Today we’d like to introduce you to Heather Monahan.

Heather started from very humble beginnings growing up in Worcester, Massachusetts. After graduating from Clark University, she began her career in sales and quickly advanced to a top salesperson and Brand Manager within her first year in corporate America. After being harassed in her position, she left the wine business and started working for Wilks Broadcasting as a salesperson in radio. A year later, she was offered an equity partnership which required her to move to Saginaw, Michigan.

Heather made the difficult decision to leave her family and friends behind and move alone to the Midwest for the chance to create value and potentially sell the Saginaw properties for a gain. Within three years in Saginaw, she significantly increased the group’s value resulting in a successful sale of the properties more than doubling the purchase price from 27M to a final sale of 55M. Heather then moved to Naples, Florida to begin working for Beasley Broadcasting where she started as a Director of Sales.

After one year of substantial revenue results, she pitched herself for a position that didn’t previously exist and was awarded the VP of Sales title for the company. Over the next few years, she pitched herself for and was awarded the newly created EVP Sales position and ultimately the Chief Revenue Officer title.

During this time Heather launched her personal brand to empower women and give them the insight and tips she had longed for as a young professional. She was the Keynote speaker at the Corinium CRO conference and held the main stage at the LOAC in NYC. Heather was recognized as a Glass Ceiling Award winner and as one of the Most Influential Women in radio in 2017 before her unexpected termination.

Faced with the choice to go back to her comfort zone or take a leap of faith and pursue her passion to elevate others, Heather chose to make her company Boss In Heels her full-time job. Over the next few months, Heather was featured on the Elvis Duran show, she completed her first book entitled Confidence Creator and was named the Brand Ambassador for Perry Ellis International’s female brand Rafaella. Heather and her son Dylan reside in Miami, Florida.

Great, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?

No, it has not been a smooth road at all! My struggles ranged from being sexually harassed at work to being bullied by another woman. My personal struggles were getting divorced and holding myself back because of a lack of confidence. The best advice I can give any woman is to focus on building her confidence and putting herself first. Firing negative people from your life and surrounding yourself with positive people that want to help you grow will ensure you take off. Being mindful of the words we use about ourselves and choosing powerful words that we want others to use when describing us will help the way others perceive us. Getting rid of phrases like ‘I am sorry’ and ‘I feel’ will put us in the driver’s seat. Learning to take fear on like a game, will get us out of our comfort zone and into a growth phase. Keeping a journal has been a fantastic way for me to see my own strengths and identify my superpower, I recommend it to everyone! I have countless tips and stories in my new book, Confidence Creator that will help anyone build their Confidence muscle.

Please tell us about Confidence Creator.

I am currently hyper-focused on the launch of my new book Confidence Creator and it consumes most of my time. As a first time author, I found myself as a beginner again at age 43, which has been a challenge. Learning how to create my own publishing company has been another mountain I have had to climb. After a successful career in corporate America, I took the biggest leap of my life when I started my own company Boss In Heels. In my previous career, I was known for leading sales teams and developing corporate strategy, now, I take all of the experience I have obtained and I share it in order to elevate others. I have a very unique background in achieving success in sales and in business and I share that knowledge along with my own personal stories to ensure others see how they too can get ahead. I am most proud of my new book Confidence Creator and the fact that I wrote it in 4 months and was able to publish it on my own in 5 months. Taking risks is the only way I have ever grown and this is the biggest one yet. I am so different than others because I am transparent and anyone that has seen me speak will attest to this. I am committed to keeping it real in a world that is full of filters and fake images which isn’t always easy.

Often it feels as if the media, by and large, is only focused on the obstacles faced by women, but we feel it’s important to also look for the opportunities. In your view, are there opportunities that you see that women are particularly well positioned for?

Every woman has her own strengths and superpower and the key is identifying what yours is and finding a way to spend your time there. Because of the strong women that have come before us, there is finally a tide turning and shining a light on pay inequality, sexual harassment, and bullying. It is up to each one of us to continue to find our voices and shine our lights so that others after us will have it even better. I believe that right now is the time for women to own their superpowers and take chances on chasing their dreams, there hasn’t been a better time.


  • Hardcover Confidence Creator 24.99
  • Paperback Confidence Creator 15.99
  • Kindle Confidence Creator 6.99
  • Audio Confidence Creator 15.99

Contact Info: