A marketing leader and a culture builder bring different strengths to the same challenge: making a challenger brand impossible to mistake for anyone else.
Underdog competes in a category built around bigger bonuses and bigger promises. Its first national brand campaign took a different route: make sports more fun, then build a brand people can recognize long after a promotion ends.
I sat down with Devin Bellamy, Underdog’s Senior Director of Integrated Marketing, and Mike Posner, Head of Executive Development, to talk about two sides of that work. Devin looks at the marketing choices that make the brand stand apart. Mike looks at the culture and leadership that help people bring those choices to life. Together, they show why moving at the speed of culture starts before the moment breaks.
In a category where getting rich can easily become the whole story, Underdog wanted to make sports more fun. Mike described the difference this way: “We really think of ourselves as a vehicle where people can really enjoy the experience that they’re having rather than play with some sort of outcome in mind.”
The brand needed to express that point of view. The Dog, Underdog’s new brand character, is part guru, part companion, and part social liability. He’s unpredictable and unhinged, but still charming enough to make you want to see what he’ll do next.
When the team brought the brief to comedy veterans Jody Hill and Paul Walter Hauser, they understood the assignment. Hill protected the weirdness on set, leaving room for uncomfortable pauses and unexpected moments. Hauser had room to improvise within the character the team had built, and gave The Dog his rascal soul.
At times, the team wondered whether the work was getting too absurd. Instead of sanding down the parts that made it distinctive, they trusted the people they had brought in to make it great. Devin put the ambition simply: “We wanted to have a POV. We wanted to have fun.”
That’s the marketing lesson: define what makes the idea yours, then give the right creative partners room to bring it to life. If every unusual edge gets sanded down in approvals, the work can end up looking like the category it was meant to challenge.
Underdog has to respond while a cultural moment is still happening, not a week later after a 10-person approval chain. Devin’s answer to how the team moves quickly without losing the brand: “The secret is that speed is the result of clarity.”
That work starts long before a moment breaks. The team needs to know what the brand sounds like, what it finds funny, what it would never say, and where legal and compliance boundaries sit. Once those guardrails are clear, Underdog gives people close to the work authority to act.
Devin is clear that autonomy doesn’t mean recklessness: “It doesn’t mean that everyone’s just acting recklessly or that your standards disappear. It means that we trust smart people to use their judgment.” Dedicated budgets and lean approval chains help turn that trust into action.
The team also expects some ideas to miss. Devin said they try to treat misses as learning: what didn’t work, why, and what should change next time. That approach has led to activations like Unethical Hoops, an Operation-style board game poking fun at one of the NBA’s most-fouled players. It earned a cease-and-desist and kept people talking for weeks. More recently, the team brought that same mentality to a Lane Kiffin dartboard ahead of the Ole Miss game.
Culture is not something a company can leave to chance while it focuses on the next campaign. Mike put it plainly: “Culture happens regardless, whether you do it on purpose or you do it on accident. It’s the norms, the behaviors, the expectations that start to emerge.”
Underdog is fully remote, with hundreds of employees. Mike said the company did not start by writing a list of values and stopping there. “Instead of just writing a bunch of values, it’s actually trying to see what the unsaid values already are and to name those things as virtues and then to continue to perpetuate them.” At Underdog, that means connecting its cultural pillars to recruiting, recognition, and the way people work together.
The company also brings employees together through team off-sites and an annual Camp Underdog. The week combines work and play, from AI hackathons and cultural awards to sports competitions, ziplining, and a hot-wings challenge. Those shared experiences help people build relationships beyond their day-to-day work, making collaboration and honest feedback easier when they return to it.
For CMOs, the takeaway is that culture has to show up in the conditions around the work: who gets hired, what behavior gets recognized, and whether people have the trust and tools to act. A values slide cannot do that on its own.
Underdog’s employees are close to the product and the audience. They play the games alongside customers, experience the same highs and frustrations, and share feedback in one of the company’s busiest Slack channels. Devin said, “We are watching sports. We are playing all of our games and are right there alongside all of our customers.”
That proximity gives the team a built-in gut check. When it considers a product or campaign idea, it can ask: Will this make sense to the sports fan watching the game? Will it cut through? Does it make the experience more fun? For a concept like Unethical Hoops, the team already understood the joke because it is part of that world.
That closeness is a useful starting point, not a replacement for customer research. Build teams with real knowledge of the people you serve, then validate the assumptions that matter most with those people.
Before the next moment hits, get clear on four things:
· Point of view: What can our brand say about this moment that others can’t?
· Guardrails: What are the legal, compliance, and brand boundaries?
· Authority: Who can make the call, and what budget or approval is already in place?
· Learning: If the idea misses, how will we capture what happened and use it next time?
Devin and Mike approach the opportunity from different sides. The strongest work happens when marketing and culture are in the room early, so the team can move quickly and still make work that feels unmistakably its own.
Hear Devin Bellamy and Mike Posner on Question Everything for more on building Underdog’s brand and culture, including the company’s reaction to Sydney Sweeney’s controversial ad for Novig. Find the full conversations on YouTube, Apple Podcasts, or Spotify.
Part interview, part therapy, part Price Is Right, Question Everything puts CMOs and marketing leaders in the hot seat. While they face off against our game board, listeners hear the wins, mistakes, and hard-earned lessons of leaders who are all daring enough to be curious.
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