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. In three years Heather significantly increased the group’s value, 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.

Heather then moved to Naples, Florida for a Director of Sales position with Beasley Broadcasting. 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.