Story & Lesson Highlights with Jill Cherry of Tampa, Fl

Jill Cherry shared their story and experiences with us recently and you can find our conversation below.

Jill, so good to connect and we’re excited to share your story and insights with our audience. There’s a ton to learn from your story, but let’s start with a warm up before we get into the heart of the interview. What do the first 90 minutes of your day look like?
The first 90 minutes of my day consist of waking up, coffee, riding my bike to the gym working out and coming back home to get my day started.

Can you briefly introduce yourself and share what makes you or your brand unique?
Hi, I’m Jill Cherry, founder of Cherry Picked Web Co.—a boutique website design studio that specializes in creating high-converting, personality-packed websites exclusively for chiropractors. We’ve had the privilege of serving over 400 practices and counting, helping doctors elevate their online presence, attract their dream patients, and grow thriving businesses rooted in service and purpose.

What makes us unique? We don’t just build pretty websites. We create strategic digital homes that work for our clients—day and night—generating leads, building trust, and making it easy for people to say “yes” to care. Our designs are clean, professional, and conversion-driven, but what really sets us apart is how deeply we understand the chiropractic world. Because I’m married to a chiropractor, and I live this lifestyle—we know the rhythms of a practice, the heart behind the mission, and the specific messaging that resonates.

Right now, we’re focused on expanding our offerings with tools and automation that support chiropractors beyond the website—like our new service called Convey, which helps practices stay top-of-mind through automated texting and email follow-up.

At the end of the day, my mission is simple: help chiropractors do more of what they love—taking care of people—while we take care of their online presence.

Thanks for sharing that. Would love to go back in time and hear about how your past might have impacted who you are today. What did you believe about yourself as a child that you no longer believe?
That I’m not worthy.

What did suffering teach you that success never could?
Suffering taught me to listen to 2 Corinthians 12:9 “But he said to me, ‘My grace is sufficient for you, for my power is made perfect in weakness.’

When everything is going right, it’s easy to ride the wave, stay busy, and not question much. But in the hard seasons—the moments when nothing seems to be working, when doubt creeps in, when it feels like the doors just keep closing—that’s when I had to get brutally honest with myself. Who am I really? What do I believe in when everything is stripped away? What am I being called to create, not just to succeed, but to serve?

Suffering slowed me down and made me feel things I would’ve otherwise ignored—fear, grief, resentment, burnout. But it also woke up a deeper part of me that knew I was meant for more. It clarified my mission. It gave me grit. It made me tender. And most importantly, it made me unshakeable in my faith.

Success looks shiny, but suffering built the foundation (my faith in Jesus is the foundation). It’s where I found my voice. It’s what pushed me to create something bigger than myself. And it’s why I now have a business that not only supports my family, but helps hundreds of chiropractors grow theirs.

Alright, so if you are open to it, let’s explore some philosophical questions that touch on your values and worldview. How do you differentiate between fads and real foundational shifts?
For me, the difference between a fad and a foundational shift is fads are fast, foundational shifts are slow, but sure.

Fads are loud. They usually come with hype, buzzwords, and a feeling of urgency—like if you don’t jump on it now, you’ll miss out. But foundational shifts? They’re quieter. They often start with a subtle tension, a sense that something isn’t working anymore, or that there’s a better way forward. They build over time. They change how we think, not just what we do.

In my work designing websites for chiropractors, I’ve seen trends come and go—fonts, color palettes, platforms, even the latest marketing “hacks.” I don’t get caught up in those. I watch behavior. I listen to what people really need. Foundational shifts happen when technology, psychology, and consumer expectation all move in the same direction. It’s not just a new look—it’s a new lens.

The key is this: fads demand attention. Foundational shifts earn it by creating real value.

So when I evaluate something new, I ask myself:

Does this solve a root problem?
Will it still matter in 3 years?
Does it align with my mission and how I want to serve?

If the answer is yes, it’s worth investing in. If not, it’s probably just noise.

Okay, so before we go, let’s tackle one more area. What is the story you hope people tell about you when you’re gone?
That I was saved by grace. That I was kind and honest. That they felt genuinely loved by me. That I loved my family more than anything else and that I had a great smile that could light up any room.

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