Kayla Sanders | Crain's

In this ongoing series, we ask executives, entrepreneurs and business leaders about mistakes that have shaped their business philosophy.

Kayla Sanders


Remy is a cloud-based management software for health plans that deal with Medicare, Medicaid and the health insurance marketplace.

The Mistake:

I worked for a large management consulting firm when I was 24 or 23. I was still young, passionate and fiery. I left a project in St. Louis and headed on, finding my next opportunity out on the East Coast. It seemed like a perfect fit for my skill set and a perfect fit as far as growth opportunities for my career. I was hungry, I was ambitious, I was used to working seven days a week, 24 hours a day — and I was ready for the next challenge.

I got there to find out that it was absolutely not as advertised. The scope of what I was going to be asked to do was a lot more mundane and routine. It just wasn’t challenging. I really like something that can make an impact, rather than just managing day-to-day tasks.

I am the type of person that if I'm not challenged, I get complacent. I was clearly unhappy, and I wasn’t great at not showing that.

Leadership would ask me, " Why aren't you engaging? Why are you so quiet? Why aren't you participating?" But I was too stubborn to discuss my feelings with them.

I thought, "Maybe, I'll give it a week. Maybe two weeks. Maybe something will change." And that didn’t happen. So my frustration grew. I was working, but it was just so hard for me to get engaged.

So I went to a senior leader — a partner at the firm — and said, "This isn't what I signed up for, this is a misuse of my skill set."

The partner responded, "Who are you? When did you decide you were going to tell us what to do? You need to learn to work better in a team."

Know your worth, know your strengths and stand up for that in the right way.

The Lesson:

That was my turning point, that corporate America might not be the right fit for me. It restricted me. I had to play by these standard set of rules, inside the box, and that’s never been me. It was important to learn early on where I fit and where I could best optimize my talents and grow.

I could have handled myself differently though. I was happy that I was vocal, but I also was a little passive-aggressive. Know your worth, know your strengths and stand up for that in the right way — I could have done that better. You can’t let your emotions get the best of you. It’s not personal; it’s just business.

Follow Kayla Sanders on Twitter at @KMaree_Sanders.