Chief Change Officer
#188 Mary Shea PhD: From Classical Music to Closing Deals—The Art of Reinventing Your Career – Part Two
Wed, 19 Feb 2025
Who needs a solo act when you can have a dynamic duo? In Part Two of this series, Mary Shea, General Manager of Hire Quotient and former co-CEO of Mediafly, takes us inside the world of co-CEOship—a growing leadership trend that’s part genius, part juggling act. Mary unpacks what makes it work: trust, complementary skills, and a shared vision. But she’s also refreshingly candid about the pitfalls—slower decision-making, the need for a strong board, and why even the best co-leaders need a “business couples counselor.” If you’re rethinking leadership structures, this one’s for you. Key Highlights of Our Interview: AI’s Impact on Sales Teams “AI is paving the way for smaller, more agile sales teams, moving away from the traditional 80/20 rule toward a future where 80% of the team delivers 100% of the revenue.” The Rise of the Consultant Seller “AI acts as a coach on the salesperson’s shoulder, helping them become more advisory-oriented, and enabling deeper impact in customer interactions.” Why Two CEOs? “In today’s complex world, no single leader can address everything, from geopolitical challenges to the rapid pace of AI innovation. The co-CEO model allows for a divide-and-conquer approach.” Challenges of Co-Leadership “Decision-making can be slower, and sometimes we wish we could just do things our way. But alignment is key, and when it works, it’s incredibly impactful.” Who’s the Umpire? “Our ‘umpire’ is our investor and board. If we truly can’t resolve a disagreement, we rely on their input as the ultimate decision-maker.” The Professional Marriage “Co-CEOship is like a professional marriage—it requires resilience, commitment, and sometimes even a ‘marriage counselor’ in the form of an executive coach to navigate tough patches.” _________________________ 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.<<< --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.12 Million+ All-Time Downloads.Reaching 80+ Countries Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>140,000+ are outgrowing. Act Today.<<<
Chapter 1: What is the main topic of this episode?
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: How does AI technology transform sales teams?
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.
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? 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?
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Chapter 3: What are the benefits and challenges of the co-CEO model?
Chapter 4: How does AI help balance efficiency and effectiveness in sales?
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.
to get rid of word redundancy, to make sure the language I'm using is as succinct as possible, to make sure that I am presenting this in the most easily digestible format that's obviously in my voice. Those are a couple of quick ways. We could iterate on this for quite some time because there's many, many use cases. It's super exciting.
Like I said, there are lots and lots of use cases. We don't have time to cover them all. Let's take a step up, look at the impact of AI in a broader sense. I'm really interested in your perspective on balancing efficiency with effectiveness. So how do you envision AI transforming this balance? And regarding the old 80-20 rule, how do you see AI modernizing these concepts perhaps?
And if you were to come up with a metaphor that captures AI's role in the sales space, what would that be?
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
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Chapter 5: Why is the co-CEO model becoming more popular?
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.
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.
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