Herb Kelleher — Challenger Brand Champion

June 20, 2022 | blog | By Mike Sullivan

Photo cred Kent Barker

Great challenger brands don’t become great without leaders who truly understand what it means to be a challenger. Occasionally, those leaders are stoic. But more often than not, they are bigger-than-life visionaries who refuse to play by the rules. Leaders like Steve Jobs. Richard Branson. And our favorite challenger brand leader of all time – Southwest Airlines co-founder Herb Kelleher. No one in the past 100 years has had a better understanding of how to compete as an underdog than Herb. He was a one-of-one. A smart, strategic, irreverent maverick who constantly challenged convention and understood the crucial role culture plays in building an underdog brand. If you’re in the process of building your own challenger brand, this is where you start taking notes.

Beloved leader.

On January 4, 2019, the day after Herb Kelleher passed away, an article ran on Forbes called, “20 Reasons Why Herb Kelleher Was One Of The Most Beloved Leaders Of Our Time.” In it, this is what authors and leadership experts Kevin and Jackie Freiberg said about their longtime friend.

“Herb played the game of life full throttle. One of the most passionate people we have ever known, he had a zest for life, an indefatigable spirit, a contagious sense of humor, a servant’s heart and an intellectual acumen that allowed him to carry on an interesting conversation with anyone, anywhere, about anything. For almost 30 years we’ve been asking, ‘What if you could build a company that is as human as the human beings in it? What if you could create a culture that inspires passionate people to come to work fully awake, fully engaged, firing on all cylinders because they know they are doing epic work?’ Herb did.

The Freibergs didn’t set out to frame Herb as the perfect challenger brand leader. But they did. That’s who Herb Kelleher was.

Herb Kelleher is why Southwest Airlines remains the most inspiring story in aviation since the Wright Brothers.

Even now, his leadership is the north star that makes the brand work. A zest for life. Indomitable spirit. Contagious sense of humor. A servant’s heart. A culture that inspires passionate people.

Sound like a certain airline you know?

The ultimate challenger brand leader.

Building challenger brands takes more than running traps and checking boxes. It takes passionate, visionary leadership. It takes the ability to view current reality and imagine what could be despite the odds. Most of all, it takes understanding of who you are as a brand, and who you’re not. It takes understanding of who you stand for, and that “everyone” is not the answer to that question.

Under Herb’s guidance, Southwest Airlines understood that even when you “democratize the skies” and make air travel affordable for everyone, everyone is not the goal. Kelleher’s now famous “Texas Triangle” on the cocktail napkin focused on people who valued quick travel between Houston, San Antonio, and Dallas without breaking the bank. At the time, the vast majority of airline passengers were business travelers on an expense account and rich people who could afford the airfare. Southwest was for everyone else. Talk about the ultimate challenger brand move.

Herb knew that understanding who his customers were was key to building a successful challenger brand. But he also understood that was only half the equation. The more important half was building a culture of service for the brand by employing, training and, yes, loving the people who would embrace it.

“I’d rather have a company bound by love than a company bound by fear.” – Herb Kelleher

The loving leader.

Herb Kelleher believed in the power of culture and more importantly, how to build it among his employees. It wasn’t a top-down edict that demanded buy in. It was an employee-first, customers second mindset that welcomed ideas from anywhere, no matter your title or position. A culture where the CEO listened first and talked second. Where it wasn’t just okay to have fun at work. It was encouraged. Herb understood his people were the key to Southwest’s success, not him.

The results? When he needed the flight attendants to help clean the planes between flights to increase turn time – something flight attendants didn’t do on other airlines – they did it. In 1995, when Herb was negotiating with the Pilots Union, he looked at the stock options the pilots were asking for and suggested they were asking for too little. Wherever the deal ended, he wanted everyone to feel good about it. And when the pilots agreed to freeze their salaries, Herb said, “what’s good for you is good for me as well,” and froze his, too.

Herb Kelleher was the CEO of a $35 billion airline he built from three planes, but he didn’t always act like it. Herb took the offices without a window. He helped load bags on Thanksgiving and remembered the names of every employee. He treated every employee with the same dignity and respect and encouraged individuality. Herb knew you don’t beat the category leader by trying to be a better version of them. You make your own way. You create a lighthouse identity bright enough for anyone to follow. And you maintain full congruence in what you do and say. Herb knew that if you do that then, long after you’re gone, people will remember what you stood for. Even better, they’ll follow in your footsteps.

Herb in his own words.

“If you create an environment where the people truly participate, you don’t need control. They know what needs to be done and they do it. And the more that people will devote themselves to your cause on a voluntary basis, a willing basis, the fewer hierarchies, and control mechanisms you need.”

“We will hire someone with less experience, less education, and less expertise, than someone who has more of those things and has a rotten attitude. Because we can train people. We can teach people how to lead. We can teach people how to provide customer service. But we can’t change their DNA.”

“Culture is intangible. It’s spiritual. You can’t buy it.”

“Southwest isn’t a ‘this is my job, that’s your job’ kind of company. Being successful is our job, and we’re willing to do whatever it takes to achieve that.”

“The people of Southwest have always been my pride, my joy, and my love. Their indomitable dedication and esprit de corps have taken Southwest from a three-airplane dream to a 500-airplane reality.”

Thanks for showing us the way Herb.

MIKE SULLIVAN is president and CEO at LOOMIS, the country’s leading challenger brand advertising agency and a top Dallas advertising agency for digital, social, mobile and user experience. For more about challenger branding, advertising, and marketing, leadership, culture, and other inspirations that will drive your success, visit our blog BARK! The Voice of the Underdog and catch up on all of our posts.

For more about LOOMIS, or to discuss how we can help your company succeed, CLICK HERE

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Mike Sullivan

President at LOOMIS, the country’s leading challenger brand advertising agency


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