Meet Jake Beckstead | Chief Marketing Officer at Bailey’s Group

We had the good fortune of connecting with Jake Beckstead and we’ve shared our conversation below.

Hi Jake, we’d love to hear about how you approach risk and risk-taking.
Risk, to me, is about stepping into uncertainty with purpose. I don’t chase risk for its own sake, but I do believe progress doesn’t happen without it. Any time you launch a new campaign, pivot a strategy, or advocate for a bold idea, you’re putting yourself out there.

In my career, the moments I’ve grown the most were the moments I had to push past comfort. I’ve taken creative risks — trying new approaches when the “safe” option was easier. I’ve taken professional risks — raising my hand for projects or responsibilities that stretched me. Sometimes those risks pay off beautifully, and sometimes they teach hard lessons. But either way, risk has always been the door to growth. Playing it safe might feel easier, but it rarely leads to meaningful change.

Let’s talk shop? Tell us more about your career, what can you share with our community?
My career has been less about following a straight path and more about building on opportunities that allowed me to blend creativity with strategy. I didn’t wake up one day as a CMO, it’s been a process of learning, stretching, and sometimes stumbling. What sets me apart is that I’ve never seen marketing as just “advertising” or “selling.” To me, it’s about storytelling. It’s about helping people make sense of something complicated, stressful, or overwhelming, and giving them clarity and confidence.

At Bailey’s Moving & Storage, that story matters because we’re not just moving boxes; we’re moving people’s lives, their memories, their businesses, and their futures. I’m proud of how we’ve built a brand voice that positions the customer as the hero — not us — and shows how we can walk alongside them as a guide. That shift in perspective has helped us connect with people in a way that feels authentic and lasting.

Getting here wasn’t easy. Like many professionals, I had to overcome doubts, rejections, and moments where things didn’t go the way I planned. There were times I had to fight for ideas that I believed in, and times I had to admit I was wrong and learn quickly from it. The common thread was persistence and the willingness to keep showing up, even when it was uncomfortable.

One of the most important lessons I’ve learned is that clarity beats cleverness. If you can clearly articulate who you are, what you do, and why it matters, people will respond. Another lesson is that leadership isn’t about having all the answers, it’s about creating an environment where others can thrive and bring their best ideas forward.

What I want the world to know about me and about Bailey’s is that we genuinely care. We care about the families who trust us with their homes, the businesses who trust us with their growth, and the employees who trust us with their livelihoods. Our story is one of service, resilience, and community. And if there’s one thing I hope people see, it’s that moving forward — whether in business or life — doesn’t have to be done alone.

Any places to eat or things to do that you can share with our readers? If they have a friend visiting town, what are some spots they could take them to?
If a close friend were visiting, I’d want them to experience both sides of what makes Colorado special — the charm of our local towns and the beauty of the mountains.

I’d start by showing them around Parker and Castle Rock. Both towns have grown so much but still hold onto a fun, community-driven vibe. You can spend time wandering the shops, eating at a local café, or enjoying a good meal at one of the local restaurants; I’m a big fan of Venalonzos in Parker. There’s always something happening — farmer’s markets, concerts, festivals — and it feels like a place where people genuinely connect.

But Colorado isn’t Colorado without heading into the mountains. Woodland Park is one of my favorite spots — you’re tucked right against Pikes Peak, surrounded by forest, but still close enough to civilization to enjoy a nice dinner afterward. If we wanted more of the outdoors, I’d take them camping near Deckers or exploring the trails along the Platte River. There’s something about sitting around a fire in the evening, under the Colorado stars, that gives you the full sense of this place.

And if they were up for more adventure, we’d make our way into the Arkansas River Valley. It’s rugged, beautiful, and offers everything from rafting to hiking to just taking in the views. To me, that valley feels like the best of Colorado — open skies, rushing water, mountain towns, and a pace that reminds you to breathe.

What I love about showing people Colorado is that you don’t need big city attractions to have an amazing experience. It’s the mix of small-town life, natural beauty, and a little bit of adventure that makes this area unforgettable.

Shoutout is all about shouting out others who you feel deserve additional recognition and exposure. Who would you like to shoutout?
Absolutely — I don’t believe anyone gets where they are alone. My story is really a mix of people who have poured into me over the years. Professionally, I’ve been fortunate to work with leaders and mentors who trusted me with big responsibilities before I was fully ready. That trust pushed me to grow quickly and taught me how important it is to give others the same kind of opportunity.

On a personal level, my wife has been a steady source of encouragement and perspective. She keeps me grounded when the demands of work could easily take over and reminds me of what matters most. And of course, my kids inspire me more than they realize — they’re a daily reminder of why I want to build something meaningful, not just for customers and colleagues, but for the next generation watching me live it out.

I’d also give credit to the many authors and thinkers who’ve shaped how I approach leadership and creativity — people like Donald Miller with Building a StoryBrand and Marcus Sheridan with They Ask, You Answer. Their ideas about clarity, service, and storytelling have had a lasting impact on how I think and how I lead.

If there’s one thread through all of this, it’s gratitude. I’m here because of the people who believed in me, challenged me, and walked alongside me — and I hope I can play that same role in the lives of others.

Website: https://jake.beckstead.net

Linkedin: https://www.linkedin.com/in/jacob-beckstead/

Other: https://baileysallied.com (Bailey’s Moving & Storage)

Image Credits
Credit Bailey’s Moving & Storage