Case Study

Head of BD to CEO in 5 months

Digital Third Coast

“If you’re not showing up for your business at 100%, you’re already costing your business more than you’re going to spend on working with Brad. I definitely was.”

~ Lyndsey Maddox
Lyndsey Maddox

Digital Third Coast (DTC) is a Chicago-based digital marketing agency specializing in SEO and Paid Media. DTC was founded in 2007 with a mission of making a measurable difference for every client. For nearly 20 years, DTC has helped coffee retailers, universities, hospitals, and everyone in between increase their visibility and authority, find new leads, and grow their revenue. This team is comprised of problem solvers and data nerds, and they’re regularly recognized as one of the best digital marketing agencies in the country. 

How did you first meet Brad?

I knew Brad peripherally for about a decade before calling on him for help. 

In the winter of 2023, I was feeling stuck. I’d been in the same role—Director of Business Development—at the same agency—DTC—for 11 years, and I felt like I wasn’t leveling up. I needed advice (or maybe just a kick in the ass). So, after running into Brad at a networking event, I emailed him and asked, “Do you ever work with non-founders? Specifically, will you work with me?” 

I’ve always told Brad that I should be his case study, because I emailed him in February asking for help, and by July, I was CEO.

What did you set out to accomplish? And, what were some of the biggest takeaways from your work together?

At the time, I was trying to figure out what I wanted to be when I grew up. I don’t know that I’ll ever completely answer that question, which I’m coming to terms with, but Brad helped me shift from constantly asking myself “What am I going to do tomorrow?” to instead asking “Where do I want to be in a year?” 

We outlined business goals and personal goals, and, rather than thinking about these as two totally separate things, we talked about how each could support the other, because when you’re running a small business and running a home (I have two small children), everything is everything, and you can’t do it all at once. 

One of the biggest things Brad helped me practice is being present for what’s in front of me. It sounds simple, but it isn’t. For too long, I’d been trying to do everything all at once, wavering between the grandeur of ego (I can do it all!) and complete imposter’s syndrome (can I do any of this?).

How often did you meet, and what did the work sessions look like?

Working with Brad is essentially business therapy. We met every couple of weeks for about six months. Some days we role-played conversations that I needed to have with colleagues, some days we talked about articles I’d read (there was always homework), and some days I’d walk into our session and say, “I know we planned to talk about X, but I’ve got a whole new problem for us to solve.” Brad’s approach is structured but agile—he’s always game to shift gears when needed.

Your favorite thing about working with Brad?

His laugh. I’m sure Brad has a whole life outside of work, but the way he shows up for clients is so supportive and focused. Brad shows up in a way that makes me better at how I show up. It’s way beyond a P&L conversation.

Can I tell you a quick story? Not long after being promoted to CEO, I was diagnosed with cancer. I got the news on a Wednesday morning and immediately started rescheduling my afternoon meetings. But I didn’t cancel my meeting with Brad. Instead, he was one of the first people I told. That morning, I shared how overwhelmed and lost I felt, and together we started sifting through everything that needed to be in place for me to go on leave. 

The fact that I didn’t even consider canceling our meeting that day tells you everything you need to know about working with Brad.   

If you had to describe your experience in just three words?

Valuable. 

Reflective…or educational? These words feel too small for what I’m trying to say, but I’ve learned so much from working with Brad. 

And, the third word: necessary. For me, it was necessary. Not a “nice to have”—“a need to have.”