Check Out Jen Shaefer’s Story

Today we’d like to introduce you to Jen Shaefer.

Hi Jen, can you start by introducing yourself? We’d love to learn more about how you got to where you are today?
My journey as an entrepreneur began earlier than most—I was just eight years old when I asked for a cash register for Christmas. I always knew I wanted to run my own business; I just hadn’t figured out what that business would be. Fast forward to my Sweet 16, a milestone that unexpectedly shaped my future. I meticulously planned every detail—the playlist, the floor plan, the menu, the dress code, and the décor. The party was a blast, but the real turning point came afterward when my older brothers told me, “You’re really good at this—you should do it for a living.” Until that moment, I had never considered event planning as a career, but from that day forward, I knew exactly what I wanted to do.

Eager to explore the industry, I started working for a catering company almost immediately. I fell in love with the process—setting up décor, witnessing different traditions, and seeing how events brought people together. That passion led me to study communication and entrepreneurship in college, with a clear goal in mind: one day, I would open my own wedding venue.

After graduating, I immersed myself in the industry, working for multiple venues and planning companies, absorbing every lesson and loving (almost) every moment of it. In 2018, I took the leap and launched my own planning company, Southern Skies Events. I poured everything into building my brand in the Triangle, working seven days a week to establish my name. Now, after nearly seven years in the industry, I’m beyond excited to be stepping into my next chapter—opening my own wedding venue, The Skyroom NC, in partnership with my dad. It’s the dream I’ve been working toward for years, and I can’t wait to bring it to life.

Would you say it’s been a smooth road, and if not what are some of the biggest challenges you’ve faced along the way?
The journey was certainly not without its challenges, but I believe that any dream worth pursuing comes with its fair share of obstacles. When I launched Southern Skies, I was only two years in when COVID hit. Thankfully, event planning wasn’t my full-time focus at the time, but that year was a defining moment for everyone in the industry. In North Carolina, I believe we emerged from it stronger and more connected as a community of event professionals.

The bigger challenge, however, was finding the perfect land for my venue dream. Having spent years in events at this point, I had seen incredible venues all across the country—some I adored, others that didn’t quite resonate with me. I knew from the start that I wanted to build from the ground up, and I was unwavering in my vision—it had to be just right. The search was daunting; I needed at least three acres, close enough to major cities like Raleigh-Durham, yet secluded enough to offer couples the intimacy they deserved. Time and again, we found beautiful properties, but each came with deal-breaking limitations.

Then, we found it—a stunning 10-acre piece of land in Moncure that checked every box. Not only did it meet all my requirements, but it also had a rare, tranquil energy that immediately felt like home. It’s a space that brings me peace, and my greatest hope is that every couple, client and vendor who steps onto the property feels that same sense of serenity and magic.

Thanks for sharing that. So, maybe next you can tell us a bit more about your work?
I am, at my core, a business woman. I thrive on writing business plans, mapping out strategies, forging meaningful partnerships, and tackling challenges—but above all, my greatest passion is serving others and helping them create some of the most unforgettable moments of their lives.

Currently, I own three businesses, all centered around weddings and events. My first, Southern Skies Events, has been bringing incredible celebrations to life for nearly seven years. Then there’s Wedding Crasher, a mobile app designed to enhance the guest experience, which was born out of the challenges of COVID when events as we knew them were put on hold. And finally, my most ambitious venture to date, The Skyroom NC—a wedding and event venue set on 10 scenic acres in Moncure, NC. I poured my heart and soul into creating a versatile space that not only serves as a beautiful backdrop for events but also provides clients with the tools, resources, and support to make their experience truly seamless. Now, in 2025, there’s a sweet synergy between all three businesses that allows them to coexist, which is really special for me.

What truly sets my businesses apart is the people behind them. Having been an athlete all my life, I aim to bring the core principles of teamwork into every event. As planners, my team and I act as the “coaches” on event day—overseeing the big picture, equipping our clients with the right tools, and ensuring every element comes together flawlessly. But we’re just one piece of the puzzle. Our incredible network of vendors, each bringing their own unique passion and expertise, is what truly makes each event exceptional.

Even after 18 years in the industry, I still get butterflies before every event—the same way I did before a big game. I always told myself that when that feeling of nervous excitement fades, it will be time to step back. Thankfully, that day hasn’t come yet, and I hope it never does.

Can you talk to us a bit about the role of luck?
I believe luck plays a role in every positive milestone in our lives—but I also believe that luck is amplified by passion and hard work. Do I work hard? Absolutely. Do I consider myself lucky? Without a doubt. Every day, I have the privilege of living my entrepreneurial dream, doing what I love, and building something meaningful. To me, that’s the ultimate kind of luck—one that’s earned through dedication and a relentless pursuit of what feeds my soul.

Contact Info:

• Website: https://theskyroomnc.com/ or https://southernskiesevents.com/
• Instagram: https://www.instagram.com/theskyroomnc/ or https://www.instagram.com/southernskiesevents/

Image Credits
Libby Mcgowan Photography
Ezer Photo
Joe Payne Photography
The Axtells Photo Films
Krista Stevens Photography
Erin Michele Photos