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Heather  Monahan

Heather Monahan

Best-Selling Author, Entrepreneur & Confidence Creator

Heather Monahan

Best-Selling Author, Entrepreneur & Confidence Creator


“Our event jumped to 50 new registrations in one day from posting one of her videos!” -Society of Professional Women, The Maine Line Chamber of Commerce

Confidence is the one thing that will change everything. Heather Monahan’s life and career are proof positive. After 20 years shattering glass ceilings and reaching the C-Suite in media, Heather, a.k.a., “Boss in Heels” has dedicated herself to helping others shift mindsets and develop the transformational confidence that increases sales, achieves goals, invigorates teams and  drives personal, professional and organizational success. Her inspiring, engaging and often, hilarious keynotes go beyond motivating for the moment, event or evening. Audiences leave with tangible takeaways they can put into action immediately.  As one client wrote, “She had our audience laughing, identifying and invigorated.”

Whether you’re facing the glass ceiling, a toxic work environment, or anything in between, Monahan’s 3-Step BAK process in her new book, Overcome Your Villans, will help you evaluate and eliminate any outside or self-defeating blockers between where you are now and where you deserve to be. Heather is also the author of Confidence Creator, the self-published best-seller that took Amazon’s rankings by storm, “trumping” President Trump to capture the #1 spot on their business list.  She also hosts the Creating Confidence Podcast, featuring techniques, strategies and insightful interviews with business thought leaders like Gary Vaynerchuk and Jesse Itzler. Heather also founded and leads Boss in Heels, LLC, a global community dedicated to helping others gain confidence and live their best lives.

All of Heather’s ventures leverage the powerful lessons she learned not only from her meteoric rise from sales rep to CRO, but her unexpected firing by the heir to the family-run business she had spent 14 years elevating to success. After graduating from Clark University in her native Worcester, MA, Heather began her career in sales at the Gallo winery. She quickly advanced to top salesperson and Brand Manager within her first year. For her next job, she took on radio sales and was quickly offered an equity partnership to turn around a fledgling group in the Midwest. Within three years, she more than doubled the station’s value from $27M to a final sale of $55M, earning a reputation as a rainmaker in the broadcasting world. Her success caught the attention of Beasley Broadcasting in Florida where she was hired as Director of Sales and rose to the role of Chief Revenue Officer after numerous promotions. As CRO, Heather oversaw the entire sales organization and took the company from $100 million in annual revenue to over $200 million annually. She also led the group through multiple acquisitions, product additions and a highly successful merger. Before her termination, Heather was recognized as a Glass Ceiling Award winner and as one of the “Most Influential Women in Radio”. In late 2017, Heather chose to make Boss In Heels her full-time job.  A whirlwind followed: Appearances on shows ranging from Headline News, to Steve Harvey, a TEDx talk, and upon the success of Confidence Creator, features in major media including Forbes and USA Today. Her recent speaking engagements include Harvard University, Horizon Media, BNY Mellon, Royal Caribbean, the S.H.E. Summit Bacardi, the WNBA, University of Miami Business School and many others.

Known for working with clients to customize her highly motivational keynotes, Heather is the energizing choice for sales kickoffs, women’s groups or any organization looking to kickstart performance and drive results.  Leading audiences through her own journey, Heather challenges audiences to start on their own path—developing the confidence they need to become the best, most innovative and authentic version of themselves.

Speaker Videos

Speaking Reel

TEDx: Me Too’s Mis-Step or Me Too’s Mistake

On Overcoming Fears

Confidence Creator Promo

Find Your Superpower

On Steve Harvey Show

Speech Topics

Becoming a Confident Woman

How to create confidence and become the woman you have the potential to be!

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 will create it for yourself.

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. The current culture we live in applauds when men win awards and shares the news yet a woman would feel petrified to share the news of her accomplishment. 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 apologies and putting ourselves on equal footing with others 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 relate with your audience and empower them to create change that will 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 to have the tools, understanding and inspiration to make the changes needed. Confidence isn’t given, it is created.

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.

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 is 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.

The Confident Leader

How to create confidence and become your most powerful self!

What would it be like if talented employees flocked to you and you had zero turnover on your team? You would achieve your goals, get promoted and feel fantastic! If you have not been able to figure out what it is that’s holding you back from becoming the best leader on your team then it is time for something new.

Whether we know it or not there are underlying challenges in each company that can present hold backs keeping our leaders from growing and taking risks. When there is a lack of growth and risk taking there is a lack of innovation and lack of creativity. Employees want to be a part of a team and company that is in growth mode, creating and innovating daily. People want to work for people that they can relate to and who can help them grow. While traditional leadership training is valuable and relevant to hold employees accountable and implement training programs, it takes more to really get to the next level.

Creating teams of people where Confidence is nurtured and developed not only improves employees productivity it improves their lives. Taking the first step to fine tune your confidence creation plan and strategy will allow you to step into your most authentic self. The more authentic, relatable and real you are the more your people will come to you and run through walls for you. Becoming your most confident self allows you to become vulnerable which happens to be a unique and highly sought after trait amongst leaders. Allowing for vulnerability on the team allows for a safe place for employees to ask for help and ask questions they may otherwise be afraid to share.

Heather Monahan has 20 years of experience leading, training, and mentoring thousands of employees and hundreds of leaders to reach their potential and in turn teach their teams how to do the same. In this enlightening session Heather will share with you the key steps that need to be taken, the work that must be done and the plan to leave with in order to implement it in your office and your life. Creating confidence for you is imperative but to become a true leader you must learn to create confidence in others and foster it throughout your community.

The Confident Sales Team

How to create your confidence and become your most successful self!

So often as sales professionals there is a trainer that will walk you through the simple steps that you need to take to create your goals, identify the right prospects, sell your benefits and go for the close. Sales professionals are looking for something more, something different, something that delivers results and drives revenue. Sales professionals want to separate themselves from the sea of mediocrity that is out there. That begins with providing a solution for their challenges.

So many sales people don’t call on the clients that they really want to go after out of fear of rejection. Sales people become discouraged when one seller keeps winning and they begin to give up on themselves and even start looking for other jobs. Sales people are afraid to ask questions because they don’t want to appear as if they don’t already have the answer. Sales people don’t ask for help because they are afraid of what the response may be. Sales people’s biggest hold back is lack of confidence and that is the single differentiator between the top sales person and everyone else on the team.

In every exchange someone is sold. Whether it is you being sold to pick up your friends 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.

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.