My Journey to Leadership: Meet Kyle Evangelista, President and Group Publisher

by Cristina Merrill

Guerrero Media President and Group Publisher Kyle Evangelista had a fruitful teaching career before he found his way back to Chicago and to our organization. But by the looks of it, his days as a teacher and mentor are far from over.

Where are you originally from and what is your background?

I was born in the Chicago suburbs, specifically in the Wheaton/Glen Ellyn area. I went to school at Loras College in Dubuque, Iowa, where I studied secondary education. After graduation, I taught economics, sociology, history, and more in American international schools around the world.

How did you first come to work for Guerrero?

I moved back to Chicago after teaching abroad for six years and decided teaching wasn’t for me.

When I returned to Chicago, I had a number of interviews, but no one gave me a job. Guerrero was the only company to give me a job offer, and so I took it. I started in 2013 on [our architecture brand] American Builders Quarterly. My first boss was Titus Dawson; I learned countless lessons from him, about what to do as well as what not to do, by watching him work. He is a close friend of mine to this day and has returned to the company after a stint elsewhere: he is now part of the great team he helped build many years ago.

What do you do at Guerrero today?

I am the president and group publisher of Guerrero Media. My main responsibility is ownership of the core engine: sponsored content sales, trafficking, and publishing. It’s vital to support the leadership team, and entire company, by uniting the cross-functional teams that are responsible for sales, editorial production, and client services.

My journey to this point in my career hasn’t been quick or easy. It has been plagued with potholes and failures: I have had to hold on tight, jump, and press on through. It has also been filled with a plethora of incredible moments that have defined not only my professional life but also my personal life.

In summary, my journey to leadership wasn’t glamorous, and I don’t think it is for anyone. But I had patience and confidence in the company and its leader. I put in the work and made a ton of sacrifices that the average person would never make to advance in their career. I remained grateful for every string of luck I hit, and I remain forever indebted to the people who did and who still are picking me back up after I fail.

How would you describe your leadership style?

I think I’ve read enough 360 degree surveys that describe my style—the good, the bad, and the ugly!—that I can say I’m incredibly confident in my ability to execute. I’m fearless and forward-thinking. I believe in cutting through the noise and being direct and to the point. I will also admit that I have high expectations and can be harsh and even too negative at times. But it’s ultimately because I’m deeply passionate about the work we do here at Guerrero.

How have you maintained a connection with your team during the pandemic?

We’re all human, and I feel like many relationships and connections have faded due to the situation we’re all in. Do I maintain a connection with my team? Obviously. But it is harder to [achieve] a level of authenticity and consistency with remote relationships. That being said, I do believe in the age-old saying, “Absence makes the heart grow fonder.”

How has Guerrero evolved over the years? What’s the most marked difference from when you started?

Well, I started in an office that we had just moved into, and construction was everywhere. I literally interviewed for the job in the middle of a kitchen that had no refrigerator. So, the most marked difference is that now we have a refrigerator and walls!

In all seriousness, looking at the evolution of the business is incredibly similar to looking at my own evolution.

Everyone is familiar with those kinds of moments when you look back to the decisions and how you went about them five to ten years ago. Some of them are cringeworthy, right? Other decisions and how we went about them look absolutely genius. It’s the ever evolving cycle of learning through doing and adjusting through reflection. There is no button to press to fix anything. The correlation I have made is that most evolution within our business and my own personal life comes with the understanding that everything worthy of doing, creating, and changing requires constant grooming, each day. This is the level of commitment it takes to truly evolve something.

What makes Guerrero such a great place to work?

Honestly, giant corporations that pedal “perks” just aren’t for me. I don’t care about kegs in the lunchroom or the napping pod room. I care about transparent leadership, being required to think critically, working with talented people who have the same level of commitment and belief in the company as I, and being given the opportunity to earn a killer paycheck by delivering great results.

What do you like to do when you are not working?

I’m finishing up book number one in a series of books I’m writing. The first book is for young professionals entering the workforce. I just tell my story and share the experiences I’ve been through and what I see today. The second book in the series will be for first-time managers. It will be about what I, and others, have learned from doing and observing every day.

I also enjoy spearfishing and cooking anything Italian. Each year, I’m getting closer to mastering my grandmother’s cookbook.

What else would you like to share about yourself?

I recently got a fantastic new Breville coffee machine. It’s seriously life changing!

My wife is from Mexico, and my son lives in France. My wife and I just had a baby girl, Isabella, who is seventeen months. We have a very international family, and I’m thinking about publishing a cookbook that contains a mix of my wife’s Mexican recipes and my Italian ones.