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Conversations with Kym Jenkins

Today we’d like to introduce you to Kym Jenkins.

Hi Kym, can you start by introducing yourself? We’d love to learn more about how you got to where you are today?
People often assume my story started with marketing. Truth is, it started with curiosity.

I’ve always been fascinated by why people care about certain things. Why do some brands become movements while others become background noise? Why do some experiences stay with you for years while others are forgotten before you make it to the parking lot? I was the kid pulling things apart just to figure out how they worked, except my “things” were people, ideas, experiences, and culture.

That curiosity turned into a career I never could have mapped out.

For the last 16 years, I’ve been fortunate enough to work across marketing, creative direction, brand strategy, content, live experiences, and storytelling. I’ve worked with Fortune 500 companies, nonprofits, churches, entrepreneurs, entertainers, and organizations connected to brands like Lyft, Dark & Lovely, McDonald’s Gospel Tour, Sally Beauty, NBC5, Shondaland, and professional sports organizations. Every opportunity taught me something new about people. At the end of the day, marketing has never really been about marketing. It’s about human behavior.

Some people build campaigns. I build moments people talk about months later.

I’m obsessed with creating experiences that make people feel something. Whether I’m producing an event, directing a commercial shoot, developing a social strategy, or reimagining an entire brand, I’m always asking the same question. “What story are people going to tell after this is over?”

That’s the heartbeat behind FIFTY55, my creative house where strategy, creative direction, and experiences all live under one roof. I like to say we’re in the memory-making business. We help brands become unforgettable. We don’t just help people look good online. We help them create experiences that people want to belong to.

The funny part is, my own life has been one giant rebrand.

A few years ago I made the decision to completely change my health. Since then I’ve lost over 200 pounds, but the weight was honestly the smallest transformation. I gained discipline. I gained confidence. I gained perspective. I learned that real transformation almost never happens overnight. It’s built through thousands of ordinary decisions that nobody applauds. That lesson follows me into every room I walk into. Whether I’m helping someone build a company or rebuild their confidence, the process is surprisingly similar.

One thing about me is I don’t believe creativity belongs in a box.

I love sitting at the intersection of creativity, technology, business, faith, psychology, and culture because that’s where the magic happens. Some days I’m consulting as a Fractional CMO. Other days I’m producing immersive experiences, mentoring creative entrepreneurs, hosting conversations, or dreaming up ideas that don’t have a category yet. Honestly, that’s my favorite place to be. If it doesn’t exist, let’s build it.

The older I get, the less interested I am in chasing trends. I’m much more interested in creating work that outlives algorithms.

My dream isn’t to become the most famous creative director. It’s to build ideas, brands, communities, and experiences that shift culture and give people permission to think bigger than they did before they met me.

If someone walks away from an experience I created feeling more inspired, more courageous, or more hopeful than when they arrived, I did my job.

That’s the kind of success I’m after.

Alright, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
Absolutely not. If anything, my career has been beautifully unconventional.

I’ve never taken the “safe” route. I’ve bet on ideas before they made sense on paper. I’ve walked away from opportunities that looked good because they didn’t align with the kind of impact I wanted to make. I’ve reinvented myself more than once, and every reinvention required me to become someone new before the world recognized it.

One of the biggest challenges has been helping people understand that creativity is a business strategy, not just a design service. For years, people saw creative work as the “pretty part” that happens at the end. I’ve spent much of my career helping organizations realize that creativity belongs in the boardroom. The right strategy, story, and experience can completely change the trajectory of a brand.

Another challenge has been learning to value my own expertise. Like many creatives, I started by saying yes to everything. I wanted to prove myself. Over time I realized that saying yes to everything often meant saying no to the work I was actually called to do. Learning to charge appropriately, set boundaries, and confidently own the value I bring has been one of the most important lessons in my career.

Personally, one of my greatest victories came through my health journey. Losing over 250 pounds taught me that transformation isn’t about motivation. It’s about consistency. That experience changed how I approach everything. Business. Leadership. Relationships. Creativity. I don’t expect overnight success because I’ve lived through what it takes to build something one intentional decision at a time.

There have been seasons of uncertainty, projects that didn’t go the way I planned, ideas that didn’t land, and moments where I questioned what was next. But looking back, every setback gave me something I couldn’t have learned any other way. It sharpened my instincts, strengthened my faith, and reminded me that resilience is one of the greatest competitive advantages a person can have.

Now, I don’t see challenges as interruptions to the journey. They are the journey. Every obstacle has expanded my perspective, stretched my creativity, and prepared me for opportunities that were bigger than anything I could have imagined.

Thanks – so what else should our readers know about your work and what you’re currently focused on?
At my core, I’m a Creative Director, Marketing Strategist, and experience architect. I help brands, organizations, and leaders become impossible to ignore.

Most people think marketing starts with social media or a logo. I think it starts with human behavior. Before I ever ask, “What should we post?” I’m asking, “How do we want people to feel? What do we want them to believe? What story will they tell after they experience us?” That’s where the magic happens.

Through FIFTY55, I partner with brands, nonprofits, churches, entrepreneurs, and organizations to build marketing strategies, creative campaigns, brand positioning, live experiences, and content ecosystems that actually move people. Whether I’m serving as a Fractional CMO, producing a large-scale event, directing a creative campaign, or helping an entrepreneur find their voice, my goal is always the same. Create something memorable enough that people can’t help but talk about it.

If I had to describe my specialty, I’d say I connect dots other people don’t see.

I’m naturally wired to think across disciplines. I pull inspiration from psychology, hospitality, technology, architecture, entertainment, faith, design, and culture, then translate all of that into experiences that feel fresh, intentional, and deeply human. I don’t just ask what looks good. I ask what works, what lasts, and what people will remember.

Ironically, I’m probably best known for helping people see possibilities they couldn’t see for themselves.

Clients often come to me asking for better marketing, but they leave with something much bigger. They leave with clarity. Sometimes the strategy changes. Sometimes the brand changes. Sometimes the business changes. Occasionally, their confidence changes too. I love helping people uncover the thing that has been there all along and giving it language, structure, and momentum.

What I’m most proud of isn’t one campaign or one client.

I’m proud that I’ve built a career by staying curious. I’ve never wanted to become known for one industry because I believe great ideas don’t belong to one industry. Some of my best ideas for churches come from hospitality. Some of my best ideas for businesses come from Broadway. Some come from museums, airports, theme parks, restaurants, or conversations with complete strangers. Curiosity has been one of the greatest assets in my career, and I hope I never lose it.

I think what truly sets me apart is that I don’t see marketing as promotion. I see it as discipleship, hospitality, and experience design. Every interaction with a brand is teaching people what to believe about it. Every touchpoint is either building trust or breaking it. That’s why I obsess over the details that most people overlook.

People often tell me that after one conversation with me, they don’t just leave with ideas. They leave believing bigger is possible. Honestly, that’s the legacy I want more than anything. I want my work to inspire people to create with more courage, lead with more intention, and build things that outlive them.

If people remember me years from now, I hope it’s because I didn’t just help brands grow. I helped people think differently about what’s possible.

Where do you see things going in the next 5-10 years?
I think we’re entering one of the most exciting seasons our industry has ever seen.

For years, marketing has been about getting people’s attention. Over the next five to ten years, it will be about earning people’s trust. AI is making it easier than ever to create content, write copy, generate images, and automate production. That’s incredible, but it also means the internet is becoming noisier by the minute. When everyone can create content, content alone is no longer the competitive advantage.

Humanity is.

We’re going to see a major shift from content creation to experience creation. People don’t just want something to watch. They want something to participate in. They want community. They want belonging. They want stories they can step inside of. The brands that win won’t necessarily have the biggest marketing budgets. They’ll be the ones that make people feel seen, valued, and connected.

I also believe the role of the Creative Director is evolving. We won’t just be responsible for visuals or campaigns. We’ll become architects of entire ecosystems. That includes customer experience, internal culture, digital products, live events, partnerships, AI integration, and community building. Creativity is becoming less about aesthetics and more about designing how people experience a brand from beginning to end.

Another shift I’m excited about is the democratization of great ideas. You no longer need a massive agency or Fortune 500 budget to build something remarkable. A solo creator with a clear point of view, the right technology, and a deep understanding of people can build a global brand from their laptop. That’s changing who gets a seat at the table, and I think that’s a beautiful thing.

Personally, I think we’re moving into what I call the Experience Economy 2.0. The future belongs to brands that don’t just sell products or services. They create moments, memories, and movements. The companies that thrive will think more like hospitality brands, entertainment companies, and community builders than traditional advertisers.

Through all of the technological changes, one thing will remain true. People will always crave connection. Technology will continue to evolve, platforms will come and go, and algorithms will change, but human nature won’t. The creatives and brands that understand people better than anyone else will always have an advantage.

That’s why I’m incredibly optimistic about the future. AI won’t replace great creatives. It will raise the standard. The future belongs to the people who know how to blend strategy, empathy, imagination, and technology to create experiences that people genuinely can’t stop talking about.

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