Heather Monahan, 43
Founder of Boss In Heels (and in recovery from corporate America)
Heather Monahan is a boss in every sense of the word. After spending the bulk of her career climbing the corporate ladder, the rockstar executive and single mother decided to abandon the proverbial hamster wheel and instead dedicate her life to helping women squash self doubt. Her initiative, rightfully dubbed #bossinheels, aims to destroy the male-oriented vision of what being a “boss” means. “Become your number one cheerleader instead of your biggest saboteur,” advises the blonde beauty. “It will change your life.”
1. What made you choose this career path? What has been your greatest achievement?
My entire life has led me to where I am today. Having struggled with my own insecurities early on and not having a strong female mentor led me to the decision to empower others and give them the insight I was always searching for. While working in corporate America and doing what I thought I was supposed to do, I stumbled upon what I was meant to do. It didn’t happen overnight it was more of an evolution over time. As I grew more confident in myself it became overwhelmingly clear what I needed to do; I needed to be the person that I needed when I was younger, I needed to shine my light so others could see. My greatest achievement is risking my comfort zone to be the person I am becoming and showing my son through my actions not just my words that everyone should live up to their potential and chase their dreams.
2. What’s the biggest criticism/stereotype/judgement you’ve faced in your career?
You can't dress feminine and be taken seriously.
3. How did you #SWAAYthenarrative? What was the reaction by those who told you you “couldn’t” do it?
My own self-doubt. To overcome self-doubt you must take action and develop your confidence muscle. Who you surround yourself with is everything – fire negative people in your life and watch you take off. How you see yourself is how others will see you – speak kindly to yourself, make yourself a priority, love yourself the same way you would a baby – this takes practice but it can become a habit.
Journal to see how far you have come and keep track of all of your small wins. Turn scarcity into abundance by writing down three things a day that you can be grateful for. Moving into your fear and realizing that you are okay will give you strength for your next challenge while backing away does the opposite. Speak up in meetings, speak up for yourself and speak your truth. Becoming your number one cheerleader instead of your biggest saboteur will change your life. Go for it!
4. What did you learn through your personal journey?
Early in my career I was taken aside by a very stoic and cold woman who told me that I dressed inappropriately for work and needed to wear pantsuits and more formal conservative attire. I have never been a very conservative pantsuit type of girl so this conversation didn’t go well.
Time and time again in my career I have been told to look a certain way or dress a certain way and with much difficulty, I did not listen. I was sexually harassed at my first job and was told that the way that I dressed invited these types of challenges.
Years later I remember being at a company meeting and sitting in on a roast where I was tagged the “VP of Cleavage” apparently this was a knock at the strapless dress I was wearing. I excused myself and cried in the bathroom for a few minutes before composing myself and returning to the meeting. The ironic thing is in the past year as I have launched my personal brand to empower others, I have heard so much positive feedback and appreciation for my sense of style. Believing in yourself and being yourself will always pay dividends in the end but isn’t always easy along the way. Be true to you.
5. What’s your number one piece of advice to women discouraged by preconceived notions and society’s limitations?
The only limitations that can be put on you are the ones that you put on yourself. Make a conscious choice to challenge the status quo. I learned that Oprah was fired from TV many years ago, only to become the media maven that she is today. Everyone will be told ‘no’ and why they are wrong or not good enough, and those are the moments you pivot and find a way to make it work in spite of the negativity. If success was easy everyone would have it. Let nothing stop you in chasing your dreams and nothing will.
Sweaty Palms & Weak Responses
Early spring 2018, I walked into the building of a startup accelerator program I had been accepted into. Armed with only confidence and a genius idea, I was eager to start level one. I had no idea of what to expect, but I knew I needed help. Somehow with life's journey of twists and turns, this former successful event planner was now about to blindly walk into the tech industry and tackle on a problem that too many women entrepreneurs had faced.
I sat directly across from the program founders, smiling ear to ear as I explained the then concept for HerHeadquarters. Underneath the table, I rubbed my sweaty palms on my pants, the anxiousness and excitement was getting the best of me. I rambled on and on about the future collaborating app for women entrepreneurs and all the features it would have. They finally stopped me, asking the one question I had never been asked before, "how do you know your target audience even wants this product?".
Taken back by the question, I responded, "I just know". The question was powerful, but my response was weak. While passionate and eager, I was unprepared and naively ready to commit to building a platform when I had no idea if anyone wanted it. They assigned me with the task of validating the need for the platform first. The months to follow were eye-opening and frustrating, but planted seeds for the knowledge that would later build the foundation for HerHeadquarters. I spent months researching and validating through hundreds of surveys, interviews, and focus groups.
I was dedicated to knowing and understanding the needs and challenges of my audience. I knew early on that having a national collaborating app for women entrepreneurs would mean that I'd need to get feedback from women all across the country. I repeatedly put myself on the line by reaching out to strangers, asking them to speak with me. While many took the time to complete a survey and participate in a phone interview, there were some who ignored me, some asked what was in it for them, and a few suggested that I was wasting my time in general. They didn't need another "just for women" platform just because it was trending.
I hadn't expected pushback, specifically from the women I genuinely wanted to serve. I became irritated. Just because HerHeadquarters didn't resonate with them, doesn't mean that another woman wouldn't find value in the platform and love it. I felt frustrated that the very women I was trying to support were the ones telling me to quit. I struggled with not taking things personally.
I hadn't expected pushback, specifically from the women I genuinely wanted to serve.
The Validation, The Neglect, The Data, and The Irony
The more women I talked to, the more the need for my product was validated. The majority of women entrepreneurs in the industries I was targeting did collaborate. An even higher number of women experienced several obstacles in securing those collaborations and yes, they wanted easier access to high quality brand partnerships.
I didn't just want to launch an app. I wanted to change the image of women who collaborated and adjust the narrative of these women. I was excited to introduce a new technology product that would change the way women secured valuable, rewarding products. I couldn't believe that despite that rising number of women-owned businesses launching, there was no tool catered to them allowing them to grow their business even faster. This demographic had been neglected for too long.
I hadn't just validated the need for the future platform, but I gained valuable data that could be used as leverage. Ironically, armed with confidence, a genius idea, and data to support the need for the platform, I felt stuck. The next steps were to begin designing a prototype, I lacked the skillsets to do it myself and the funding to hire someone else to do it.
I Desperately Need You and Your services, but I'm Broke
I found myself having to put myself out there again, allowing myself to be vulnerable and ask for help. I eventually stumbled across Bianca, a talented UX/UI designer. After coming across her profile online and reaching out, we agreed to meet for a happy hour. The question I had been asked months prior by the founders of my accelerator program came up again, "how do you know your target audience even wants this product?".
It was like déjà vu, the sweaty palms under the table reemerged and the ear to ear smile as I talked about HerHeadquarters, only this time, I had data. I proudly showed Bianca my research: the list of women from across the country I talked to that supported that not only was this platform solving a problem they had, but it's a product that they'd use and pay for.
I remember my confidence dropping as my transparency came into the conversation. How do you tell someone "I desperately need you and your services, but I'm broke?". I told her that I was stuck, that I needed to move forward with design, but that I didn't have the money to make it happen. Bianca respected my honesty, loved the vision of HerHeadquarters, but mostly importantly the data sold her. She believed in me, she believed in the product, and knew that it would attract investors.
From Paper to Digital
We reached a payment agreed where Bianca would be paid in full once HerHeadquarters received its first investment deal. The next few months were an all-time high for me. Seeing an idea that once floated around in my head make its way to paper, then transform into a digital prototype is was one of the highlights of this journey. Shortly after, we began user testing, making further adjustments based off of feedback.
The further along HerHeadquarters became, the more traction we made. Women entrepreneurs across the U.S. were signing up for early access to the app, we were catching investor's attention, and securing brand partnerships all before we had a launched product. The closer we got to launching, the scarier it was. People who only had a surface value introduction to HerHeadquarters put us in the same category of other platforms or brands catering to women, even if we were completely unrelated, they just heard "for women". I felt consistent pressure, most of which was self-applied, but I still felt it.
I became obsessed with all things HerHeadquarters. My biggest fear was launching and disappointing my users. With a national target audience, a nonexistent marketing budget, and many misconceptions regarding collaborating, I didn't know how to introduce this new brand in a way that distinctly made it clear who were targeting and who we were different from.
I second guessed myself all the time.
A 'Submit' button has never in life been more intimidating. In May 2019, HerHeadquarters was submitted to the Apple and Google play stores and released to women entrepreneurs in select U.S. cities. We've consistently grown our user base and seen amazing collaborations take place. I've grow and learned valuable lessons about myself personally and as a leader. This experience has taught me to trust my journey, trust my hard work, and always let honesty and integrity lead me. I had to give myself permission to make mistakes and not beat myself up about it.
I learned that a hundred "no's" is better than one "yes" from an unfit partner. The most valuable thing that I've learned is keeping my users first. Their feedback, their challenges, and suggestions are valuable and set the pace for the future of HerHeadquarters, as a product and a company. I consider it an honor to serve and cater to one of the most neglected markets in the industry.