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Chief Change Officer
#356 Mary Shea: From Oboe Solos to Sales Strategy—A Career Reinvented — Part One
00:22:34
From orchestras in Mexico to revenue teams in tech, Mary Shea rewrote her career with a PhD, a sales quota, and zero regrets. In Part One, she shares how she bridged the worlds of art, business, and leadership—proving reinvention is a mindset, not a moment.
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- [00:13]
Vince Chen
Hi everyone. Welcome to our show. Chief Change Officer, I'm Vince Chen, your ambitious human host. Our show 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 shay, the co CEO of MediaFly, a leading revenue enablement 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 troubled. Imagine going from a classical musician with a PhD to an entry level sales job, from playing music to 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 being paralyzed by the weight of her background as a well educated musician, a mantle 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 is a powerful reminder of the resilience it takes to truly embrace change and chase success on one's own terms. When I come to know Mary before I even met her in person, a common friend, so to speak, is her partner, Waverley 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 eight 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 is a good fit for me and me to fly. Which I already assume it is. You bet Mary. Here we go.
- [03:46]
Mary Shay
Thank you for having me. I'm thrilled to reconnect with you. It's been quite some time, hasn't it?
- [03:51]
Vince Chen
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 MediaFly. Start with something brief and then we'll dive into specific details. Sure.
- [04:29]
Mary Shay
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 growth 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 a number 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 in 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, you know, 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. And 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.
- [07:15]
Vince Chen
At Forrester, you were the analyst. You analyze things, you analyze people, you analyze businesses.
- [07:23]
Mary Shay
There's really two sides of my Forrester career. I was at Forrester 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 Forrester 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 in demand. And I worked for a number of folks who are very, very well versed in the world of B2B sales. And they were very generous and 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 forster analyst. But I did start to be fair at an entry level sales position and work my way up the chain there.
- [09:34]
Vince Chen
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?
- [09:47]
Mary Shay
There are a couple of different themes or threads that were big motivators for me. When you think about sales, sales is the 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 it 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 even. 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 and 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 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. Pence 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 want to 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.
- [12:06]
Vince Chen
Yep, enabler. I really like this work. 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 will 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 enablement leadership. That is Very empowering.
- [12:37]
Mary Shay
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 chief 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 years. 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 a 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 acquired are in very key positions here at MediaFi. 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.
- [14:28]
Unknown
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- [15:00]
Vince Chen
I like that term mini CEO. You and Carson, the official co CEO of Mediaflight, you got a lot of mini CEOs on their own, in their own space. They all have their own potential to grow. If I can summarize this way, Yes.
- [15:20]
Mary Shay
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 a great breadth and depth of experience and expertise in those.
- [15:34]
Vince Chen
Areas other than sales, business, and tech. I know you are 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.
- [15:54]
Mary Shay
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. 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 breadlines 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 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.
- [17:46]
Vince Chen
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.
- [17:58]
Mary Shay
Well, that's one of my favorite topics. I'm so glad you asked. So leaderfly 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 this, 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 the 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 solutions. 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's 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 activity 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 a 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 have the last interactions been? When was last time we talked to them? How are they consuming the content that we send? And that allows me at any given time to understand what is the health of the deal, the health of the pipeline and my forecast so that I can course correct or provide the right coaching as needed.
- [21:17]
Vince Chen
So you got a whole suite of tech enabled solutions blended with human services?
- [21:25]
Mary Shay
Yes.
- [21:28]
Vince Chen
So how does the AI technology impact your space especially in the context of human and machine interaction?
- [21:39]
Mary Shay
Yeah, I'll give you my perspective on a couple of different Personas. Right.
- [21:46]
Vince Chen
Next time Mary is going to break down how AI technology is not just a password but 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 co CEO Governance model. Ever wonder how having two captains steering 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, subscribe to our show. Leave us top rated reviews. Check out our website and follow me on social media. I'm this Chen, your ambitious human host. Until next time.
- [22:59]
Mary Shay
Take care.
- [23:09]
Unknown
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