8 CEOs who were once sales reps

This is not a motivational piece that goes, “Every salesperson today can be a CEO tomorrow.”

But if you’re a salesperson today, and you have the drive to learn more, the will to work hard, and the tenacity to move past failures, this post will tell you that becoming a CEO is not impossible.

Because it’s already been done by at least 8 others.

Which is why this blog is a collection of stories. About people who worked as sales reps early in their career, rose through the ranks — and sometimes switched industries — before stepping into the corner office.

  1. Samuel Palmisano

When you join an organisation like IBM, especially as a sales rep in 1973, you’re content with keeping your job and coasting through life. But Samuel Palmisano was made of sterner stuff. Part of a team entrusted with selling AS/400, IBM’s new computer, Sam reached out to software companies and convinced them to write programs for the computer before it entered the market. It was a unique initiative, and it paid off. Even as the AS/400 went on sale, customers had 1,000+ programs to choose from, making the computer one of the most profitable products in the company’s history. From there, Sam only went upwards, and served as CEO between 2002 and 2011. IBM was the largest IT company in the world as of 2009.

2. Warren Buffett

You know him as the world’s richest person in 2008, and one of the top 5 richest people in the world over the last 2 decades. But did you know that Warren sold securities at Buffett-Falk & Company for three years in the 1950s? Even before that stint, Warren had a history of selling: he sold his own horse-racing tip sheet, was a paperboy, and even made profits by installing pinballs in barbershops. Using his tactical acumen for investments, he bought shares and eventually gained control of Berkshire Hathaway, a textile company in the 1960s. He became Chairman and CEO in 1970, and expanded the company by adding assets in media, insurance, oil, and soft drinks. As of 2016, Berkshire Hathaway has a revenue of $223.6 billion.

3. John Paul DeJoria

When John Paul DeJoria completed his service in the US Navy in 1964, he didn’t have a regular job, and he didn’t have the money to go to college. He became a salesman for Collier’s Encyclopedia, and received the Man of the Year award in 1966 for being their top salesman. He embarked on a series of jobs selling hair care products for various companies, but kept getting fired because he wasn’t the socializing type. So in 1980, he and his friend Paul Mitchell started their own company, with $700 and three products (two shampoos and a conditioner). His door-to-door selling experience came in handy, and the company became John Paul Mitchell Systems, the producer of the Paul Mitchell line of professional hair care products. The company now has an estimated $1 billion in annual sales. DeJoria is estimated to be worth over $4 billion, thanks to another successful business: Patrón Spirits Company, which produces and sells premium tequila.

4. Anne Mulcahy

Joining Xerox as a field sales rep in 1976, Anne gradually worked her way up the corporate ladder, moving into senior sales positions and even serving as VP of HR in the mid-90s. She became CEO of Xerox in 2001 when it was on the verge of bankruptcy; stocks further fell 15% after her appointment. But she set off on a 90-day tour to Xerox’s offices, where she harnessed her sales experience by listening to customers and figuring out what was wrong at the company. She also gained the trust of her employees by being honest, hardworking, firm and fair. Through a series of strategic and bold decisions, by 2004, the printing giant was back on the road to profitability.

5. Robert Herjavec

Robert sold IBM mainframe emulation boards for a company called Logiquest, which gave him the experience to start his first tech company, BRAK Systems. He sold it to AT&T for $30.2 million in 2000. After negotiating the sale of another IT company to Nokia for $225 million, Herjavec retired briefly, and returned with his own company, The Herjavec Group. The company is now Canada’s largest IT security provider, and is at #2 on Cybersecurity 500, a list of global companies providing cybersecurity solutions and services.

6. Howard Schultz

Howard started his career by cold-calling at Xerox, selling word processors. He then joined Hammarplast as an appliance salesman. Hammarplast sold European coffee-makers in the United States. When Howard became Director of Sales in the 1980s, he observed that more coffee makers were being sold to a small store in Seattle than to Macy’s. He visited the store — then called Starbucks Coffee Tea and Spice Company — and its homely feel fascinated him. He joined them as their Director of Marketing, and on a business visit to Milan, realized that cafés inspired a sense of community — they were more than just restaurants. He wanted to infuse that spirit into the American culture, despite the fact that coffee consumption in the US was on the decline. He eventually bought Starbucks in 1987 and became its CEO. In 2015, Starbucks’ revenue was $19.16 billion.

7. William C. Weldon

In 1971, after graduating in biology, William Weldon attended an interview and made an impromptu sales pitch for a ballpoint pen. It earned him the job of a sales rep at Johnson & Johnson, in their McNeil Pharmaceuticals division. As he assumed manager and VP roles, in 1995 he became the president of a new unit that focused on tools for endoscopic surgery. By 1996, Weldon had ensured that sales were exceeding those of the previous tools company. He soon got managers from sales and marketing to work alongside research scientists and R&D executives to decide what drugs should be made. In 2002, he became the CEO. He retired in 2012, after 41 years at the company.

8. Mark Cuban

A sales rep who taught himself programming? Not a myth if you know Mark Cuban. Starting off by selling software, Mark started a company called MicroSolutions, grew it to $30 million, and sold it to CompuServe. Along with partner Todd Wagner, he started internet radio company AudioNet, which became the video portal Broadcast.com, and sold it to Yahoo for $5.7 billion in 1999. He even acquired the Dallas Mavericks and inspired them to a title win in 2011. Mark is now the chairman and CEO of AXS TV. As a successful entrepreneur, he is also a judge on Shark Tank, ABC’s popular reality TV show where aspiring entrepreneurs pitch to a panel of “shark” investors.


In a Gallup poll, car and insurance salespeople were among the three least trusted professionals in the United States.

But according to another Heidrick & Struggles survey, nearly 20% of Fortune 500 CEOs started out in sales and marketing.

Salespeople are often seen as smooth talkers, and everyone — from the common man to Steve Jobs — has an opinion against them. But you cannot discount their strengths: a flair for communication, an action-oriented approach, and the ability to strike an instant connection.

Which, by the way, are also the traits of a successful CEO.


Know other CEOs who started in sales? Tell us in the Comments.

If you’re a salesperson and looking to quickly move up the corporate ladder, it’s perhaps time you invest in CRM software to help you. Start optimizing your sales pipelines, monitor your revenue streams, create sales reports that can easily be consumed and be on your way to becoming the next CEO!

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