Chief Change Officer
#357 Mary Shea: From Oboe Solos to Sales Strategy—A Career Reinvented — Part Two
Sat, 10 May 2025
Is two better than one?In Part Two of this series, Mary Shea—former co-CEO of Mediafly and former General Manager at Hire Quotient—shares how she navigated one of the most unconventional leadership models in business: co-CEOship. From building trust with her co-leader to balancing responsibilities across time zones and product lines, Mary unpacks the human side of shared power—and why mutual respect beats ego every time.She also explores how AI is transforming sales effectiveness, not just efficiency, and why today’s revenue teams need to look more like collaborative ecosystems than traditional hierarchies. Plus: what every leader can learn from marriage, tennis, and the occasional business referee.Key Highlights of Our Interview:AI for Sales: More Than Speed, It’s Strategy“We’re not replacing reps—we’re freeing them up for high-impact work. That’s the real ROI of AI.”The Death of the 80/20 Rule?“With smarter tools, smaller teams can do more. We’re heading toward 80% of sellers driving 100% of revenue.”AI as a Coach, Not a Crutch“Think of AI as a coach on your shoulder. Helpful, but never a substitute for personalization or judgment.”Behind the Scenes of Co-CEO Life“It works because we trust each other. We split duties, share a vision, and treat decisions like a dialogue—not a turf war.”The Marriage Metaphor (Yes, It Fits)“Being a co-CEO is like a professional marriage. You need communication, shared values—and sometimes an executive coach.”Slower Decisions, Stronger Outcomes“We may debate more than solo CEOs. But those debates lead to smarter, more resilient choices.”When the Umpire Steps In“If we hit an impasse, we turn to our board and investors. Every partnership needs a higher court.”Scaling Without Silos“We empower leaders as mini-CEOs—but only if we keep the org aligned. Otherwise, remote work just breeds islands.”The Bigger Game: Building Equity Through Leadership“AI, revenue, strategy—it all comes back to who gets to lead. And how we help more people rise.”_________________________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 are the hosts and guests of this podcast?
Hi, everyone. Welcome to our show, Chief Change Officer. I'm Vince Chen, your ambitious human host. Our show is a modernist community for change progressives in organizational and human transformation from around the world.
Last time, we heard a very inspiring and interesting story about Mary, transforming from a classical musician with PhD to entry-level frontline salesperson, and now the co-CEO of a rising revenue enablement company. In this episode, 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 co-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? Let's find out.
Chapter 2: What is Mediafly and how does it support revenue enablement?
Mediafly is a revenue enablement company. 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's being consumed it can be leading with a quantitative discussion around how their products and services are going to change their end customers
We also have intelligence, so call recording, call coaching, analytics around how those calls are going between buyers and sellers. And we provide this rich data set that it shows you the buyer and seller activity that's been happening over the course of the time, which provides tremendous insights that companies can use with the algorithms.
Chapter 3: How is AI transforming sales teams and their effectiveness?
So how does the AI technology impact your space, especially in the context of human and machine interaction?
Chapter 4: What are practical examples of AI augmenting sales and marketing work?
Yeah, I'll give you my perspective on a couple of different personas, right? That might be our customers. So if I'm a sales rep, how am I going to use AI?
First of all, we've got to embed it into our system so that we know if a sales rep's talking to a certain company of a certain size and a certain industry and a certain role within that company, based on where they are in the sales cycle, the system will automatically surface up content that makes sense to be shared at that point. So how wonderful is that?
We're giving automatic recommendations on, hey, you should share this based on who you're talking to, based on what we've seen work with this type of customer. That's one really quick example. Certainly with generative AI, if you're in sales and you're not using it to spin up emails.
let me be really careful here like you have ai is just simply augmentation it's not going to replace sales people it's not going to replace the work that sales people do so if you're spinning up a renewal note for example you've got to customize 40 to 30% of that AI. If I get an email to me, Mary, I hope this email finds you in good health and good spirits.
I just like click delete onto the next one. I know that's exactly generated by bot and I'm not going to waste my time on it, but it could be a huge savings if you can get the guts of that email and provide the appropriate amount of customization so you can work much faster and you can save your time for higher value activities, right?
Negotiating deals, closing deals, expanding stakeholder involvement. If I'm a RebOps leader, I might want to use AI to completely understand where am I at risk in my renewals over the next three quarters. By at risk, I might want to look at in a visualization, are we single threaded?
And by single threaded, that means like we're just talking to one person at this company who's a customer, or are we talking to five people? And if we're talking to five people, are they people at director level or BP level above? And so AI can be used and our chief product officer has done this for me where I can take a quick visualization and be like, okay, we need to work on this account.
We need to add more executive stakeholders. We need to do a quarterly business review with this. I need to be involved in this. And it gives you a quick snapshot of where your risk is, Vince, so you can de-risk it before you lose the renewal. And then certainly I think we all know the marketing use case, which is I'm not great at staring at white space when I write research and blogs.
And if I can kind of put in the appropriate prompts that I get sort of the structure and initial page of a blog, I'm going to customize 70% of that. I'm going to use maybe what the AI gave me from a structural standpoint, and then I'm actually going to use it once I'm finished and customize it.
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Chapter 5: How does AI balance efficiency and personalization in sales?
And if you were to come up with a metaphor that captures AI's role in the sales space, what would that be?
Chapter 6: What is the future of sales teams with AI and the evolving 80/20 rule?
When people think of sales tech or rev tech, as we're calling it now, people immediately go to efficiency. But I think the golden mean is really about the effectiveness, which is how can I really customize and personalize my messaging to my customers and prospects so that it drives some sort of urgency or outcome? Everybody wants that personalization piece. I think that we can get it through AI.
So I'm super, super excited. I do think it will lead to smaller, more agile sales teams. Eventually it'll lead to a movement away from the 80-20 rule, which is, in case your listeners don't know, 80% of your revenue is generated by 20% of your salespeople. That's been the rule of thumb for like 100 years or 50 years or 20 years or whatever it is.
And now I think we'll have smaller, more agile sales teams that are augmented with technology and you'll start to see 100% of the revenue delivered by 80% of your sales team. We're not quite there yet, but that's the vision that I had when I wrote about this at Forrester. There was a seminal report called
The B2B consultant seller Rainz, and on Rain, that's sort of a double entendre with Rainmaker, but also the words I used was R-E-I-G-N, Rain. So this is their kingdom. This is their moment. With regard to AI, I called it as sort of the coach that was going to sit on the shoulder with that salesperson, helping them be much more advisory oriented to really deliver that impact to their customers.
I think we're very, very close to seeing that vision I had become a reality. The biggest thing I want to leave your audience with is it is not a replacement. It's simply augmentation and don't shortcut on the customization.
Now, Mario, with the necessary capital secured, a talented team in place, and the promise of advanced technology, there is another critical element in the success equation of any business, which is leadership. You're navigating this journey with Carson as co-CEO, a setup that's somewhat unconventional in tech and large enterprises, though not unheard of.
Could you share what went through your mind when you decided to begin this co-leadership path? And more importantly, how has the experience been for you so far?
Yeah, I think you need to think long and hard about it. It's not a trivial model and it's probably not for everybody. And it's not for every company at every stage of its growth journey. There's a moment in time where it can really work well. And there are some criteria that you need to think about before you might want to consider taking it on.
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Chapter 7: What is the concept and challenges of the co-CEO leadership model?
I will say that the model is becoming more and more popular. There's a couple of things I'd love to direct your listeners to. Number one, there's a recent Harvard Business Review article that's called, Is it time to consider too? And that was published, I think, at the end of 20, around 2022 or 2023. And Carson and I looked at this article. We found it when we were talking about it.
He had extended the offer for me to join. And it was a very, very gracious offer. But honestly, I was a little taken aback, Vince, because you don't always see the right outcomes. And I think Benioff had just let go his most recent co-CEO. And I was a little bit skeptical initially.
But what the thesis of the article is, the premise of the article is that today's world, before you even get internal to running your company, has become far more complex than it's ever been before. Whether that's maturation of a range of different technologies, namely generative AI, which is moving at the speed of sound right now.
Whether it's political instability that we're seeing in a range of different places. across the globe, whether it's the backlog of the supply chain that's not really working after COVID, whether it's going through a global pandemic, whether it's a social justice movement world.
Chapter 8: What criteria make co-CEO models successful according to Mary Shea?
I haven't even gotten to challenges in the Middle East and Russia and Ukraine, which obviously impact financial markets and everything. It's a complicated world. And so the premise of this article was, you know, there's no one individual that can handle everything. Why not consider having two folks?
The other piece of it is it doesn't make sense to hire two CEOs if they have the exact same skill set. It's really important to have two people who have a shared vision. but a complimentary skill set. That was really key. I'd encourage your listeners who might be interested in learning more about this model to number one, take a look at the HBR article.
And then our friends at Freakonomics published a podcast on this around Christmas time, where they did extensive research on this model, kind of brought together folks that are behind the model and others that were really against it. It's a really super interesting dialogue. The biggest thing for Carson and me is that we've known each other for a decade.
Mediafly and Carson were my customer when I was a Forrester analyst, so I worked with them a lot over the many, many years. When I went back into industry, when I moved on from my analyst role, I took an evangelist role at Outreach, which is a Seattle-based unicorn that folks may know about. And Carson invited me onto the board. So I've had a bird's eye view of the company.
Working with Carson, we have immense deep trust for each other. He's focused on the product. We divide and conquer with him, looking at product, financial, people, investor relations. I focus on making the market, educating the market, doing things like I'm doing today, helping folks understand the difference between sales enablement, revenue enablement. I oversee all of our customer facing teams.
Carson oversees the product, but we have the same vision for the product and the future of the company. And so it works. but it's not for everybody. Certainly there are times when decision-making is slower and I'm sure Carson would say this if he were here, there's some days where he just kind of wants to do it the way he wants to.
I want to do things the way I want to and we can't because we have to really come to alignment between the two of us. We can be in two places at the same time. We can close big deals as two co-CEOs to really make Some of our customers feel like, wow, the level of white glove treatment they have with two CEOs is pretty amazing. We can really drive the business forward in a range of different ways.
And there's a lot of really positives that are about it. But it's not for the faint of heart. And I'm sure Karsha would agree with me when I say that.
Sharing leadership is nothing new. It reminds me of my days in the financial markets, where co-head arrangements in investment banks and financial houses were standard. I had a chance to work directly under two co-CEOs leading a global business. Their setup worked well. They shared responsibility and authority. They complemented each other with their skill sets, styles, and approaches.
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