The 5 Essential Weapons That Help Challenger Brands Win

August 31, 2021 | blog | By Mike Sullivan

Challenger branding is not for the weak of heart. As the country’s leading challenger brand advertising agency for more than 20 years, we’ve had the privilege to work with dozens of challenger brands large and small in every business sector and from every part of the country. Last year, we wrote an entire book on why we love jumping in the trenches with brands that are scrappy and underfed.  For us, there’s nothing more satisfying than helping challenger brands go toe to toe with the category leaders. That’s why every day, we focus on the five essential weapons that help challenger brands win.

In this post, we’re focusing on what it takes for challenger brands to go to war and beat the brands at the top of their category. To fight against the big dogs that have more money, more resources, more people, and more pull — and still win. There’s clearly a lot that goes into that. But from our experience fighting side by side with challenger brands of all types, we know when underdog brands go to war and focus on the five essential weapons that help challenger brands win, anything is possible. 

The 5 C’s of Challenger Brand Warfare.

In The Art of War, legendary Chinese military strategist Sun-Tzu posited that “every battle is won or lost before it is ever fought.” That’s absolutely true in the brand wars. Because, like most battles, the actual fighting is less a harbinger of success than is the preparation, strategy, and mindset of those in the actual fight.

When challenger brands go to war against the category leaders, they do so knowing they are undercapitalized, understaffed, and under the gun. Despite that, many challengers find a way to punch above their weight. They grab market share, and even force big brands into unforced errors. How? They embrace the Five Cs of Challenger Brand Warfare – the five essential weapons that help challenger brands win: Courage, Connection, Creativity, Company Culture, and Change.


In chapter two of The Voice of the Underdog, we note there are three primary factors that distinguish true challenger brands from the leading brands in their categories. Those factors are State of Market, State of Mind, and State of Readiness. While the first two – State of Market (understanding where you stand compared to your competition) and State of Mind (understanding who you are as a company or brand) – are somewhat constant, the third factor, State of Readiness (understanding how ready you are to go to battle) is variable. And it requires extreme Courage, the first C in the essential weapons that help challenger brands win.

There’s nothing easy about fighting forces bigger than you are and for underdog brands, that fight is often a fight for survival.

According to a Harvard University-based project called The Economic Tracker, as of this past June there were 37.5% fewer small businesses open nationwide compared with January 2020. When you’re a challenger brand, courage is a requirement. Courage is what makes you show up for the fight when there are a thousand things that tell you not to. But for those willing to muster it, there’s an infectious energy that flows from courage. It can light up both your team and your customers. As Americans, we love the underdog. Better yet, we champion the ones willing to stand up to those on the pedestal. Having the courage to get in the fight tells the world you will not be overlooked, you will not be underestimated, and you are not invisible. That leads to C number two.


In business, as in relationships, we all crave genuine connection. More often than not, we gravitate toward connecting with those who are most like us. That is crucial for challenger brands and here’s why — the overwhelming majority of us feel like and think of ourselves as underdogs. Because we are. If you’re a challenger brand going to war, there are two connections crucial to your success. First, is the connection you have with your team and their connection to each other. The second, is the connection you build with your customers.

Successful challenger brands are built on the foundation of great company cultures. Fostering meaningful connection throughout your team is imperative. Only when your team is pulling in the same direction can you connect with your customers in a meaningful, consistent way. For underdogs, every relationship is critical. Because every interaction is an opportunity for brand endearment and conversion. Customer touches are not the goal. Authentic, lasting customer connection is the key to sustainable success.


For any challenger brand, creativity can be your greatest weapon. It’s also the quickest way to not just level the playing field but tilt it in your favor. To quote Apple, one of the greatest challenger brands of all time, “thinking differently” isn’t just a requirement for fighting giants. It’s the only hope you have to beat them. Successful challenger brands understand that creativity and great ideas can literally come from anywhere.

Like many advertising agencies, at LOOMIS, we have a creative department that does extraordinary work. But we also realize how myopic and unfair it would be to assume that only our creative team could provide great ideas for our agency and clients. Whether you’re the leader of an advertising agency, marketing firm, or in-house brand team, telling your entire team you expect them to think creatively isn’t a burden. It’s empowerment. Give your team, your company, your agency, even your customers, the permission to deliver great ideas. You’ll have a bounty of ideas to choose from far greater than you could have dreamed. That’s how you compete and win against the category leaders.


As we stated before, truly successful challenger brands are built on the foundation of great company cultures. When you’re an underdog brand, there is no shortage of stormy seas you have to navigate. Having a solid company culture beneath everything you do keeps you and your team above water when things get tough. Without hyperbole, company culture is the most fundamental advantage challenger brands possess. It doesn’t matter how large or small you are in your market. Putting culture first is transformative for any brand that embraces that mindset.

Great company cultures are infectious, and every great employee wants to be a part of one.

You, as a leader, are not scalable. But disseminated through your culture, your leadership is. Build and foster a meaningful, supportive, empowering company culture and you’ve already done something most of your bigger competitors never will.


The fifth and final C in the essential weapons that help challenger brands win is Change. It’s perpetually the one we fight the most. But ironically, without it, underdogs couldn’t succeed no matter how hard they tried. For successful challenger brands, the goal isn’t playing the game better. It’s altering how the game is played. Rewriting the rules. Fundamentally changing the game in every way possible. Admittedly, that’s not an easy thing to do. Change comes with risk. It comes with hard work and uncertainty. It comes with an uncomfortable feeling that’s so strong, we often accept far less than we’re capable of, or deserve, to avoid it. The reason change is so empowering for challenger brands is that, as hard as it is to embrace when a brand is small, it’s exponentially harder for a big, established, successful brand.

Category leaders don’t like to tinker with their recipe for success. That can be smart for a while. But eventually, Fulton’s steamboat sails past all the people standing on the riverbank saying it could never be done. Change is difficult and it can be painful. But it’s a good kind of pain. And when you couple that change with courage, connection, creativity, and culture, there are very few things you can’t accomplish.

Challenger branding is not for the weak of heart. But for those of us who can’t imagine being in any other arena, there’s nothing better

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


We challenge underdog brands to think differently. We help them find their voice, and urge them to blaze new trails to make sure they stand out from the pack. Whether you need an agency of record or support on a project, we are here to help you win.