide. Before those grand achievements, Shultz got his start by selling word processors via cold-calling at Xerox. He then joined Hammarplast as an appliance salesman and worked his way up to director of sales, which led him to discover Starbucks Coffee, Tea and Spice Company. You know how it goes from there.

Kanye West

Industry: Entertainment/Clothing

Company: GOOD Music, creative content company DONDA, Yeezy

Sales Position: Sales assistant, Gap

When: 1990s

Net Worth: $160 million

KANYE WEST is a critically acclaimed rapper, songwriter, producer, entrepreneur and fashion designer — not to mention one of the world’s greatest provocateurs. But before he was Ye, West was a sales assistant at a Gap clothing branch in Chicago. Now considered a fashion icon for his personal style and clothing lines, most notably the Yeezy collaboration with Adidas, Kanye credits the clothier with inspiring his addiction to style. He’s mentioned his sales role at the clothing chain in several songs and interviews, including one in which he expressed the desire to take over creative control of the Gap one day. He has even said he would like to be “the Steve Jobs of the Gap.”

Warren Buffett

Industry: Conglomerate

Company: Berkshire Hathaway

Sales Position: Securities salesman

When: 1950s

Net Worth: $81.4 billion

WARREN BUFFETT has been one of the top five richest people in the world for the past two decades. He is the chairman, CEO and largest shareholder of Berkshire Hathaway. But before the wealth and fame, he was a securities salesman for three years at Buffett-Falk & Company in the 1950s. In fact, even as a kid, Buffett published a horse-racing tip sheet and hawked newspapers and pinball machines. That knack for business and sales inevitably led to his greatest successes — including ownership of some of the very papers he once sold.

Meg Whitman

Industry: Technology

Company: Previously CEO of eBay and HP

Sales Position: Sold ads for a magazine

When: 1970s

Net Worth: $3.2 billion

In 2014, Forbes named MEG WHITMAN 20th in its list of the World’s 100 Most Powerful Women. The New York Times has cited her among the women most likely to become the first female President of the United States. The chief executive officer of eBay from 1998 to 2008, she oversaw its expansion from 30 employees to 15,000 while boosting revenue from $4 million to $8 billion over the same period. She also has served as an executive of Hewlett Packard, Disney, DreamWorks, Procter & Gamble and Hasbro. Prior to her immense success, however, Whitman sold advertisements for a local magazine while she attended Princeton University. It was this first job in sales that led her to pursue a degree in economics and eventually a mega-successful career in business.

Ginni Rometty

Industry: Technology/Cloud Computing

Company: President and CEO, IBM

Sales Position: Worked in sales at IBM, worked her way up to SVP of Global Sales in 2009

When: 1990s–2000s

Net Worth: $45 million

GINNI ROMETTY became president and CEO of IBM in January 2012. She is a 36-year veteran of the iconic technology company and has led IBM’s transformation into a data company, pushing its cloud and analytics products. She first joined the company as a systems engineer in 1981 and spent the 1990s working her way up the ladder, eventually serving as head of sales. Four years later, she became CEO.

Brian Taylor Illustration

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