“If you know how to sell…you will always have a job”. Meet Cheryl (27/52.2)

Meet Cheryl:


In her own words -


"My dad always told me I could be anything I wanted to be in business; gender was never a part of the conversation. He is a natural speaker, salesman, gifted writer and was a successful adverting executive in what is known today as the “Mad Men” years of advertising. So when it came to career paths, there was no judgment from him, just unconditional support. When I did graduate college however, my dad told me “If you know how to sell…you will always have a job”.


Cheryl with her father as a child and with him now - ©Amy Boyle Photography 2020

Sales? There was no degree in it, no formal training, no career path; and at that time, it was not a line of work women aspired to. Sales was surely not what one would say when asked “what do you want to do when you grow up?”


So, as I took my college degree, my high school years of theater experience and my  ‘gift of gab’ to the Help Wanted section of the newspaper (there was no internet, no Linkedin, no ‘click and apply’), I got my first job at The Chicago Sun Times doing outside sales for their automotive advertising department. I sold print advertising to big car dealers with big cigars, often asking from their showroom floor, “What’s a girl like you doing selling auto ads out here?” And it was there that I found that I not only enjoyed the challenge of creative selling and connecting with interesting people, but realized I also enjoyed being paid based on my own efforts and success. As a side adventure, I also signed up for Improv classes at Chicago’s Second City; and it was there that a fellow performer (who happened to be a radio sales manager) hired me to take my sales (and Improv skills) on to the stage of Radio Sales. With no training and just a phone book for leads, I was back doing door to door creative sales. It was the beginning of a phenomenal 30+ year career.


With incredibly talented leaders helping me along the way, I rode the wave of some of the very best years of the radio industry. I got to work with big personalities and sports teams at the infamous Loop, selling programs such as Jonathan Brandmeier, Steve Dahl, The Chicago Bulls, Blackhawks and more. It was a job filled with concert events, major sports team outings, celebrity sightings and one that was filled with excitement every single day. Radio Sales was THE place to be in those days. I learned how to survive and grow my career amidst endless management shuffles, ownership changes, format adjustments and even heard about getting another new boss while in my wedding reception line!


©Amy Boyle Photography 2020

Moving up the ladder from salesperson to manager to Regional VP, sales gave me the platform and the stage to tell stories, win customers, coach young people who were new to the field, build lifelong relationships, and lead teams to success.


I never could answer the question “Where do you want to be in 5 years” because I was already ‘there’, for my entire ride. Not by design, not with a strategic plan, but by simply doing what came naturally; talking, connecting with people, a touch of humor, a bit of Improv, and leading a team to do the same.


Becoming a mom, and keeping that job front and center, along with my radio and now TV career with Weigel Broadcasting, continue to be simply the best jobs of a lifetime.


©Amy Boyle Photography 2020

If we are lucky, we get to use the gifts we are born with to build a fulfilling career. I look forward to continuing to lead, coach and mentor the next generation of professionals, helping them turn their unique gifts into a lifetime of accomplishments.  Thanks, Dad!"


*** Please follow along on instagram as well and learn more about Cheryl52 Phenomenal Women is now in its second year! This is week 27 of 52.


Participants in this project will be supporting the efforts of Dress for Success Worldwide – Central. We are all stronger together and it is my sincere hope that we will be inspired by each other’s stories. Now is the time to celebrate as well as encourage one another. Tell your story!***


©Amy Boyle Photography 2018 - 2020 All Rights Reserved

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