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Daily Inspiration: Meet Chesley Gaddis


Today we’d like to introduce you to Chesley Gaddis

Alright, so thank you so much for sharing your story and insight with our readers. To kick things off, can you tell us a bit about how you got started?
I took the job at Intrepid in 2005 to assuage my parents’ “suggestion” that I get a “real” job (at the time I was riding and training at a horse farm). I figured I’d be here a year or two until I found something I was passionate about. Fast forward 18 years, and I’m still here! It turns out that you don’t have to be passionate about the day-to-day – what’s more important are the people with whom you’re working and the vision you’re aiming to accomplish.

After spending two years in a service role, I was promoted to a consulting position. I found out quickly that this English Major wasn’t wired for spreadsheets and insurance jargon. I told our president and my mentor (Liz Frayer) that I would be looking for other opportunities, but I’d stay as long as she needed me to transition the role to someone else. She surprised me by giving me the opportunity to create a job within Intrepid that catered to my natural skill set and enjoyment. I developed our Communications Director position, in which I took the complicated concepts of insurance and translated them to the everyday consumer. It was fun!

After about a decade in that role, Liz pushed me to be in sales. Being pregnant with my first child, and my husband working on a startup that wasn’t yet generating revenue, I wasn’t comfortable moving into a commission-based model. Six months later, I caved and haven’t looked back.

Sure, sales can be stressful, but connecting with new people and learning their stories is incredibly meaningful to me, and has been beyond impactful both personally and professionally. I’ve met some amazing people from all different backgrounds; and while not all of them have turned into clients, many have turned into friends. It doesn’t get much better than that.

I’m sure it wasn’t obstacle-free, but would you say the journey has been fairly smooth so far?
The road has been about as smooth as Dekalb Ave. before the City finally got around to paving it in 2023. There are a lot of “potholes” out there, but that’s what makes the journey exciting and rewarding. I’ve been told “no” more times than I’d like to admit, but over the years I’ve learned that the people who say “yes” are worth all of those nos.

I’d never really been in sales before (except the one time I got roped into a pyramid scheme without realizing it), so I had no clue what I was doing. I don’t do scripts, but I also didn’t really know what to say. Being an Atlanta native, I figured I’d have a head start. Well, it turns out that Atlanta is a big city with a lot of transplants, and no one really cares where you’re from. I was basically trolling the Atlanta Business Chronicle to even figure out who to call.

Alright, so let’s switch gears a bit and talk business. What should we know about your work?
Our firm helps companies control the skyrocketing costs of healthcare for their employees. We implement creative strategies to navigate the system, and teach our clients’ employees the value of their health plans and how to be better consumers of their healthcare dollars. Historically, consumers haven’t had a lot of choice when it came to lowering their healthcare spend, but after the ACA went into effect, they’ve had to take a much more proactive and participatory approach. Most laypeople don’t know they have the tools – our job is to educate them on how to use those tools to “stick it to the man.”

Our Atlanta office is all women, and we love to be the “cool kids on the insurance block” (albeit the bar is low…), but we are super nerdy about being creative pioneers in the benefit consulting space. 20 years ago, it was mostly a spreadsheet gig – that’s just not the case anymore. We don’t tell folks we can negotiate their renewal down a point or two – that’s a lazy Band-Aid approach that sounds great at first, but it really doesn’t make an impact from a long-term planning perspective. We implement sustainable, scalable strategies that actually make a meaningful difference down the road.

What were you like growing up?
A lot of people might not believe this, but I was a pretty shy kid. I would never correct people when they called me Chelsey instead of Chesley, and when my mom told me I could only get Skittles from the pool concession stand if I ordered them myself, I would just skip the Skittles that day.

Eventually I got over it and was involved in a lot of extracurricular activities, which taught me a priceless lesson in time-management. I mostly did the extracurriculars at school for the social aspect, because I am definitely not an athlete in the traditional sense. My true passion was riding horses. I begged for riding lessons for about three years until my parents finally caved. They thought/prayed it was a phase, but I’m now 43 and it’s still a huge part of my life.

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