Heather Monahan is a women’s empowerment expert known as the “Boss In Heels”. She is a social media influencer, keynote speaker, Glass Ceiling award recipient and Pop Sugar contributor. Heather is committed to advancing others via www.heathermonahan.com and through her recent appointment to brand ambassador for Perry Ellis International’s female brand, Rafaella.

What motivated and inspired you to start your own business?

Growing up poor, I had limited access to resources and mentors. Through sheer hard work, I muscled my way to the C-suite in media. What I realized once I got there was… it didn’t have to be so difficult.

Unfortunately, I had never had a female mentor along the way to help me and teach me the tips that I needed to advance so I took a much harder route. Most successful women (that I encountered in business) were fake and cold and more concerned about holding women back instead of mentoring and advancing others.

I realized that other women must be in the same situation that I was in. I became dedicated to sharing my insight and offering the same mentoring that I provided for the people that once worked for me for others.

How it Began

Tell us about your business.

Up until a few months ago, I was the CRO for a radio company and had launched my website and social initiative to empower women outside of work. After 14 years at this company, they decided to eliminate my position and I found myself fired for the first time. Having a non-compete in place, I was prevented from going back into the media business to earn income.

As a result, I decided to launch my own company, Boss In Heels, and take the biggest risk of my professional life. What had started as a passion project that I worked on at night and on the weekends suddenly became my full-time job. While I have been a speaker for years, I now speak for myself and my company on topics that are interesting and meaningful to me.

I have spent the past few months writing my book about how to build confidence and leap frog the villains you meet along the way. I also have collaborated with a number of different companies on various partnerships and most recently partnered with Perry Ellis as their Brand Ambassador for Rafaella.

Our goal is to empower women through our clothing and through the tips and tricks I have learned along the way. My business is evolving daily, and there is tremendous opportunity for growth when you lean into a space that you are passionate about.

I still mentor and work with women on a one-to-one basis when time allows since it always feels so rewarding, as well as helps me to stay focused on the real issues we all face each day.

Are you currently running any promos/contests/giveaways that you would like our readers to know about?

During the month of February I will be picking one winner to give a private coaching session to. Follow me on social media to get a chance to win!

Private Coaching Session with Heather Monahan

List awards/certifications/accomplishments.

  • The Glass Ceiling Award 2015
  • The Most Influential Women in Radio 2017
  • Keynote Speaker Women’s Empowerment Expo Ft. Lauderdale 2016
  • Keynote Speaker Corinium Global CRO Conference 2017
  • Keynote Speaker LOAC NYC 2017

Where is your business based?

Miami, Florida.

What were the first few steps you took to get your business up and running?

Luckily for me, I had begun investing in building my personal brand a year and a half before I was fired from corporate America. By investing in myself I was able to elevate my profile beyond my limited radio world I was living in.

Through doing this, I was able to rapidly grow my business network and connect into new industries that I had previously ignored. I made a significant financial investment in myself at that time and I was petrified. That time was very difficult as I was getting negative feedback from my employer and my decision to not back off and instead continue to pursue my passion outside of work is now giving me the life and livelihood I always dreamed of, but never knew was possible.

Discovering what your own superpowers are and marrying those with your passion will yield where you should truly be to find happiness in your work. Just because you are good at something doesn’t mean that is all you should ever do.


How it Grew

What has been the most effective way of raising awareness of your business and getting new customers?

To me, partnerships are the most important business venture. Continuing to invest in my personal brand and leaning into media outlets to get exposure has paid major dividends. I started small by accessing the local paper and this led to bigger opportunities with outlets like USA Today and Fast Company.

The key is starting somewhere and not give up. I also have used the site Help A Reporter Out and have found some great opportunities through their offering. In order to raise your awareness, you need to put yourself out there publicly and take chances that aren’t always easy. Defining what your expertise is and creating content around that topic will always pay dividends.

What have been your biggest challenges so far?

The first year I launched my brand was one of the hardest because of the negative response I received from my previous employer. Distancing myself from that negativity has been fantastic, but it brought on new pressures instead.

Having no control over other companies when I am trying to get things approved as an outsider has been difficult. I often feel that the only thing I have going against me is time and I am working on mindfulness and patience while continuing to push the envelope daily to overcome it.

My challenges are constant and always evolving, but doing what you love and working for yourself makes it so worthwhile.


How did you overcome these challenges?

The negativity from my previous employer took care of itself when they fired me. Suddenly, the negativity in my life was gone! Having no control over the speed at which a partner moves can be challenging, but it also challenges me to find new ways to interest them to move more quickly. Working with new companies where I don’t have a long-standing relationship and partnership in place meant I needed to build credibility and trust in order to gain their confidence.

This reminds me of when I was younger just breaking into business, and I had to dust off that old talent and put it back into motion to be successful. Business is so much like riding a bike in that there will be constant change and times where you need to access a skill that you used in the past.

At first, it is hard to adapt to it, but with time it becomes second nature. I like watching myself go through these phases and come out the other side. Knowing that time is the one thing I have working against me keeps me driven like nothing else.

I recently was in an Uber in between meetings and I was fielding different calls. When I got off the last call the driver told me that he wasn’t sure exactly what I was working on, but he had no doubt I would succeed because he had never heard someone so driven. That comment really resonated with me, and showed me sometimes we don’t see what is so special about ourselves until someone else sheds a light on it. 

How do you keep motivated through difficult times?

That is the motivation! If everything was easy than everyone would be doing it. Knowing that if things are difficult I have a choice each day to give up or to go forward and find solutions. I am not a quitter so for me staying motivated is the only option.

It also helps me to remind myself that I am the best boss I have ever had and if I want it to stay this way I need to keep moving through the challenges and go forward with confidence in myself.

How do you distinguish yourself from your competitors?

I love this! So many times, I have heard from others why my ideas won’t work or how I am not the only one doing it, and that makes me laugh! There were countless TV hosts before Oprah took over the scene and Blackberry had cornered the market, but it didn’t stop the release of the iPhone.

Determining what your unique value proposition is and own that space unlike anyone else will ensure that you leapfrog your competition.

Heather Monahan on life challenges

Advice and Resources 

What is the best advice you have received recently?

Never give up on your vision. If you don’t believe in your vision whole heartedly, why would anyone else?

What advice would you give to other entrepreneurs?

Follow your dreams especially when others tell you not to. When others show their negativity that means you are onto something different and that in and of itself is absolutely fantastic!

What are your favorite business tools/resources and why?

My network is my favorite resource. After 43 years, I realize that building a solid reputation and a strong network is something that no one can take away from me. Also, that network has stuck by me and created opportunities that I would have never have known how to find.

Leaning into your contacts and asking for help will open doors for you that you may have previously never thought of or known about. Connections are everything in business.

What is a good article or book you have read recently?

My book I just launched in 2018! It is my own story of how I was able to achieve success, but for others I have included all of the tips and turns and tweaks that I am now aware of to ensure that anyone can get ahead quickly and with the least difficulty possible.

My goal is to have put forth a book that shares who I am and how I got to where I am while also making it possible for others to get to exactly where they want to go once they have finished the book.


The Next Steps

What are you currently learning about for your business or looking for help with?

Legal is something I am constantly challenging myself to learn more about. Working for yourself you need to find ways to protect yourself, your brand, and your ideas and that has been a new experience for me.

What are your goals for the next few months and how are you striving to achieve them?

My goals for the next few months are to market my book, to elevate the Rafaella brand through appearances and speaking engagements, and to solidify two other partnerships that I have been diligently working on.

The overarching goal however is to elevate women and ensure that the movement that we are all seeing doesn’t disappear. Instead I want to equip each woman that may not know the role she can play in this movement with specific tasks that she can take on in her own life to ensure advancement for herself and for others.

I truly believe this domino effect will not end if each of us takes steps in our own circles to keep the momentum going. If you are a working mom, stay at home mom, student, or grandmother, there is plenty that each of us can do today to make this world a more fair and just place for everyone tomorrow