Chief Change Officer
#356 Mary Shea: From Oboe Solos to Sales Strategy—A Career Reinvented — Part One
Sat, 10 May 2025
Mary Shea didn’t follow a traditional path. She composed her own.In Part One of this three-part series, Mary walks us through the bold decisions that took her from professional oboist to PhD to sales analyst—and eventually to co-CEO of Mediafly. Along the way, she’s picked up more than titles: she’s developed a philosophy that blends intellectual rigor, creative play, and social equity.She opens up about what it’s like to enter the business world a decade “behind” her peers, the financial freedom sales can offer underrepresented leaders, and how she’s helping build not just tech products—but leadership pipelines that reflect the real world. This episode is for anyone thinking of switching lanes, catching up, or starting over.Key Highlights of Our Interview:From Mexico to Management: Her Unlikely Start“I played oboe in symphonies, earned a PhD in musicology—and then started over in sales.”Sales as a Social Equalizer“If you’re good at it, you can rewrite your life. It gave me the power to fund causes, uplift others, and lead on my own terms.”Behind, But Not for Long“I came into business 10 years behind my peers. That lit a fire—I moved fast, and I moved with purpose.”Creating the Playbook, Not Just Following It“I need intellectual stimulation. Managing is fine, but building strategy? That’s what lights me up.”Enabling Others Is the New Power Move“My role now is to empower my team like mini-CEOs. Their wins are my metric.”Scaling With a Human Lens“We acquired five companies in under two years—not to show off, but to build something smarter, faster, and more inclusive.”Pushing for True Diversity in Sales“Only one-third of B2B sellers are women. That has to change—and I’m using my platform to help drive it.”Mediafly’s Mission: More Than Sales Enablement“From revenue intelligence to buyer engagement, we’re building the full tech stack—without losing sight of people.”_________________________Connect with us:Host: Vince Chan | Guest: Mary Shea PhD --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.EdTech Leadership Awards 2025 Finalist.18 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 1.5% Podcast.Top 10 US Business.Top 1 US Careers.>>>170,000+ are outgrowing. Act Today.<<<
Chapter 1: Who is Mary Shea and what is her unique career path?
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 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. I'd come to know Mary before I even met her in person. A 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 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 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 Mediaflot.
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Chapter 2: How did Mary transition from music to business?
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 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 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, 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 an oral tradition. It was a wonderful experience. As I came to the end of my Ph.D. time, I felt like the palette was a little bit too small for what I saw in my professional career path. 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 start 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.
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Chapter 3: What role did Forrester play in Mary's career transformation?
You analyze people.
You analyze businesses.
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 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 industry.
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 poster analyst. But I did start, to be fair, at an entry-level sales position and worked 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?
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Chapter 4: How does Mary view sales as a tool for social change?
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 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 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, 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. 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.
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Chapter 5: What are the key motivations in Mary's career journey?
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 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.
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 months. Our competitive set and 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 are acquired are in very key positions here at Mediafly. So I see my role and 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 have courage. 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 since. 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 Mediafly, 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, 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 a great breadth and depth of experience and expertise in those 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.
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