Caitlin Gayles

(Christopher Newport)

The Educator | 40 Under 40 Class of 2020


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    Coasta Rica


Thoughtful, authentic and determined – that’s Caitlin Gayles. She currently resides in Denver where she is a schools manager for an education company that creates quality supplemental resources for teachers across the country at no cost. She unpacks everything from her upbringing to her collegiate years to her professional accomplishments in her extended interview. Check it out!



What inspired you to go into this line of work?

Since I was a kid, my family has really stressed the importance and impact a good education can have on your future. I’ve seen it in my own life and the lives of others, so being able to work for organizations that create accessible and quality education opportunities is very important to me.


What challenge did you overcome to get where you are today?
A challenge that I have overcome but continue to work on is moving past that little voice in my head that says you can’t. I think as a woman, and as a woman of color especially, I grew up thinking and hearing there were a lot of things I couldn’t have or couldn’t do because I didn’t see women who looked like me doing them. For me, each day I try to remind myself that I can, and I will.

Did someone help you get to where you are today, like a mentor?

Honestly, it takes a village. I can think of so many people throughout my life that have cheered me on and steered me in the right direction. Here’s a few off the top of my head.


  • Mr. Demek, my high school AP history teacher who recommended that I investigate professions that had a public speaking component and showed me that my voice had power behind it.

  • Jenny Dean, the absolute angel was was my chapter advisor throughout my time as an undergraduate in Gamma Phi Beta. When I became president of my chapter, Jenny was there for me every step of the way and she gave me the confidence and push I needed to be a leader.

  • Katie Litle-Wellbrock, she helped me immensely in my first “real” job. She didn’t just help me figure out what was next in my career but also as a person. Katie is so incredibly fierce, and she presented a level of career confidence that I will always hold as my standard. She walked into rooms knowing she was supposed to be there, and it really resonated with me. 

  • Through it all though, I have to say my dad. He is my life advisor and the person I turn to before I make any big decision.

What do you love most about your job?

The facetime I get with students! I have the opportunity to travel all around Colorado and go into classrooms and meet incredibly bright students. It reminds me every day that there is a new opportunity for impact.

Early Bird or Night Owl


Mountains or Beach


Cats or Dogs


Left Brain or Right Brain


Stripes or Polka Dots


What do you love most about your job?

The facetime I get with students! I have the opportunity to travel all around Colorado and go into classrooms and meet incredibly bright students. It reminds me every day that there is a new opportunity for impact.


Describe yourself in three words.

Thoughtful, authentic and determined.


Your life philosophy is…

Reflection is the key for growth. I think it is important to stop and give yourself time to process what goes on in your life. A lot of time we endure the day, sleep and do it again. We should think through what we go through. It has helped me recognize my strengths, weaknesses and values.


What is the best piece of advice you received?

From my dad, a retired lieutenant colonel in the U.S. Army: Always have a plan.

If someone handed you an airline ticket to a place of your choosing, where would you go and why?

At this exact moment, I would say Patagonia in Argentina. It looks unreal.


What’s something you cannot live without?

This question is so hard! Ultimately, friendships. Life can be so tough; it is important to have people in your corner.


Name a book you read that positively shaped you.  

“The Defining Decade” by Meg Jay. It was a book that reminded me that life is short and that your twenties can be this opportunity to shape the rest of your life. It gave me the motivation I needed to challenge myself in my career and my relationships.


If you weren’t working in the industry that you are, what would you be doing instead?

If someone would pay me to travel to beautiful places and eat all the food, I would do that. Realistically, if I wasn’t working in some facet of education, I would probably do something that relates to public speaking.


How do you unwind or relax after a long day?

Hot bath, good playlist and a great cocktail.


The most rewarding aspect of your job is…

Seeing students get so excited to learn about topics I never thought about in school, like nutrition, STEM, banking basics, etc. Also, knowing that they can learn those topics at no cost to them, their teacher or their school district.


If you could have a gigantic billboard anywhere with anything on it – metaphorically speaking, getting a message out to millions or billions – what would it say and why?

“Just try.” Life can be intimidating sometimes, and comfort can keep you in a place where you are not growing personally or professionally. Over the past couple of years, I’ve encouraged myself and others just to try jobs that seem out of your league. Just try and apply. Can’t run 13.1 miles? Just try to run two. We often stop ourselves from pursuing growth because we are afraid of what could be on the other side, but it is important to simply try.

In the last five years, what new belief, behavior, or habit has most improved your life?
You can’t control everything. Once I started letting go and just letting things happen, a lot of my stress went away.


When you feel overwhelmed or unfocused, or have lost your focus temporarily, what do you do?

If I need a quick solution, I will go outside and take a 10-minute walk with a lot of deep breaths. If I have a little bit more time, I’ll go workout! It helps me get out of my head.


What is one of the best or most worthwhile investments you’ve ever made? (Could be money, time, energy, etc.)

Investing in my physical and mental health. In college and my early twenties, I ran myself ragged and treated my body like garbage. I was giving my mental energy to people and things that did not serve me well, and I had crippling anxiety. I saw a therapist, started exercising regularly, eating better and began saying no. It was life changing. I finally felt like I had developed a personal toolkit to keep myself in check and healthy.

Name a confident woman of character who you look up to? Why her?

Michelle Obama. I think she is a phenomenal combination of wit, grace and unbridled optimism. She has used her voice to empower women and girls across the world.