293 - Unlocking the Power of Storytelling and Listening in Marketing and Business with Enactify.ai's Monique Hayward
13 Feb 2025 · 25 min
In this episode of Listening with Leaders, host Doug Noll interviews Monique Hayward, CMO and co‑founder of Enactify.ai. Monique shares her unconventional career journey—from a childhood ambition to be a Washington Post reporter, through a journalism degree, public‑relations work, an MBA, and senior roles at Tektronix, Intel (22 years across multiple functions) and Microsoft—to founding a startup that re‑imagines PDFs. Enactify’s technology embeds interactive, e‑commerce‑enabled experiences directly into static PDF documents, turning traditional catalogs into seamless shopping tools; the first proof‑of‑concept is a holiday gift guide for an Oregon winery. Monique explains the market gap: despite AI and digital transformation, PDFs remain a stale medium, yet the U.S. catalog market is a $50‑60 billion opportunity. She outlines Enactify’s storytelling‑centric marketing approach, emphasizing the need to serve audiences, maintain relationships, and meet customers where they are rather than racing ahead. The conversation also delves into the importance of listening—both in personal and business contexts—highlighting Monique’s experience using therapy to improve communication with her personal‑chef business partner. Finally, she reveals a unique mentorship with Morgan Freeman, forged during a celebrity spokesperson project at Intel, illustrating the long‑term value of authentic relationships. Throughout, the dialogue underscores how storytelling, empathetic listening, and strategic timing converge to drive startup success.
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Welcome to Listening with Leaders. I'm Doug Noll, lawyer turned peacemaker. I teach executive leaders how to listen to emotions rather than words so that they can become the leaders everyone wants to follow. And I teach those same leaders how to be authentically present, available, and connected to their families despite being insanely busy. I have learned that we are 98% emotional and only 2% rational. Learning how to listen to emotions is, in my experience, the foundational skill of life. Stick around to the end of the show and I'll reveal how you can be on our next guest in 15 to 20 minutes. So let's get started.
Monique Hayward, welcome to Listening with Leaders. You are a founder and the chief marketing officer of a company called Enactify. Which can be found at enactify.ai. Interactive PDFs.
Yes. Who would have thought?
Welcome to the show. Let's start off just with a quick backstory. Tell us a little bit about your business, your educational background and business, your business experience, that sort of thing.
Yeah. No, absolutely. I'm happy to share and thank you very much for the invitation to be here. I'm super excited about this conversation. Let me tell you a little bit about where I am and, and who I am. So I'm in Portland, Oregon. So Beaverton, actually, the suburb of Portland. And I've been living here for 30 years now, and it's really hard to believe because when I started out on my career journey, I was an East Coast kind of girl. And so I split my childhood between New York City and Columbia, South Carolina. And I grew up thinking that I was going to be a journalist and very specifically a journalist who was a reporter at the Washington Post and working on the political desk. That was— I was that clear when I was like even in the 5th grade that I really wanted to do that. And so everything that I did up to that point was in the direction of being a journalist until I got to journalism school. And then, not that I was prescient, Doug, at all about what would happen with the newspaper industry, how the internet would change the world or any of that. I just knew I wanted to make more money than what journalists were going to make because nobody starts out at a big city newspaper like the Washington Post or the New York Times. Or the Boston Globe, you start out at the state newspaper in Columbia, South Carolina, writing obits. And I'm like, no, not me. So I stayed in the J-school, but I shifted my focus to public relations. And then that actually provided the foundation for me to get a marketing degree. So an MBA that I got from Case Western Reserve University in Cleveland, Ohio. And I took my first job after grad school at a company called Tektronix. And, and they're in the test and measurement business. So a high-tech company here in Beaverton, Oregon. And back then I said Oregon because again, being an East Coast kind of girl. And I took this job and then did that for 3 years. And then I went to Intel and I worked at Intel for 22 years. And the way that I like to describe my career at Intel, Doug, is that I moved around to move up. And so I worked in every organization within Intel with the exception of sales, finance, and manufacturing, every other organization I worked in. And then, from there, I went to Microsoft. And, and so I worked at Microsoft for a few years. And then now, as you described in the opening, I am the chief marketing officer for Startup, a company that is focused on bringing interactive digital experiences to static documents and creating amazing storytelling and e-commerce capabilities that will take your business to the next level.
So I gotta ask, what is it like moving from two of the— Intel's having its problems now, but still, it's—
Yeah.
One of the— two of the largest, most influential technology companies. 22 years at one company.
Yeah.
And then, and becoming a founder of a startup. That, that, for a lot of people, that's a dream. But I also gotta think that's a culture shock.
Yes, it is. And I'm glad that you set me up for The other path that I developed with my career. So in addition to my corporate career, I also have an entrepreneurial career. And so I've started my own businesses. Uh, I have been a restaurant owner. I was a partner in a software company, and my current small business venture is a personal chef service with a short-term vacation rental property down in Phoenix, Arizona.
And yeah, so I've had quite that, that gives you a good excuse to get out of the wet and go down to Phoenix in the winter.
Yeah.
No, it's a business expense. How can that go bad?
I wonder. Definitely. So I've had that, that, that startup, that entrepreneurial spirit alongside my corporate career for many years. And, and yes, it's shocking in a way to go from this massive scale of an Intel or Microsoft. All the way down to the 3 of us who are the co-founders of Enactify. And then thinking about my, my small business hat that I put on, my partner and I who are running this personal chef and short-term vacation rental property that we're hustling and scrambling, just trying to keep, keep ourselves visible and ensuring that we deliver a fantastic experience for our clients who stay at our place or who book our personal chef service.
Wow. Yeah. So talk to me a little bit about Enactify. What was the need in the market that you saw that got the three of you to put this thing together?
Yeah, the story of Enactify is really interesting. It's a little bit of the stereotypical, a student at Stanford had an idea and decided to start a company. Who would have thought? And so our founder, the original technology founder, is a gentleman named Ahmed El Gamal. And he is a student at Stanford, PhD student at Stanford. And I'm sure that a lot of your listeners and you as well, having been on the entrepreneurial journey as well, will understand how a lot of business ideas are born out of personal pain. And that's the story here where Ahmed was in his PhD program at Stanford and wanted to collaborate with other PhD students at universities around the world on different research projects, different papers, etc. And they did did not have a great way to collaborate in doing that. And so he had an idea to put together a software platform that would allow for real-time communication and collaboration among the PhD students who were in his, in his network working on the same research problems. And, but he was smart enough to realize that college students don't generally have a lot of money. Let's try to figure out some business use cases where this technology could actually deliver some value. And so he decided to engage with an engineering firm, put together some prototype software capabilities, and then move down the path of hiring a professional team. And so that's where the three of us who are the executive team came on. And, and then we actually started just iterating more on the possibilities and thinking about what people need, especially marketing people. That's our target audience, people who are creating content, people who are trying to increase engagement with their customers and, and drive more revenue for their business. And that's the need that we were trying to, trying to address in the market is that when you think about what's happening with digital transformation, you think about what's happening with AI, you think about all of these things that have been revolutionizing the way that we work, the way that we play, the way that we interact with each other. The one thing that has been left behind is the lowly PDF, right?
So I use PDFs every day, right?
Exactly. You hit— yeah, you hit export to PDF like pretty much all the time. And usually what happens is that once you've exported that document, you don't think about it anymore. And so what we're doing is saying, no, you've got a treasure trove of content that you can reuse, repurpose, recycle in a new and interesting and engaging way to really deliver more value to the business. And so that's what we're unlocking for.
I'm trying to figure out how this works. So what I— if, if I send you a— if I have a PDF document that I want to create, make it engaging, more reader engaging, is this stuff all embedded into the PDF document itself? So it's a standalone?
That is correct, my dear. I will tell you about—
so you got to have— so obviously you have to have— it has to be linked to the web. In order to pull information, not putting all the data into the PDF itself.
Exactly. Exactly. So I'll tell you about an interesting use case that we have collaborated with, actually an Oregon winery. They are going to be launching their holiday gift guides here pretty soon. And, and our technology is featured as a core part of their online gift guides. And, and what we have done is that we have created e-commerce capability within the static document of this gift guide. And so if you wanted to buy, say, the Chardonnay that they're offering or the Pinot Noir that they're offering, and you're in their, in their catalog, then you don't have to bounce to their website. Because a lot of times what happens when you get catalogs, you'll do your browsing and then you'll do your shopping, if you will. You might take notes, you might make annotations and that kind of thing, but you can't actually shop until you go to their website.
Right.
And a lot of things break in between there. And so what we've done is that we said, hey, you know what, we can create a seamless shopping experience right within the document so that you never have to leave that document until your shopping cart is full and that you are ready to check out and go onto the website and put in your credit card.
The winery then sends the PDF catalog out to all of its customers saying, here's our Christmas catalog. All you gotta do is open it up and go for it.
That's right. And it's going to work for them.
Huh? How's it working for them if they send it out?
Fingers crossed. We're launching as we speak.
Okay.
And that's exactly what we need. We need to get that data and we need to be able to demonstrate for— because we're still in startup space, right? This is our very first customer, our very first proof of concept. And we are hoping that all goes so that we can use that for the next set of customers that we can go and pitch for enactify.ai.
It strikes me that this could be big.
It could be huge.
It could be.
It's gonna be big. It's gonna be big.
You think about how big e-commerce is now.
Yes, absolutely.
And how many companies—
and how many companies—
yeah, I was gonna say how many customers rely on their websites with WooCommerce or Shopify or any of the other big platforms.
We estimate that catalogs alone, just retail catalogs alone, are a $50-60 billion business in the United States. Huge. Yeah. So it's huge. Definitely. If we could just get even a little sliver of that. Exactly.
Don't need to get greedy here. Just a little small piece.
No, we're, yeah, we're not trying to, we're not going for world domination of e-commerce platforms. We're just trying to get our little space.
You're the chief marketing officer. I guess that means you're the voice of the company trying to get people to pay attention. How, what have What are the processes you're using for doing that?
Yeah, a couple of things. So I've spent my career, whether it's been in big companies or in my own ventures, as I described, being a megaphone marketer. And so I really think about opportunities to build awareness, to create positive perception, increase engagement, and tell fantastic stories about what it is that we are delivering to solve a real customer's problem. And, and I wanna lean in a little bit on the storytelling piece because I think that as leaders and, and as successful professionals who have, you know, acquired so many skills and have so much experience and a lot of expertise that they bring to the party, a lot of times we just don't have the time or the effort, the energy that we take to tell great stories about what it is that we're doing. And, and so being, being someone who actually has a journalistic mindset, I think about how to tell a good story a lot because that is what really resonates with people. So I think the foundation of what I do from a marketing standpoint is what is the story that we're trying to tell? How does it really connect with the audience that we are trying to serve. And I say serve very specifically, right? The audience is not there to just listen to what you have to say. You— the audience is there for you to engage and to serve. You show up in service to your audience. You don't show up to just give them information or feed them a whole bunch of marketing mumbo jumbo. And then I think the final thing is that we really want to ensure that we maintain engagement and build relationships. Oftentimes in high technology, we are so guilty of getting on to the next so fast, right? Because the world is changing really fast. Lots of innovation. The industry is known for breakthrough capabilities in one form, shape, or another. But a lot of times we get too far ahead of our customers and where they are, and we're still like not finished with this one thing before we're on to the next. And so the one of the things that I'm really an advocate of in terms of the customer journey is meeting the customer where he or she is and staying there and ensuring that we build that relationship so that they're ready to go on to the next when the next big thing is coming. And a lot of times we just abandon customers on the back end of the journey and be like, oh, you know what, sorry, we're done with that. We're on to the next.
I think part of that, I think that part of that is there's a certain boredom. Yes. Get this adrenaline rush of getting this product going and get the product that works. It's going, it's getting accepted by the market. Now you're bored. Now what do I do? I don't want to just spend my life maintaining this product. I want to go on to the next big thing. What's the next big exciting thing? Adrenaline rush I can get.
Yes.
And people forget the importance of paying attention to the people they're serving.
Absolutely. And I think also to that point, there's a lot of money to be made in investing in each part of the journey, right? To make sure that your customers are going to remain loyal, that your customers are being served, that they are spreading the word about you in a positive way. I think, again, you're at the mercy of the relationships that you have built or destroyed along the way. That is true, I think, in business, that's true in your personal relationships as well. You are only as good as the relationships that you have built or destroyed.
Oh, I love that. That's exactly right. And that's what I do. I teach people how to build strong relationships by listening.
Yes.
So I'm curious, Monique, what do you think is unique about you that you bring to the table that's allowed you and your partners to get Enactify off the ground and looking towards what could be significant success?
I think that there are a couple of unique things. One was that I think we've got, like I said, a really interesting founder story, a really interesting origin story that people can relate to. The second thing is that we're the right company for the right moment. Like I said, AI is hot, digital transformation is hot, and, and it's, there, there's an opportunity here for technologies that are emerging to create a new customer experience to have their moment in the sun as well. And so I think we have an opportunity here to ride those coattails of the, the really big investments that companies are making in their platforms around AI and other digital innovation.
And what is it that you bring to the table that's unique?
Me?
What do I bring specifically?
Yeah, poor little old you.
Poor little old me. I bring, I think, a wealth of knowledge and expertise around, like I said before, the storytelling piece. I have traversed a career that has incorporated both a corporate element as well as an entrepreneurial element. And so I'm comfortable with being on either side of those, either side of those tracks, so to speak. What I've learned from corporate America, I've brought into my small businesses and vice versa. There's a lot of times what happens when I think people get into a situation where they're working for a startup company and they've come from a big company, they don't know how to scale it down because we're used to working with multibillion— multimillion-dollar budgets and multibillion dollars in revenue, or having teams of 30, 40, 50 people, 100 people. When it's just you and 2 or 3 other people, you really have to scale that down, right? And then you really have to understand where you show up is, you know, how the company is going to be successful. When I was at Microsoft, I could take a day off and the stock price would do whatever it was going to do.
Right?
Not, you know, nothing stopped because Monique Hayward took a day off. But, you know, with this venture as well as my own personal ventures, if I don't show up, then something just does not happen.
Right. And that's, and that's absolutely true. So I wanna pivot a little bit. This call, show is called Listening with Leaders because I believe that listening is the foundational skill of life, and there aren't a lot of good listeners out there. You have obviously spent a lot of time learning how to listen. Tell us about your journey. Of learning to be a good listener.
Yes. In fact, I'm a speaker as well as an entrepreneur, and I've written a couple of books. And I've also done just a few other interesting things in my career. And oftentimes when I'm up on stage and having delivered a presentation and do the Q&A, how you do afterwards, people often ask me, what would you have done earlier in your career that you wish you had done that you could see now. So what would you tell your 20-something-year-old self? And I always say, I wish I would have shut up more and listened better, right? Because I think a lot of times, especially when we're younger, we're trying to make our mark. We're trying to prove to the world that we've got value, we've got worth, we've got significance, we have point of view, we have all of that. And sometimes the better option is just to sit back, listen, observe, hear what's going on, and then contribute. Right. I wish I had done more of that earlier in my career because then when I did learn, it served me well.
Right. It's so interesting. What's so interesting is children were ordered to listen.
Yes.
In school, we're ordered to listen. When we're a subordinate, we're ordered to listen. But we're never taught how to listen.
Yeah, really.
There's that active listening crap that doesn't work, that is still— I can't believe it's still being taught, you know, it's so horrible. But we're really not taught how to focus and listen to another person to make sure that they feel heard. And we don't under— and we're never really taught the value of validating somebody else, especially their feelings. We may completely disagree with what they're saying, but if they're having an emotional experience, they're angry, for example, we can calm them down by simply telling them that they're angry, reflecting their emotions. And we're not taught this stuff. And I, I keep thinking about what a different world it would be if we all had the ability to listen to each other at a deep and profound level.
Yeah, you're absolutely right. And this has equal applicability whether you're in your personal relationships or in your business relationships. That's right.
Even more, I would say.
Yeah, definitely. I will tell you a story about my personal chef business. My business partner is a gentleman named Brian Driscoll, and we created this company 5 years ago. And in the first couple of years of the company, we were having some serious challenges from a communication standpoint. And I decided that we would go get a therapist.
Okay.
Right. It's like, because see, a lot of times people don't think, like, wait a second, this is my business relationship and I'm gonna need, oh no, we need some help here because our business depends on relationship, us being able to communicate. And I tell you, Doug, our therapist exactly talks about how we need to be empathetic listeners.
And that means— that's right— and that means learning how to listen to and reflect each other's emotions.
That's right, absolutely. And be direct, because I think a lot of times what happens, people fall into this passive-aggressive—
that's right— because they're, they're trying to manage their own anxiety. Around the other person's upset.
Yeah.
They want to be heard. They don't know how to listen. They don't know how to meet the other person's need to be listened, and the other person doesn't know how to meet their need to be heard. And that's where conflict comes from.
Yeah, absolutely. And I tell you, it was one of the best investments that we made as business owners, recognizing that this was an issue that was getting in the way of our success. Excellent. And I encourage those of your listeners who are in partnerships, business partnerships, who have founder relationships that are challenged or have—
Yeah, come to me. This is what I do. I teach you how.
Yeah, exactly. This is what you do. Yeah.
Yeah.
Get the help. Recognize that you need help and that don't let those issues fester. Don't let that conflict overtake the whole reason why you're in business in the first place.
And as I tell my clients, do what I tell you to do, you'll never have a fight or argument again in your life.
Yeah.
It's that, it's that powerful.
Good.
One more, one more question, Monique, and I'll let you go. Tell us one thing that's unique about yourself that we wouldn't know about unless you revealed it to us.
I happen to have a fantastic mentor and sponsor in my life who everybody knows and always asks me, oh my God, what's the man like? And that is Morgan Freeman.
Is that right?
Yes.
How did you meet him?
Yeah, so I did a project with him when I was working at Intel many years ago, and I hired him as a celebrity spokesperson, and he did an event for me in Atlanta, and I wound up being his handler for the day.
Wow.
Yeah, and so we got to know each other, and it turns out that he owned a restaurant business at around the same time I had my restaurant business. And he was also going to be filming his next movie at the time in Portland.
Oh, wow.
So yeah, so he came to Portland and he called me and he came to my restaurant and oh, it was just an amazing experience. And ever since then we have been mentor-mentee relationship and he's so sage and so amazing. And yes, the voice. Oh my gosh. You hear that voice on the phone. Oh my gosh. Yeah, it's crazy.
He strikes me as being a really authentic, kind, wise man.
He is. He's all of that and then some. And, and I'm all the wiser for having invested the time and effort and energy to build that relationship over the last, oh my gosh, 14, 15 years now. Wow.
Good for you. That is unique. Monique, it's been great chatting with you. Thank you so much for all of your insights and your time this afternoon. Shukran. My audience will love you, I'm sure.
Oh, good. Thank you so much, Doug. I appreciate the invitation. Doug Noll here.
Thank you so much for listening to Listening with Leaders. If you are a successful executive leader who would like to be on this program, please visit podcast.dougnull.com/podcast. If you got something out of this interview, would you please share this episode on social media? Just do a quick screenshot with your phone and text it to a friend or post it on the socials. If you know someone that would be a great guest, tag them on the social media to let them know about the show and include the hashtag #ListeningWithLeaders. I love seeing your posts and guest suggestions. We are regularly putting out new episodes and content. To make sure you don't miss any episodes, go ahead and subscribe. Your thumbs up ratings and reviews Your reviews go a long way to help promote the show and mean a lot to me and my team. Want to know more?
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