Women Of The C-Suite: Monique Hayward of Enactify.ai On The Five Things You Need To Succeed As A Senior Executive

An Interview With Dina Aletras

Be Yourself: As we rise through the corporate ranks or become successful entrepreneurs, it can be overwhelming to feel like you have to always “put on a show.” Instead, just show up as you are. You know when the “clothes don’t fit” because you’re uncomfortable, and others see that, too. Authenticity starts with being true to yourself and what you believe in.

As a part of our interview series called “Women Of The C-Suite”, we had the pleasure of interviewing Monique Hayward.

Monique Hayward is the Co-founder and Chief Marketing Officer at Enactify.ai with over 25 years of experience as a marketing executive, entrepreneur, author, and speaker. She has founded three companies, written two books, and held leadership roles at Microsoft, Intel, and Tektronix. She has a passion for writing, cooking, fitness and travel.

Thank you so much for joining us in this interview series! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

A New York City native who also spent part of my childhood in Columbia, SC, I grew up pursuing my dream of being a journalist. I was the editor of my high school newspaper and idolized the fearless, intrepid reporters who I watched on TV every night and read their articles in magazines and newspapers. By the time I graduated from high school, I decided I wanted to be a political reporter at the Washington Post and enrolled at the University of Maryland College Park, a top-10 journalism school in the Washington, DC area.

At age 18 in 1988, I was not prescient at all about how the internet would disrupt the newspaper industry, but I realized quickly that the best reporters don’t usually start their careers “at the top” at the Washington Post, Chicago Tribune, or New York Times. Rather, you’re expected to pay your dues, work your way up, and not make much money before even getting a chance to compete for those highly coveted jobs at big-city media outlets.

Determined to broaden my horizons and give myself more options, I decided to switch my concentration from newspaper journalism to public relations, which provided the foundation for me to pursue a career in Corporate America. I “sealed that deal” with an MBA in marketing from Case Western Reserve University in 1994 and was on my way to my first job as a marketing communications specialist for Tektronix in Beaverton, Oregon, a company and place I never heard of before a recruiter contacted me about the opportunity. As 1994 was a tough year economically for the country, it was my only offer in hand, and this East Coast girl took a chance on a brand new life in the great Pacific Northwest.

At that point, my career path was clear — i.e., bring my skills and expertise as a deadline-driven, keep-it-simple storyteller and a broad strategic thinker who quickly turns ideas into action to the high-technology industry. That’s led to my thriving, exciting career as a corporate marketing executive, entrepreneur, author, and speaker.

Can you share the most interesting story that happened to you since you began leading your company?

When I began my entrepreneurial journey, well before the #MeToo movement, a male mentor cautioned me to be mindful when pitching to potential investors. He advised that some men may have alternative intentions when meeting with women in business settings, regardless of the professional context. While more women have become angel investors in recent years, the investor landscape is still predominantly male. My mentor suggested that some of the men I’d meet with to talk about investing in my business would fall into three categories:

1. Some men may not have a genuine interest in the business.
2. They admire and respect me as a businesswoman and will be advisors and mentors who will give me advice and access to their networks, but they won’t invest in the business.
3. Some may conflate personal expectations with professional opportunities.

At first, I thought this was ridiculous and laughed it off. I thought potential investors, regardless of their gender, would view me with respect and treat me professionally. It was a stark reality to consider, but it helped me approach these meetings with clarity and confidence.

It has been said that our mistakes can be our greatest teachers. Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

When I was starting out at Tektronix, I was thrilled about my first international business trip to Vancouver, BC. While waiting at the gate, my colleague from our creative agency and I were deep in conversation and completely missed the boarding call! The plane left without us, and though we caught the next flight, I learned the importance of paying attention to the little details — even when you’re excited about the big picture!

Lesson learned? Always keep an eye on the clock, no matter how passionate you are about your work!

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I owe so much of my success to my late maternal grandmother, who set a powerful example of self-discipline and hard work. Living in New York City, she worked the night shift as a nurse at a hospital in Queens and then would battle morning rush-hour traffic to make it in time to open her Harlem beauty salon in Manhattan. She rarely took a day off, and I watched her balance these demanding roles, making sacrifices to build the life she wanted.

Grandma’s relentless work ethic and ability to set and achieve goals were my guideposts, and to this day, I draw inspiration from her resilience and determination to achieve success in both my corporate and entrepreneurial pursuits. Her example taught me that no one succeeds alone, but before asking for help, you must first be willing to do the hard work yourself.

Leadership often entails making difficult decisions or hard choices between two apparently good paths. Can you share a story with us about a hard decision or choice you had to make as a leader?

In late 2019, I launched DRISCOLL Cuisine & Cocktail Concepts, a Phoenix-based personal chef company that I co-founded with Brian Driscoll. We had an amazing ramp with lots of interest from potential clients and a steady stream of inquiries that led to reservations on our books. However, by March 2020, that all came to a screeching halt when the global pandemic led to stay-at-home orders and forced business closures. We had to shut down for almost four months without any path to recovering that revenue because once a client’s birthday passes or a holiday comes and goes, there’s no going back and making that up for most people.

We had a choice to make: 1) Cut the losses as we were not too far along on the path with our new business, or 2) Figure out how to stay in business. We opted for #2, overcoming the struggles by going back to the original plan, revisiting the “why” of being in business in the first place, and staying true to those intentions. And not to mention some pretty savvy marketing and communications from yours truly. 🙂

We also sought the advice and counsel of our closest advisors, who could help us remain rational and strategic rather than emotional and panicky because no one makes good decisions when they’re not thinking clearly. Finally, like with most things in life, you make adjustments and create space for the most important things, and it’s amazing what you can do when you have the right priorities and proper focus on your goals.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. Most of our readers — in fact, most people — think they have a pretty good idea of what a CEO or executive does. But in just a few words can you explain what an executive does that is different from the responsibilities of the other leaders?

For executives, our responsibilities often involve assessing the risk associated with a decision, and the stakes are usually high. Whether it’s an investment in a new product, purchase of a company, collaboration with key industry partners, or any major strategy that ultimately changes the trajectory of the business, executives take significant risks. For me, in some cases, the risk paid off, and in others, the result was a failure from which I learned and grew from the experience.

What are the “myths” that you would like to dispel about being a CEO or executive? Can you explain what you mean?

One of the biggest myths about being an executive is that you’re the ultimate decision-maker, making choices in isolation. In my experience, no executive has made a decision entirely on his or her own.

It’s become cliche for leaders to say that if they’re the smartest person in the room, then they’re in the wrong room, but it’s true. The best leaders place a high value on collaboration, gathering input and perspectives from your team and synthesizing the best insights and data before making a move. I rely heavily on the expertise and perspectives of my team members, peers, and stakeholders in the organization. I view my job as an executive as a guide who empowers and aligns my team’s input to make well-informed decisions that benefit the organization as a whole. Leadership is rarely about dictating; it’s about creating a shared vision and helping others succeed in their roles, so the entire team succeeds.

In your opinion, what are the biggest challenges faced by women executives that aren’t typically faced by their male counterparts?

One of the biggest challenges faced by women executives, particularly women of color, is the lack of advancement opportunities as they ascend to senior leadership. Women often encounter a “glass ceiling,” but for women of color, it’s more like a “concrete ceiling” that’s harder to see through and even more difficult to break. The barrier is a result of structural biases and a lack of sponsorship from influential leaders within the organization.

When I was promoted to my first marketing director role, I was the only Black woman senior marketing leader in a company of 100,000 employees. This came with an immense amount of pressure to continually prove my worth, making further advancement even more challenging. Unlike my white male counterparts, I carried the burden of being a visible, singular example for future generations of women of color — something they never had to consider.

What is the most striking difference between your actual job and how you thought the job would be?

The most striking difference in my role leading marketing at Enactify.ai is how deeply involved I’ve become in discussions that extend far beyond traditional marketing. Initially, I anticipated focusing primarily on thought leadership, brand strategy, and customer outreach, but I’ve found myself at the forefront of significant conversations with our board of directors and advisory board members. My responsibilities also include collaborating closely with our fractional CFO on valuation and market sizing, and I even created the pitch deck for our fundraising efforts. This expanded scope has enriched my understanding of the business and has made my role much more dynamic and impactful than I had anticipated.

Is everyone cut out to be an executive? In your opinion, which specific traits increase the likelihood that a person will be a successful executive and what type of person should avoid aspiring to be an executive? Can you explain what you mean?

Not everyone is cut out to be an executive, and that’s a great thing. People can lead from where they are in the organization and don’t have to be striving to scale the ladder.

If you are self-motivated, confident, driven, and inspirational — and a great storyteller, risk-taker and visionary thinker — then your chances are good that you’ll be a successful executive. On the other hand, if working long hours, always thinking about the business, making sacrifices to lead initiatives or programs, and being at the center of tough decisions don’t appeal to you, then don’t consider executive leadership.

What are your “5 Things You Need To Succeed As A Senior Executive” and why? (Please share a story or example for each.)

1 . Growth Mindset: Approach your life and career with a growth mindset. As Microsoft CEO Satya Nadella has said, be a “learn-it-all” vs. a “know-it-all.”

By my mid-30s, I wasn’t entirely satisfied with my work in marketing and communications and wanted something more fulfilling. As I mentioned earlier, when I was growing up, my late grandmother had a dual career as a nurse and beauty salon owner in New York City. As teenagers, my brother and I would visit her over the summers, and she’d take us to her salon in Harlem, where we’d sit for hours listening to the beauty shop banter and performing chores to help out around the salon. While we were unappreciative and bored most of the time, enough of that experience stuck with me that I was inspired to start my own company alongside my corporate career.

Believing in the power of continuous improvement allowed me to evolve into an entrepreneur. No one told me how hard it would be, but I’ve embraced challenges along the way as learning opportunities rather than roadblocks.

2 . Communication: Learn how to be a good storyteller. I learned early in my career that it’s not enough to let the work “speak for itself.” You need to share your story in a way that’s clear, consistent, and compelling so you’re able to persuade and influence people to take the right action and pursue the desired outcomes.

As a high-tech marketing executive, I’ve made it my mission to simplify engineers’ complexity. I can’t tell you how many times I’ve been in a meeting where I’ve asked, “Can you please explain this in terms my grandma would understand?” Storytelling has allowed me to bridge that communication gap and deliver messages that resonate across all levels of an organization.

3 . Strategic Relationships: No one succeeds alone. Your network is a critical component of your success. Building meaningful relationships; seeking out mentors, sponsors, and role models; and surrounding yourself with smart, ambitious people will elevate your career and give you access to opportunities you might not find on your own.

I’m a strong advocate of assembling your personal board of directors, the handful of trusted advisors and confidants who will push you beyond your comfort zone and challenge you to think differently. Early in my career, I sought out mentors who saw potential in me that I couldn’t see in myself. One executive encouraged me to take on a marketing leadership role in HR at a time when I was focused on building my career in the company’s mainstream business. It was his belief in me that spurred my confidence to make that leap when I thought it would have been a detour that took my career off track. Rather, it was one of best career moves I ever made, and I wound up getting promoted twice in that role. Cultivating relationships with like-minded people who are invested in your success will take you far.

4 . Resilience: The road to the top is not without setbacks; so resilience is an essential part of your career journey. One of the most important qualities of a senior executive is the ability to bounce back from failure and keep moving forward with renewed energy.

My first small business was a restaurant, a notoriously treacherous entrepreneurial road “littered” with many, many failures. I was no different when faced with significant challenges, but it was my determination to keep going — learning from each failure — that eventually led to success. When the restaurant eventually didn’t work out, it was my dear friend and mentor Morgan Freeman who told me that there were lessons in what I experienced and that restaurant wasn’t going to define me or my career in the long term. He was right. I pivoted to other ventures and found new paths to success, including writing my first book.

5 . Be Yourself: As we rise through the corporate ranks or become successful entrepreneurs, it can be overwhelming to feel like you have to always “put on a show.” Instead, just show up as you are. You know when the “clothes don’t fit” because you’re uncomfortable, and others see that, too. Authenticity starts with being true to yourself and what you believe in.

When I first started in leadership, I learned how to differentiate myself among my peers with my positive outlook, high energy, and ability to listen empathetically. Embracing my own voice and perspective gave me confidence, and authenticity helped me build genuine connections. I’m convinced it’s one of the reasons why my teams trust me to lead them.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

I want to turn the 5Cs Framework (Competence, Cachet, Communications, Connections, Coaches) of my book Get Your Hustle On! It’s Not About a Job, But Building a Rewarding Career into an even bigger global movement. What began as casual one-on-one meetings and small-group discussions in conference rooms grew into speeches, media appearances, and a book that’s reached thousands worldwide. I want to do more as it’s been my privilege to help people unlock their potential, guiding them from entry-level roles to senior leadership and entrepreneurship.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

If I could share a private breakfast or lunch with anyone, it would undoubtedly be Scott Galloway, otherwise known as Prof G. As a renowned speaker, author, and entrepreneur, he embodies everything I aspire to be and more. His insights on business, technology, and societal trends resonated with me from the first moment I saw him on “Real Time with Bill Maher” several years ago, and his recent TEDxVancouver talk showcased storytelling at its finest.

I have a long list of questions for Prof G, but my primary focus would be seeking his advice on how to “level up” my career, amplify my influence in the industry, and increase my earning potential. His unique perspective and experience would provide invaluable guidance on navigating the complexities of leadership and impact. Plus, I believe we’d share a lot of laughs, as humor plays a significant role in both our lives, and we don’t take ourselves too seriously. I truly believe that such a conversation could inspire my journey and enhance my ability to mentor others in their careers.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

About the Interviewer: Dina Aletras boasts over 20 years of expertise in the corporate media industry. She possesses an in-depth understanding of growth, strategy, and leadership, having held significant roles at some of the UK’s largest media organizations. At Reach PLC, the UK’s largest tabloid publisher, she served in various director capacities. Additionally, she held leadership roles at The Independent Magazine Group and DMGT. Her extensive knowledge spans editorial, digital, revenue, sales, and advertising.

Upon relocating to Switzerland, Dina took on the responsibility of managing and promoting the international section of Corriere del Ticino — CdT.ch pioneering the English page “onthespot.” She also was the Co-Editor of Southern Switzerland’s first official Italian and English bilingual magazine.