

Today we’d like to introduce you to Caroline Jennings.
Hi Caroline, we’re thrilled to have a chance to learn your story today. So, before we get into specifics, maybe you can briefly walk us through how you got to where you are today?
I launched Word of Web back in 2019 as my ‘side hustle’ while I was working for a health tech company in Greenville. At first, I was just having fun building websites for friends and family. I wasn’t charging anything for them because I just saw it as a hobby. After a while, I realized there was demand beyond friends and family, so I started taking on paying clients – mainly entrepreneurs and small business owners in the Upstate area. Eventually, I had more website work than I could handle, so I decided to quit my job and take Word of Web full-time. That was in January 2020, so I was in for a fun surprise a few months later when the world shut down.
Fast forward to now – Word of Web is still going strong, with a team of 8 amazing creatives working remotely from across the country (from San Diego to San Francisco, to Greenville, to Chicago). We’ve had the privilege of working on some incredible projects over the years: working with the military to design a mental health platform for veterans, building South Carolina’s 988 Crisis Line website, creating a digital art portfolio for the AC Hotel, and writing 300+ physician bios for a hospital system in Hawaii (to name a few).
Of course, there have been significant ups and downs over the years, but I couldn’t be happier with what our team and clients have built together. At this point, it feels like the business has taken on a life of its own, which is crazy, considering it started off with me making Wix websites in my spare time!
We all face challenges, but looking back, would you describe it as a relatively smooth road?
The road has definitely been bumpy from time to time. For the first couple of years, my biggest challenge was figuring out how in the world to run a business. I was a UX designer who had studied psychology/neuroscience in school, so entrepreneurship was far outside of my comfort zone. I had never even taken a single economics or business class in college. But after a while, I learned there wasn’t any sort of entrepreneurship rule book and that everyone was figuring it out as they went, so I started to feel more comfortable trusting my instincts – and leaning on Google, mentors, and colleagues when I needed help.
It wasn’t until after I got comfortable with the day-to-day of running a business that I started experiencing heavier, more abstract challenges – like imposter syndrome and burnout. These challenges have been a fairly consistent background noise throughout these past 3 years running Word of Web, but I have learned to manage them and embrace them as a part of the journey.
Thanks for sharing that. So, maybe next you can tell us a bit more about your business?
Word of Web is a web design studio specializing in strategy, user experience, and analytics. We create websites for businesses all over the world to help them generate more leads and close more sales.
We’re not a traditional web design company that simply asks what you want and builds it. We think of ourselves as creative architects whose job is to translate your vision into a blueprint that we can implement together and continuously refine. It’s a smarter, consultative approach where every decision is based on your unique business and customer goals – not just on what looks best.
Can you share something surprising about yourself?
For the past few months, I’ve been living somewhere new each month and working out of coworking spaces. That’s the great thing about running an online business – our team can work from wherever! My coolest destination so far has been Buenos Aires, Argentina.
Contact Info:
- Website: www.wordofwebdesign.com
- Instagram: https://www.instagram.com/wordofwebdesign/
- Facebook: https://www.facebook.com/wordofwebdesign
- Youtube: https://www.youtube.com/channel/UCwzCWAaQhEacd7oa6dL6f1w