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Heather  Monahan

Heather Monahan

Best-Selling Author, Entrepreneur & Founder of Boss In Heels


Heather Monahan is the embodiment of a powerful woman in business. She began her career in sales and quickly advanced to top salesperson and Brand Manager within her first year in corporate America. A year later, she began her career in the broadcasting industry and joined Wilks Broadcasting as a salesperson in radio. Within a year, she was offered an equity partnership which required her to move to Saginaw, Michigan. Read More >

Heather made the move 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. Within a year of creating 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. A few years later, she pitched herself for and was awarded the newly created Executive Vice President of Sales role and ultimately the Chief Revenue Officer title. While Chief Revenue Officer, Heather oversaw the entire sales organization and led the group through multiple acquisitions and product additions yielding a successful merger doubling the top line revenue. During this time Heather launched her personal brand to empower others 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 2017 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.

In late 2017, 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 and the Morning Show, wrote and self-published her first book entitled Confidence Creator and was named the Brand Ambassador for Perry Ellis International’s female brand “Rafaella”. Subsequently, she was named a limit breaking female founder by Thrive Global. She is also a member of the Florida International University (FIU) Advisory Council to further serve as a mentor and leader in the South Florida community.

Heather was the keynote speaker at the 2018 Entity Women’s summit, the mistress of ceremonies for the Miracle Makers 60th anniversary Big Brothers Big Sister Luncheon and fashion show and was the Keynote speaker for the S.H.E. Summit Bacardi this September. Since her book launch she has also delivered the Keynote for Horizon Media’s Limitless group, iHeart Radio Miami and Las Vegas, Entercom Miami, MGM Las Vegas, Zenith Media’s Blue 449 in addition to the Aces night for the WNBA. Heather’s 2018 speaking engagements also included Royal Caribbean, BNY Mellon, Greenburg Trauig Law Firm, Boise University, FIU, University of Miami Business School, Miami Dade College Honors School and Miami Dade College Innovation group in addition to Worcester Academy where her book has been added to curriculum. In 2019, Heather was tapped to speak at Harvard University.

Confidence Creator was released on Amazon May 22nd and immediately took the #1 New Release in the categories of Business Motivation & Self Improvement, Women’s Personal Spiritual Growth, Self-Esteem, & Personal Transformation. Before the end of the first week Confidence Creator claimed Amazon’s #1 Best Seller in Biographies of Business Professionals, Women’s Personal Spiritual Growth and Personal Transformation. Heather has been featured in USA Today, Bloomberg, CNN and various other media outlets for her work to elevate others.

Heather Monahan grew up in Worcester, Massachusetts and graduated from Clark University. Now, Heather and her son Dylan reside in Miami, Florida. Read Less ^

Speaker Videos

Speaking Reel

On Overcoming Fears

Confidence Creator Promo

Find Your Superpower

On Steve Harvey Show

Speech Topics

The Game Changing Power of Confidence Creation

When you are your most confident, you share your ideas, embrace collaborating with others and contribute your ideas in meetings. Confidence is the one thing that changes everything in any environment. As setbacks and challenges are destined to occur, those who are confident withstand the blows while others crumble under the pressure. Read More >

Lacking confidence typically results in an inability to get promoted, get noticed or even be heard. The feelings of frustration, disappointment and anger that go along with lack of confidence can be debilitating. Lack of confidence leads to a life of existing instead of thriving. Even though it is clear that everyone wants to be confident, most people and companies do not have a plan to create confidence for the individual and within the workplace. As a result of lack of confidence there is a lack of revenue, lack of innovation and lack of collaboration.

There are often culture issues throughout organizations of blame and lack of trust when confidence is absent. Luckily, it doesn't need to remain this way. There is a solution.

Heather Monahan has spent the last 24 years developing her strategy to create confidence, overcome challenges and step into your power. Heather will share with you her direct, systematic approach to create change for the individual and organization. Heather's unique approach of sharing her personal low moments allows the audience to engage and relate quickly. Learn how to create confidence in yourself and get ready to take yourself and your organization to the next level now. Read Less ^

The Life Changing Difference: Becoming a Confident Woman

Lacking confidence as a woman is something Heather Monahan knows quite a bit about. Feeling less than others, feeling scared to put yourself out there or just feeling lost are all signs that it's time for you to create your confidence. Beginning as young as 8 years old, females statistically report having less confidence than their male peers. Realizing that the gender pay gap isn't closing anytime soon, it is time to take charge and create your own confidence so you don't have to wait for the invite and instead create it for yourself. Read More >

The majority of women today are struggling with self-doubt. Most women fail to put themselves first. Many women are bullied and don't know how to stand up for themselves. Our culture applauds men winning awards and sharing the news yet a woman feels petrified to share the news of her accomplishments. Women are afraid to appear "mean" or "full of themselves" and most women accept the blame for things they are not responsible for.

Ending the constant apologizing, self-deprecation and need to play small, will create confidence and set women up for opportunities they currently don't see as possible. There is one opinion in this world that matters and it is yours. It is about time for you to own it and shine your light so the rest of the world can see.

Heather Monahan is the speaker that will bring her real-world experience and share her personal heartfelt stories to your audience to empower them to create change and elevate them for life. The specific steps that Heather will share with your audience will leave them fired up and ready to take the leap to create their own confidence and make change in their life for the better. Sharing her hard-won wisdom with your audience will equip them with the tools, understanding and inspiration to make the changes needed. Confidence isn't given, it is created. Heather's unique journey of shattering the glass ceiling in corporate America, building millions in value and being fired only to reinvent herself as an author, speaker and entrepreneur will connect with your audience like no other woman can. Read Less ^

The Revenue Recipe: Creating the Confident Sales Team

In every exchange someone is sold. Whether it is you being sold to pick up your friend’s dry cleaning or you selling your friend as to why you can't do it and instead doing something for yourself one of you will ultimately sell the other. Becoming your most confident self will free up time for you to care for yourself and do things you want to do. Creating your confidence will empower you to become the "real" you, the one that you had been afraid to be. Taking off the mask of who you thought you had to be and instead owning who you are will allow you to communicate and sell in ways that you never knew were possible. What makes you unique and different is where your superpower lies. Once you have discovered your superpower, achieving your goals and increasing sales is easy. Read More >

After more than 20 years driving sales and leading teams, Heather Monahan will share the ways she became a top producer and grew hundreds of millions in revenue. Heather does not teach the old process of selling instead she brings a fresh perspective to work that empowers your people to step into their confidence and finally see what has been holding them back from achieving their success. The relatable stories that Heather brings to your team make the lessons memorable and impactful yielding results. If you want to set your sellers up for the biggest year of their life and your company's biggest revenue spike yet, create confidence for your sellers and your team. Heather Monahan is not only an expert in sales she is also an expert in confidence creation and combining her expertise delivers a presentation you can't afford to miss. Read Less ^