Jill Gutierrez | Crain's Twin Cities

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

Jill Gutierrez


Sightly is an ad tech company that helps media buyers use YouTube more effectively. Sightly’s new Los Angeles office will be overseen by Jill Gutierrez who has more than a decade of experience in media and advertising, and has guided marketing initiatives for Nissan, Jiffy Lube and Wells Fargo. 

The Mistake:

Early on in my career I thought everything had to be perfect, I had to know everything and I had to have a plan.

I was at AOL for almost seven years and I wanted to leave because I knew that I was [too] comfortable and I wasn’t learning anymore. So after AOL, I went to another company and while it was a great move, it was an experimental change.

I was helping set up a strategy and basically the structure of the team, and in doing so I realized the overhead was too high. I wasn’t planning on leaving but then I had an opportunity present itself and I ended up taking it and leaving.

However, I think I should have probably not left. I don’t know if I would have been laid off or not, but I wish I would have stayed instead of leaving. I wish I would have seen how it would have progressed and played out. 

It’s OK to learn as you go.

The Lesson:

I’ve come to realize that as a part of going through your career, it’s important to educate yourself.

Without taking risks, or even failing, you’re not going to learn firsthand. It’s OK to learn as you go. I think that’s been the biggest realization. You don’t have to know everything. It’s impossible to know everything.

You will disappoint people, you will let people down. Nobody’s perfect, first and foremost. Stop agonizing over making mistakes, because sometimes making mistakes can be very educational. Sometimes a mistake will be the best and biggest lesson you’ll ever have.


Follow Sightly on Twitter @SightlyHQ

​Photo courtesy of Sightly. 

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