I Sucked as CMO. Here's Why I Gave Up My 'Chief' Title to Do What I'm Actually Great At I stopped chasing a title and built a role that truly fit me.
By Jake Karls Edited by Frances Dodds
This story appears in the July 2025 issue of Entrepreneur. Subscribe »
At first, I really thought I needed a big title.
I cofounded Mid-Day Squares in 2018 with my sister and her husband. They'd created our product, which is a chocolate afternoon snack with protein and fiber. So they became co-CEOs (they're awesome operators).
I took the CMO role because it felt important and had "chief" in the name, and because, frankly, I was really good with social media and building community.
But as soon as our company started to grow, I began to fail. To understand why, I needed to ask myself some big questions like: What is my actual value? And how can I best put that to use? These days, I'm so much happier and more effective — and I'm no longer CMO. I think other founders would benefit from asking themselves these same tough questions, and making hard changes.
Related: The Four Steps to Creating Lasting Change in Any Area of Your Life
Here's how it all started:
At first, Mid-Day Squares was just us three cofounders. We moved fast and had fun. Then we started scaling and hiring quickly, and I had to manage new team members. I suddenly struggled to make decisions. I couldn't articulate my ideas to my team, so instead, I just started executing things myself — without telling anyone.
As a result, my team was confused. Other departments were annoyed. Eight months in, I wondered if I should even be part of the company anymore.
Then my cofounders and I made a critical decision:
We would talk about this with our therapist.
The therapist was part of an early commitment we'd made to each other to protect our family and professional relationship. We went to group therapy every week, and it helped us navigate hard problems and think through large risks. But I hadn't really brought up my struggles as CMO...until that moment.
As we discussed it together, I realized that I was in the wrong position. I loved the ego boost of being CMO, but I was a bad fit for the role. A CMO needs to inspire, craft a vision, and execute it. I wasn't good at that.
If I was honest with myself, I didn't even want to be CMO. But giving up the role felt like failure — so I fought it. I told myself to push harder. I tried to force it. It took a lot of therapy sessions, tough conversations, and real self-reflection to finally decide that I needed to step down.
Then I had an even bigger question to ask: What do I do instead? While we were in therapy, my cofounders gave me an answer: "Find your superpower, and let's create a position around it."
So I started to explore. I'm bubbly and magnetic, and that's where I shine. I love building relationships and emotional connections, creating and spreading energy, being bold, and making noise. So in 2019, we created a new title for me: I became the "Rainmaker."
Now I spend most of my time traveling, meeting people for dinners, going to events, building networks, speaking at conferences, and appearing on podcasts and TV. As a result, I've brought all kinds of people — investors, retailers, consumers, new recruits, and media — to the company, equipping each department with key external relationships so they can win. That's helped us go from making 50 squares a day in our small condo kitchen to producing over 130,000 in a day in the factory we built, selling over 55 million of them. Our retailers now include Target, Whole Foods, and Sprouts Farmers Market.
My cofounders and I still attend therapy together. Some other team members have followed suit. And we all now understand: Leadership isn't about titles. It's about having the courage to pivot and lean into what truly makes you come alive.
