YoPro Know Logo White Reverse

Find Your Outlet

Caroline Jennings

Age: 24

Job: Director of Product, Cadre Health; Owner & Designer, Word Of Web

Location: Greenville, South Carolina

Caroline and I were connected through a mutual friend of ours and hit it off right away, mostly for our love of side hustles and networking. Caroline is actually the reason The YoPro Know got its good looks and I am so lucky to have had her help on this project because she truly is fantastic. If you’re interested in becoming a client, check Word Of Web out now. In the meantime, you won’t want to miss Caroline’s interview where we discussed everything from handling pride amidst a big career decision, balancing work and her side hustle, and beating burnout through an outlet like Word Of Web.

Give us a brief background on yourself.

I am born and raised in Greenville, South Carolina, and never thought I would actually end up here but, alas, I did. I did my undergrad at UNC Chapel Hill, where I studied psychology and neuroscience. I was one of those people that was a bit all over the place in college and really only decided what I wanted to do in my senior year of school, which was user experience design. I pretty much just taught myself that whole skill set and somehow managed to finagle an internship out in Boulder, so that's where I launched my very random start to my career. I ended up coming back to Greenville sort of thinking that it would be a jumping point to New York or San Francisco, but I ended up finding this job here that I loved. After a six-month unemployment period, I started my current job with Cadre Health about two years ago and have moved into several different roles since then. Starting in user experience design, I then moved to product management and am now the Director of Product.

What do you do in your current role?

When I joined the team, it was functionally just one product. We do health care technology and at the beginning, we just had various health care technologies that we developed in-house and I was just functioning essentially as a designer and researcher on those projects. Since then, we've really morphed into something much bigger and more exciting. We still develop our own technology and I still help oversee that, but the higher Cadre Health umbrella includes a playbook of different healthcare offerings that we take to hospitals and various health care providers. The ultimate goal of this playbook is to help improve operational efficiency and improve care outcomes in those hospitals. I like to say we are the Berkshire Hathaway of startups.

Tell us about a challenge you have experienced in your career and how you grew from that experience.

Honestly, my main challenge has just been myself. I think you know the whole mantra of you are your own worst enemy. It has been totally true for me. When I first moved back to Greenville, I did not think that I wanted to be here and my biggest challenge was seeing a job for what it was and removing any feelings about its location from the equation. I was gung-ho on going out to San Francisco and working for Google, so that was what I had my eyes set on. I was applying to the Twitters, Facebooks, and Googles of the world and even ended up getting a job offer with Google. Then, ironically, I got a job offer at Cadre that same week after six months of unemployment. All of a sudden, I was confronted with the choice of Google in San Francisco or Cadre Health startup in Greenville. Although I had always wanted to work for Google, there was this little voice inside my head that kept saying you need to stay here. Cadre was the better option with a better mission for me, whereas at Google, I would have been working in a research division and basically helping design better log in screens. I would be another cog in the giant machine and that made me realize that not only for my own career growth, but also just for the mission of healthcare, I needed to stay. I guess to answer your question, my main challenge was just stripping away pride from the equation. I realized that once I did that, Cadre really was the better move.

Going with your gut sometimes is the best thing that you can do. So talk about your team. It’s much smaller than Google!

When I started, I think there were about four of us. Now with all things said and done, we have about 30 employees that spread across the world. It has been pretty interesting being in this director role and managing people that I don't actually get to meet with on a day to day basis, and I think that has taught me a lot about the importance of clear communication. Our team dynamic is what has made Cadre a really good option for me. I've never worked with such a passionate and excited team that's also able to really get stuff done and isn't afraid to kill certain ideas when they're bad ones. With startups, you get so attached to your product and your mission that you forget what your audiences actually want. At Cadre, we're really good at spending time in hospitals talking to users. Our president was a CNO and COO and she knows a lot of health care people in the state and beyond, so I'd say the biggest aspect of our team dynamic that I appreciate is just the focus on who we are actually building these products for.

What is it like being a young woman in this field?

For starters, I try to act like I'm a solid 35. It's funny because I never mention my age, but I find that it comes up naturally sometimes. I don't think I look particularly young, but I don't look like I'm 35 either, and so sometimes I'll be in client meetings or I am making a pitch and someone in the room will say something along the lines of “you know, I think I'm about double your age.” My approach to this has morphed over the years. At first, I was just trying to avoid the question, but now I've actually started sort of diving into it and sometimes I'll be the first to initiate the age conversation if I can tell that it's a group of people that are going to be bothered by that. Turns out that health care is dominated by a lot of older men, so that tends to be something that comes up. To counter that, sometimes I'll just make a self-deprecating millennial joke.

Really? That works?

My favorite one to use right now is “So I'm working on technology for you and I want to get your input, so please stop me if I use any millennial jargon”, and then it never comes up. I never just openly announce that I'm 24, so I've tried to incorporate it into my work and I also tend to dress up more than some of my peers. I think the way that you dress and the way you present yourself has a big impact on how people treat you and especially that working relationship with clients and with your own colleagues and peers. As I said, I am a 24-year old that tries to act and dress like a 35-year-old. I oftentimes will have this moment when I look around and notice that I'm completely out of place. But if you don't let yourself feel out of place, then you won't be out of place.

So talk to me about what you do outside of the office and your side hustle.

I have always been one of those people that just has a million side hobbies and I drove myself crazy about a year ago because I was trying to block out time in my day for art and piano and my side hustle. I just realized I wasn't doing any of it particularly well, and so this was the phase of my life that I have now dubbed the entrepreneurial chapter. Most of my free time right now is going to Word Of Web, and it really started about two years ago. My dad is a dentist in Greenville and he's 65, so not a millennial (i.e., good at technology). His business had been suffering and he came to me and asked if I could help him because he had no idea why. I looked into it and immediately found it was because he did not have a website or any social media pages, so people just weren't finding him virtually. He kept telling me that back in the day, it was all word of mouth, and to his point, I found myself telling him that word of mouth is obsolete now. The new word is the word of web, so I had that little nugget in my head. I started actually seeing a lot of people like my dad with that need, especially in the Greenville area. Specifically, I started noticing it with different groups, including small business owners, non-profits, artists and influencers and/or bloggers. I started to realize there was actually a need for this and I think that's where the best ideas come from; not when you set out to be an entrepreneur, but when you stumble across an idea that you realize could actually help people and that you are well-positioned to help with. I officially started the company in May of 2019 and will officially begin taking clients next week.

Who are your clients?

So, really, the recurring theme that I've found with Word Of Web clients is that they have small budgets, they don't know any sort of tech, and they're scared or nervous and feel overwhelmed by the hurdle of getting a website. Because of this, I've had a really fun time sort of crafting my message and my brand and the way I work with clients. The main thing that I've been emphasizing to people is that I will help them, but at the end of my whole process, I actually will train people on how to make basic edits themselves. A lot of companies will charge $200 per hour just to make edits, but I just believe that once you have a website, it should be yours, but I am always free to help if you need me. I feel that you should be in control of your digital future.

How has your work life been impacted, if at all, by your side hustle and how did you approach your boss about it?

I guess I'm still figuring that out largely. I think in tech, more so than any other industry, it's kind of an understanding that people have side hustles. In fact, I don't really know anyone in tech that doesn't have a side hustle of some sort. I've just had to be really intentional about allocating the proper resources and time to each commitment. I've tried to be better about time chunking various responsibilities. I usually make Word of Web an early morning and nighttime thing, and then try to leave time to sleep.

What is your "Why" behind your side company?

It's kind of funny you ask that because I've noticed that I've asked myself many times now, why am I doing this? To those questions, I'd say for two reasons: one, it feels like too good of an idea and there feels like too much of a need to pass it up. I used to work at this startup accelerator in San Francisco where I interviewed entrepreneurs and asked them what entrepreneurship means. The resounding response that I heard was that when you feel so compelled to do something, there's no way you can just not do it. The second reason I'm doing it is truly that it's an outlet for me and I think you’ll understand this too. I think there's a misconception that burnout can be prevented by just resting. Well, I'm the type of person who does not get over a stressful week by resting. It’s by working on the things I love. Working in an office and working in a larger company now, there are a lot of things that are just out of your control and some days I come home and I'm frustrated because someone hasn't gotten back to me, or this project is delayed. When that happens, my outlet is Word Of Web because it’s something that I can organize and put creativity into; it is also a good respite from the grind of work.

What do you want experienced professionals to know about what we want and need as young professionals to help us grow into leadership?

I would say honesty. I mean, that's a super simple answer, but I would like for someone to tell me “it's going to be tough sometimes and there are times that will absolutely suck.” So that's one form of honesty. The other type is more along the lines of constructive feedback. I personally get so annoyed when you know I'm running a pitch by someone and they say, “Oh that's great.” No, I actually want you to give me your opinion and sometimes it can be as small as “you slouch a lot,” or “you say 'like' a lot.” I think having mentors that aren't afraid to call you out is super important because I think there aren't enough people in the world that put a mirror up to you. It's often perceived that those mirrors have to be your best friends, but if you want to progress in your career, those mirrors should really be the people that you want to aspire to be like.

The YoPro Know's Takeaways:

– Sometimes you need to strip pride away to make a career decision

– Initiate the age conversation right away if you're working with a group of people that are going to be bothered by that

– Dress well; it has a big impact on how people treat you

– If you don't let yourself feel out of place, then you won't be out of place.

– The best ideas do not come from when you set out to be an entrepreneur, but when you stumble across an idea that you realize could actually help people

– Choosing a job because of its mission, not its name

Check it out: Cadre Health, Greenville, South Carolina, Word Of Web

Share this Article

Transforming Talent Retention

Get The Free Report

Learn What Motivates Future Leaders to Join, Stay, and Grow Your Company

By identifying that all generations have diverse mental health needs and benefit desires — comprehensive wellness programs, robust mental health support, and meaningful benefits — we allow businesses to foster a more committed and productive workforce.