Chief Change Officer - #187 Mary Shea PhD: From Classical Music to Closing Deals—The Art of Reinventing Your Career – Part One

Episode Date: February 19, 2025

Mary Shea’s career is proof that you don’t have to stick to one soundtrack. From a classical musician to a leading voice in sales leadership, she’s taken some bold risks—and in this first episode of a three-part series, she’s sharing the lessons she learned along the way. As General Manager of Hire Quotient and former co-CEO of Mediafly, Mary is on a mission to amplify underrepresented voices and reshape sales leadership. With insights from her time at Forrester, she also dives into the digital transformation of sales and how creativity plays a bigger role in business than you might think. Key Highlights of Our Interview: From Music to Business “I started as a classical musician, playing with the Mexico City Philharmonic and Guadalajara Symphony. But when the career palette felt too small, I took a leap into business, changing my life forever.” Sales: The Great Equalizer “Sales is one of the few fields where hard work and skill can lead to financial independence, regardless of where you start. That independence allows you to make meaningful changes in your life and others’.” Playing Catch-Up with Purpose “Coming into the business world with a PhD put me 10 years behind my peers, but it also ignited a fire. I moved quickly, knowing every opportunity was critical to closing that gap.” Creating the Playbook “I’m not just about managing to a playbook—I love creating it. The intellectual stimulation of building strategies with teams and seeing them succeed is what drives me.” _________________________ Connect with us: Host: Vince Chan | Guest: Mary Shea PhD --Chief Change Officer-- Change Ambitiously. Outgrow Yourself. Open a World of Deep Human Intelligence for Growth Progressives, Visionary Underdogs, Transformation Gurus & Bold Hearts. 6 Million+ All-Time Downloads. Reaching 80+ Countries Daily. Global Top 3% Podcast. Top 10 US Business. Top 1 US Careers. >>>100,000+ subscribers are outgrowing. Act Today.<<<

Hi, everyone. Welcome to our show, Chief Change Officer. I'm Vince Chen, your ambitious human host. I'll show it is a modernist humility for change progressives in organizational and human transformation from around the world. In this episode, I'm thrilled to welcome Mary Shea, the co-CEO of MediaFly, a leading

revenue and ableman company that raised $80 million in capital to turbocharge its growth. Mary's story is downright inspiring. Mary, a proud LGBT community member and women's empowerment advocate, has taken a path less truffled. Imagine going from a classical musician with a PhD to an entry-level sales job, from playing music to playing a key role in sales, then rising to become a CEO after working as a forester analyst. If I had to capture Mary's journey in just two words,

it would be beyond boundaries. We are our worst enemies, scared of failure or what others might think. But in Mary's case, instead of failure or what others might think. But in Mary's case, instead of being paralyzed by the weight of her background as a well-educated musician, a mentor that could have been seen as baggage in her new arena, she chose to reinvent herself. This wasn't about giving up. It was about moving forward, unburdened. It's a powerful reminder of the resilience it takes to truly embrace change and chase success on one's own terms. But I come to know Mary before I even met her in person.

Our common friend, so to speak, is her partner, Waverly Deutsch, who was my former professor of entrepreneurship at Chicago Booth. After I heard all the wonderful things about Mary's business success in the sales space, I finally got to sit down with her over dinner when both of them came to Hong Kong before Covid. Other than good food and wine, fun conversation, I was impressed by all the changes she has led, building herself up with so much resilience and intelligence. As I was putting together the guest list for the podcast, I thought of her right away. I emailed her directly.

Within 8 minutes, I got her reply. There, she said, I would love to be on your podcast. Please send over details. Our team will take a look to make sure it's a good fit for me and MediaFly, which I already assume it is. You bet, Mary. Here we go. Thank you for having me. I'm thrilled to reconnect with you.

It's been quite some time, hasn't it? Yes, a couple of years, a lot of changes. This podcast is about change. You are the perfect person to talk about that. Now, let's start with your own change. I don't mean just a resume type of introduction, but more about milestones that you've experienced back in your school days studying music

and then move through the business landscape. And now you are the co-CEO at MediaFlight. Start with something brief and then we'll dive into specific details. Sure, happy to share that with your listeners and with your audience. I do love change and if you think about me,

I've been in the business world and walking the world for a while here now. I'm also a Gemini, which means I constantly like being challenged, I'm intellectually curious. I sometimes am impatient and like to take on new things. So my professional journey is wrought with lots of risk and lots of change. And I'll share with you that the biggest risks I've taken

have resulted in the biggest upsides, whether it's professional personal growths or economics or typical roles that you might think about. I started out my career as a classical musician. I was an oboist. So for those of you who don't know, oboe is a double reed instrument like bassoon, and it's one of the most difficult orchestral instruments there are. I started playing the oboe when I was 12. My whole life was really geared to being a professional classical musician. I played in nombre of youth orchestras. I went to college and earned degrees in music performance. And then I went to Mexico and played in the Mexico City Philharmonic and the

Guadalajara Symphony Orchestra. I really lived my dream when I was in my very, very early 20s, which is wonderful because I didn't have to have a midlife crisis then. So I got to do what I wanted from day one. And I came back to the States after making a name for myself in Mexico and thought, well, if I want to support myself as a working musician, classical musician, I should get a PhD so I can teach and have some stability in my income and I did that.

I got a PhD in musicology, which is the study of Western art music or music that's written down. And also the degree was in ethnomusicology, which is Musics of the World or more likely music that's passed down in oral tradition. It was a wonderful experience. As I came to the end of my PhD time, I felt like the palette was a little bit too small for what I saw in my professional career, how I saw my professional career taking shape.

Serendipitously, I met some people from Forrester who recruited me to come join the company and started in sales there. And I took a big, big leap of faith and that was probably the single most transformational moment in my professional and personal life. It changed the trajectory of my life, both from my spouse to the business role to the economics that I was able to make, and to the impact I was able to have on things that I'm passionate about, Vince.

One of the big passions is really leading, inspiring, and motivating global teams. At Forrester, you were the analyst. You analyze things. You analyze people. You analyze businesses. There's really two sides of my Forester career. I was at Forester for a decade and I was what George Colony, who's the CEO and founder there, calls a boomerang.

So I started out my sales career at Forester in the mid to late 90s as an SDR. So one of those folks that actually is front of the cycle rep that sets meetings, that drives interest and demand. And I worked for a number of folks who were very, very well versed in the world of B2B sales and they were very generous. I learned a lot from them. Forrester was on a trajectory at that time where I got promoted almost every six to 12 months. It actually kind of spoiled me because that's not really the way of the world when you think of it. But I had a great run there.

I was there for about five years in a range of different individual contributor roles in sales, sales management, and also sales leadership. I ended up opening up the first satellite office for Forrester in Chicago. Then I left for a range of different reasons to go out and make a name for myself globally and take on a role as a general manager and chief revenue officer, which was my dream. But subsequently I went back to Forrester around 2015. I was on the product side and what I did as an analyst was really looked at the changing buying and selling dynamics in the business world.

So things were changing rapidly with the digitization of the sales process, sales, digital transformation. I looked at the emergent sales tech landscape. And then a passion of mine also is really diversity, equity, inclusion. What does it take to get more females into the sales role? Because I see high-level sales as one of the key paths to the C-suite and specifically the CEO. And I personally have a passion for seeing more and more women, folks who identify women

in CEO positions at Fortune 100 companies. And I think sales is one of the best directions to get there. So that was really my platform as a porster analyst. But I did start, to be fair, at an entry-level sales position to work my way up the chain there. Now that you look back, if you analyze your career life, do you see any common threads or themes or factors or drivers of motivation? What would that be? of themes or factors or drivers of motivation. What would that be? There are a couple of different themes or threads

that were big motivators for me. When you think about sales, sales is a great equalizer because if you're really, really good at it, you work really hard at it, you can make a lot of money. And so making money wasn't a primary focus for me in sort of my career decisions. It was my passion and what I loved in life. But once I started making a lot of money

because of my sales success, I realized that I had the power to really change things, to do wonderful things for my family, to be generous with extended networks of friends, to funnel my money into charities that align with my values as a person. And I don't even want to go down this path because we're so politically fractured here in this country right now, but even funnel money to political candidates.

And I'm quite involved in national politics here as a fundraiser. Once I got a sense of the impact that I could have by having financial independence, that was a big motivator for me and also remember I got a PhD. So I started very late my professional business career. If I wasn't moving really quickly and taking advantage of every opportunity, If I was moving really quickly and taking advantage of every opportunity, that I was going to fall behind because I was about probably 10 years behind my peers in terms of my earning potential because I had taken an academic path, which I wouldn't change for the world. But when I came out to the business world and saw what was possible,

my hair was on fire in a good way and I really wanted to move. And so I moved quickly. The other thing that is really important to me is that I just need the intellectual stimulation. I can't just manage to the playbook. Hence, part of me is that I have to create the playbook, work with teams and what those right plays are and then roll it out. The creative process is really important to me in the business world.

The other theme is I just love working with people. I'm competitive. I like to see people who I work with, who may work for me at this point, be super successful. I wanna be an enabler for those folks. So those are some of the common themes that I think you could find against any role that I've had over the last 20 years.

Yep, enabler. I really like this word. Some of the best leaders I've worked with and for over years, they really try to enable my success, even before I believe in it. They would say, just do it. I have confidence in you. I'll help you with that. I'll make you a success.

That's what I call an Aberman leadership. That is very empowering. Yeah, it's really empowering. We're at a wonderful position here at MediaFly where we've recently gotten a very substantial round of funding that allowed me to go out and hire some folks who had actually been very, very successful in terms of scale ups. We have a new Chiefs Customer Officer and she's absolutely phenomenal.

We also have wonderful leaders at MediaFly who have joined us through acquisition. We acquired five companies in the last 20 months. Our competitive set, peers and analog companies were hunkering down and retrenching and trying to make every last dollar of their venture capital last so that they didn't lose unicorn status and take it down round. We've been able to be highly, highly innovative. A number of those leaders that have come in as CEOs from companies that are acquired are in very key positions here at MediaFly. innovative. A number of those leaders that have come in as CEOs from companies that are acquired

are in very key positions here at MediaFly. So I see my role in the role of Carson, our founder, is to really step back, enable, empower those folks, support them, allow them to do their jobs. We need to remove obstacles. We need to encourage. We need to build confidence if someone's a little bit reticent, and we need to instill in all of our C-suite, our executive leadership team, that they are the kind of mini CEOs of their own functional area of the business. We all need to be aligned. They should be running that piece of the business and coming to Carson and me for advice, guidance, to poke holes in their strategy and to get help when they've reached roadblocks or impasses. That's really how I see my role.

I feel pretty confident in what I've accomplished, Vince. To see others be successful is almost more motivating to me than my own personal trajectory. When everyone else is successful, you're successful as a CEO. I like that term, mini CEO. You and Carson, the official co-CEO of MediaFlight, you got a lot of mini CEOs on the road in their own space. They all have their own potential to grow if I can summarize this way. Yes, I think that's right. The other thing is that they have very deep and expansive subject matter

expertise, whether that's in product, whether that's in customer, they bring very great breadth and depth of experience and expertise in those areas. Other than sales, business, and tech, I know you're a passionate champion in driving diversity issues forward, especially with respect to women and LGBT communities. Tell us a bit more about your work there. Yeah, it's a topic that's near and dear to my heart. And yeah, I am a proud member of the LGBTQIA

community. And I think it's important to put myself out there because there's lots of people who are struggling. In terms of women, specifically, right now, the research that I've done shows that about a third of sellers in B2B sales are women. And obviously, we're at least 50% of the population. So I'd love to see selling organizations be more representative of the world around them. Not just talking about white women. So how do I and how do others empower folks who are black or brown skin? Like, how do we get more diversity writ large across the organization and the selling organization? That's something that I really want to do more of.

So what do I do? I certainly amplify the voices of diverse voices across the board whenever I can. If I have speaking engagements that I can't do, I try to pass them on to others. I am encouraging. I'm a coach and mentor. I do as much as I can to help folks who are generally part of underrepresented groups be really successful in sales. And this goes back to I didn't grow up with a silver spoon. My dad actually was a child of the

Depression. His family lost all of their money and he had to stand in bread lines to get food for our family, his family, because his parents were too embarrassed to do so. If anyone has a parent who's gone through that Great Depression or any other economic challenges globally or worldwide, you never lose that. I came from a modest background and I worked really, really hard. And I think sales is a great equalizer where people can get social equity and economic equity very quickly if they can be successful.

And I want to help folks do that. Now, let's dip dive into MediaFly. I really want to learn more about your work there. What sort of problems you're trying to solve and whose problem? Who are your clients? Sure, well, that's one of my favorite topics. And I'm so glad you asked.

So Meteorfly is a revenue enablement company. And when I say revenue enablement, I'm talking more than just direct sales. When you think about enablement, back in the day when I was at Forrester, we called it sales enablement. And what sales enablement meant was, how do you get the right content into sellers at the right moment in time so they can deliver that in a cohesive way to their buyers.

Today, we talk about revenue enablement more broadly because we're not enabling just the direct selling force. There's a whole range of routes to market that companies use. And it could be ecosystem partners, it could be marketplaces, it could be e-commerce on their website, and of course, their direct selling organization. So enablement has morphed really away from or expanded away from just sort of thinking about enabling the direct selling organization to how do you enable everyone who touches a customer and also even enable the buyer? That's just a little bit of a background so that people understand kind of the difference

in why we call it revenue enablement. What revenue enablement does essentially is help everyone in the go-to-market organization engage with prospects and customers in efficient and effective manner. So that could be everything from our solution serving up dynamic interactive content that can be delivered in a workspace or in a digital sales room, providing rich signals back to the seller and the selling organization on how that content is being consumed. It can be leading with a quantitative discussion around how their products and services are going to change their end customers'

ability to be more successful from a revenue and business perspective. So we have a value tool that helps sellers use this interactive tool to navigate a value-oriented discussion on what the potential impact of product and service could be. We also have intelligence, so call recording, call coaching, analytics around how those calls are going between buyers and sellers, and then revenue intelligence, which actually grabs and automates all the buyer-seller interactions that happen over the course of a cycle, captures those into our system.

And then we have bilateral sync with the CRM, broader CDP, if companies use that or prefer that. And we provide this rich data set that it shows you the buyer and seller activities that it's been having over the course of the time, which provides tremendous insights that companies can use with the algorithms to be smarter about how they interact and engage as a revenue leader. Or even as CEO, I can go onto our system and get an energy score of every prospect that we're talking to. Where they are in the pipeline is that energy score red, yellow, orange.

And what are the last interactions been? When was the last time we talked to them? How are they consuming the content that we sent? And that allows me at any given time to understand what is the health of the deal, the health of the pipeline in my forecast so that I can course correct or provide the right coaching as needed.

So you got a whole suite of tech-enabled solutions blended with human services. Yes. So how does the AI technology impact your space, especially in the context of human and machine interaction. Yeah, I'll give you my perspective on a couple of different personas, right? Next time, Mary is going to break down how AI technology is not just a buzzword, but a game changer for sales teams and their revenue goals. Plus, we are tackling a topic that is a bit out of the ordinary,

the cold CEO governance model. Ever wonder how having two captains during the ship compares to the solo CEO journey? How do they make it work? And what's the secret to balancing the benefits and the risks of sharing the leadership? Thank you so much for joining us today. If you like what you heard, don't forget to subscribe to our show, leave us top-rated

reviews, check out our website, and follow me on social media. I'm Vince Chen, your ambitious human host. Until next time, take care. I'm Vince Chen, your ambitious human host. Until next time, take care.