CEOs

So, You're in Sales But (Secretly) Yearn to be a CEO. Here's How to Make That Happen.

For starters, you're in good company: Warren Buffett, Mark Cuban and Howard Schultz all started in sales.
So, You're in Sales But (Secretly) Yearn to be a CEO. Here's How to Make That Happen.
Image credit: Angelita Niedziejko | Getty Images
Guest Writer
CEO, Datical
8 min read
Opinions expressed by Entrepreneur contributors are their own.

Warren Buffett. Mark Cuban. Howard Schultz: Besides being among the richest men in the world, all are members of another rare club: successful CEOs who started out as salespeople.

Related: 3 Things to Do If You Want to Become a CEO by Age 30

The young Buffett sold securities for three years. Cuban was a sales rep who taught himself programming. And Schultz sold copiers at Xerox.

In the tech industry, just 8 percent of CEOs at the largest 100 U.S. firms have primary backgrounds in sales, and less than 30 percent have any sales experience at all, according to a 2017 study by the Korn Ferry Institute. The vast majority of people who ascend to CEO headed large divisions or were chief operating officers. In Silicon Valley and other tech hubs, engineering backgrounds also are common.

But, as someone who himself spent 12 years in sales before becoming a CEO in 2015, I understand why so few chief executives come from the sales ranks. Most people who build a career in sales simply love selling, and often lack a desire to move into management tracks that could lead to the corner office. I remember the sales colleague who arched his eyebrows when I first took a management position. "Why are you doing that?" he asked.

That kind of attitude is a shame because I think many salespeople have what it takes to be great CEOs. Many possess the same skills that are essential to leading a company: communications, strategic thinking, ambition, integrity, passion for the business and, last but not least, keen perception of customer needs.

As the Korn Ferry report put it: "While uncommon, technology CEOs who come up through sales bring with them valuable knowledge and expertise. Many of the traits that it takes to be a successful sales executive are also those that make for a successful tech CEO. Sales leaders that make the effort to broaden their backgrounds can distinguish themselves as prime CEO candidates."

You could have been a contender. You still could be.

I wish companies would do a better job identifying leadership potential within the sales force. I wish more salespeople would recognize and nurture their own capacity for higher cross-company roles.

And I haven't given up on those things happening: Here are five pieces of advice I would give to a sales specialist about how to hone his or her leadership abilities, to prepare to be a CEO contender:

1. Develop cross-organizational empathy.

Sales is intensely motivated by one primary driver: closing deals. But sales is hardly one-dimensional; though singular in focus, it requires a complex palette of skills.

Related: The Route to Becoming CEO Depends on Where You Live

The best sales teams also understand the importance of customer success, but their job goes beyond that. Any sales leader with CEO aspirations must step outside of that box and begin to empathize with and understand other parts of the business -- the developers, marketing, HR, etc. How does each work? How is each motivated to achieve success? How does each each align to meet broader company goals?

These are strategic questions a would-be CEO must learn to ask. He or she also must communicate effectively with many different audiences.

How do you get there? As a salesperson at a large tech company, I took on stretch assignments -- participating in a task force on competitive intelligence and joining a group that re-designed the company website. (The latter was a miserable experience, but I learned a lot!) Any opportunity that helps you learn about other parts of the business is a good one.

If you're working on a transition to CEO, you'd also be wise to find a mentor who is a CEO, ideally one who didn't come from a sales background. Find out how this person works, and worries about, the problems that need to be solved. You can learn a ton from these people, with the side benefit being that you'll expand your network.

2. Appreciate that hiring well is job No. 1.

When you're in sales, you hire for one type of role: people who can sell or can manage salespeople. But CEOs hire the most important functional leaders: the CMO, CFO, head of product development, etc.

A salesperson transitioning to CEO must recognize that building a great team is one of the most crucial aspects of the position. This again is why cross-organizational empathy is so important. You need a deep grasp of each department's mission and who the best people are to lead it.

"I have a technical degree as an engineer, but spent the first 20 years of my career driving revenue through sales and sales leadership roles," Chris Cook, president and CEO of Delphix, shared with me. "In 2006, when Wily Technology was acquired by CA, I became a general manager and had engineering, product management and marketing for the first time. Even during my time in sales, I was always close to the engineers and developers, and had an affinity to that part of the business.

Once he mastered those departments, Cook added, "I jumped in with both feet and absolutely loved the product side of the business." For ten years, he's focused on product and the people who build it, "to gain a broad perspective for all elements of a software company, and how the various piece parts fit together most effectively."

3. Sharpen your finance knowledge.

Strong comprehension of financial operations is de rigueur for a CEO. About 30 percent of Fortune 500 CEOs spent the first few years of their careers developing a strong foundation in finance, according to a study by consulting firm Heidrick & Struggles.

Because finance is a common experience for so many CEOs, a lack of this skill set could be a stumbling block. Salespeople with CEO aspirations should keep this in mind as they move to other corporate positions and assignments.

4. Recognize that "company culture" is more than a buzzword -- it matters.

Company culture has become more important than ever, and not just for the usual reasons that culture sets the company's values and identity.

Having a strong, positive culture is also often a differentiator in recruiting and retaining the best people in a competitive labor market, and in nourishing corporate reputations in the age of social media. Fostering a healthy culture in the sales organization as head of sales is one thing; doing it companywide is another. This is where salespeople need to think beyond quotas and numbers.

"Having directly led a sales force, I know first-hand there comes with it a unique culture that can't be found elsewhere. That sales spirit is an important piece in the overall corporate culture," Phillip Braithwaite, president and CEO of Hart InterCivic, told me. "When I stepped into the chief executive role in 2011, I was more connected to all facets of the company and saw for the first time how important it was to have a shared sense of purpose and identity that resonated across the entire organization."

5. Don't micromanage sales.

CEOs who come from sales have to hire a really good VP of sales and let that person do the job. It's so tempting to be a control freak in terms of the area you know best, but all that will do is distract you from the myriad other CEO responsibilities and burn out your sales leader.

So, you should re-train your brain and pay equal attention to all the parts of the business.

Derek Langone, CEO of XebiaLabs, echoed a similar sentiment, telling me, "As a sales leader, I was always interested in company success, but I measured it exclusively by sales results. As I matured, I realized how all the functional areas of the company contribute to, and are required for, overall success.

"However, as a company grows, the swim lanes between departments become more and more defined. As a CEO, I deal with that by using many of the same management approaches that allowed me to be an effective sales leader, but on a broader scale. For example, in many cases, I'm still the dot connector for the organization and the market, just as I was in sales, but my role is now much more visible and more representative of the entire company.

"There is certainly a learning curve, but I feel strongly that the skills learned as a sales leader are quite transferrable to the CEO function."

Related: Slicing and Dicing My Way to Becoming an Entrepreneur

To salespeople who believe they have the right stuff for CEO, I say: You can make it happen. If you're interested in and are up for the challenge of being responsible for different parts of the business, it comes down to desire.

Can you do it? Are you motivated to do it? Is it the right fit?

If the answers are yes and you're willing to do the necessary groundwork, you can make the leap.

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