Selling Like A Mad Man

In this age of programmatic ad buys and self-serve platforms, one of the most overlooked leadership skills in business today is the ability to sell something. Fifty years ago, all of the great ad agencies were built this way, with CEOs like David Ogilvy landing clients on the basis of his wit, charm and “soft sell” salesmanship. Before getting into advertising, Ogilvy was, among other things, a door-to-door stove salesman.

“The experience of door-to-door selling turned Ogilvy into a salesman,” Kenneth Roman wrote in his book “The King of Madison Avenue.”

Salesmanship remains an essential skill for today’s CEOs. Tech titans like Larry Ellison of Oracle and Marc Benioff of Salesforce have built empires based on their personalities and showmanship. Steve Jobs was infamous — and today is greatly missed — for his ability to market the hell out of Apple’s products.

As a startup CEO, I have many responsibilities — everything from managing our product roadmap to marketing and recruiting. As our company grows, some of these responsibilities will fall to others. Delegation should be the goal of anyone who wants to build a significant company. But one role that I will never completely delegate is “Chief Salesperson.” I expect that I will always be leading the charge, helping my company to sell our product in whatever way I can. Here’s why:



Skills. Every CEO must become an effective marketer of his or her company. Getting in front of prospects and customers sharpens presentation skills and increases confidence. Even shy guys like Facebook’s CEO Mark Zuckerberg have learned how to become useful representatives of their company.

Product. There’s no better way to discover the weaknesses of your product than being told firsthand by a potential customer that you don’t measure up. If that doesn’t light a fire under your ass to fix things, nothing will!

Support. Some deals require that CEOs get their hands dirty. A call or in-person meeting can be the difference between closing a deal or having it stuck in the pipeline forever.

Market knowledge. Meeting with actual customers is the best market research a CEO will ever get. The media and technology industry changes so fast that customer meetings serve as an essential way to keep up.

Winning. For my money, there’s still no bigger thrill in business than pitching to and landing new clients. Selling something means that you’ve validated everything that your company stands for.

What was true for David Ogilvy a half century ago is still true today: Truly great CEOs are inspirational leaders who can roll up their sleeves and sell something.

2 comments about "Selling Like A Mad Man".
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  1. Max Kalehoff from MAK, August 12, 2013 at 9:11 a.m.

    Good points. Everyone in the company should be selling! There is a balance, though. A hard-charging sales culture, particularly in a SaaS business, can sell too fast, ahead the company's product-to-market fit. If you scale up sales and customers churn out six-month into the customer life cycle, the bottom will fall out of your business. This balance is particularly hard to balance in a VC-backed company where pressure for new revenues and top-line growth are HIGH.

  2. Al DiGuido from Optimus Publishing, August 12, 2013 at 2:51 p.m.

    Matt...AMEN...You are totally on target...CEO's need to be the company's chief "revenue" officer and sales evangelist. I have seen enough spreadsheet jockys and CEO's who spend alot of time doing personal and industry networking. You need to wake up every day...with a passion towards selling and growing revenue and profits for your company. If this isn't your are in the wrong job. Too many companies are being run by technology and financial leaders these days. Without the sales vision and marketing chops...these companies will not achieve the leadership available in their respective markets. I will go one step further...a CEO with a sales mindset will imbue in ALL employees that irrespective of their title and function, they are all responsible for "selling" the value of the company to those who may express a need in your product and/or service.

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