Chief Change Officer - Mediafly co-CEO Mary Shea PhD: Pioneering a Dual CEO Blueprint

Episode Date: March 11, 2024

We’re back with the much-anticipated sequel in our series, where Mary delves deep into the transformative powers of AI in revolutionizing sales tech and boosting revenue like never before. Prepare for a deep dive into her top 5 predictions that are set to redefine the industry! But wait, there’s more! Ever wondered about the dynamics of sharing the helm? Mary opens up about her groundbreaking journey as a Co-CEO at Mediafly, offering a rare glimpse into the challenges and triumphs of dual leadership. And, for a twist you didn’t see coming, Mary shares a book that has profoundly impacted her worldview on humanity. It’s a revelation that’s bound to intrigue and inspire. Gear up for an episode packed with insight, innovation, and intrigue. Your next big idea might just be a play button away! Connect with Us: Host: Vince Chan | Guest: Mary Shea Chief Change Officer: Make Change Ambitiously. A Modernist Community for Growth Progressives World's Number One Career Podcast Top 1: US, CA, MX, IE, HU, AT, CH, FI Top 10: GB, FR, SE, DE, TR, IT, ES Top 10: IN, JP, SG, AU  1.3 Million+ Streams 50+ Countries

Hi everyone, welcome to our show. 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.

Leaderfly 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 an 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 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 is 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 salespeople. It's not going to replace the work that salespeople 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 could save your time for higher value activities, right?

Negotiating deals, closing deals, expanding stakeholder involvement. If I'm a RevOps 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, what are we single threaded? And by single-threaded, that means 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 VP 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 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 all 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 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, you know, 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 reigns. And on reign, that's sort of a double

entendre with rainmaker, but also the words I used was R-E-I-G-N, reign. 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, Mary, 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 are 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. 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 two CEOs? 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. 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 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 complementary 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 you 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. What tied everything

together was their mutual trust and having an empire, a boss about them to make the final calls. But when external market forces have changed, internal office environment has shifted, and their personal circumstances have diverted. Partnership did not sustain. That's no different from my own journey as a co-founder in New Ventures. Initially, we shared trust and viewpoints and respected each other's independence, leaning on interdependence

when necessary. But as circumstances began to emerge, when one party's behavior becomes unfriendly or, I should say, counter-relationship, it often triggers a similar response from the other side. The whole dynamics of a relationship or partnership changed. Here, the psychology concept, reciprocity, plays a crucial role in the dynamics and the final outcome. How do you guys resolve conflict as and when it happens? Yeah, I mean, I think the first thing is that, you know, we're really honest with each other and we have those conversations and we have the trust that we're going to get to a place where we can resolve it in a way that works. So I would say when we're at an impasse, and there haven't been major impasses, but they happen from time to time, we'll both take a step back. We will educate ourselves more, we'll learn more and we'll come back. Sometimes we'll come back to the table one, two, three, four times.

Eventually we get to a place that we both can live with. So like I said, there are times when the decision making takes longer, but we both feel like we've kind of gotten to a better decision. I'm a fan of tennis. So I'm thinking of if you've got two star players, like co-CEOs, who's your part? At some point, something happened. At the same time, it's kind of like a marriage and you know, any loving couples, they may at some point go to a consultant or something. In- Yeah.

In- Space. Who's the other part? Who's the referee? Oh, yeah. Yeah. Well, let me say I love tennis too. And, you know, we do have an umpire and that umpire is our investor and the board. So at the end of the day, we have a wonderful investor in VIP Ventures, which is out of Atlanta. If we get to a point where we can't resolve things together, we've got a boss. Everybody has a boss.

And our boss is the board and our investor. And so we can certainly go in that direction if need be. But I will pull the thread on another sort of line of thinking here, which is this is a professional marriage. I've been married for or I've been with my spouse for close to 30 years now. As you know, as people know who have made that type of commitment, there are good years and sometimes there's not so good years. You have to have the resiliency to be in it for the long term. Sometimes you have to go to a marriage counselor and sort it out.

I think having an executive coach for both of you, whether that's sort of an internal coach or someone you hire externally, can be really, really helpful because it's a highly complex model. And having someone who can get you through those tough patches, I think can be really helpful. At the end of the day, we do have an umpire and that's called the board. I like to think of it as a tennis match when two leaders of equal caliber face off, akin to players matched in skill. But I'll be the first to admit,

real-life leadership dynamics are far more complex and full of ambiguities than a straightforward tennis match. Perhaps based on my own time in the thick of these leadership dynamics, let me share a few insights. First off, think of tennis as the ultimate showdown where players fight for their glory, fame, rankings, and of course, the prize money, is the essence of competition. A zero-sum game where one's win is an other's loss. But when we talk about shared leadership, the dynamics shift. It's not about winning or losing against each other. It's about playing a positive-sum game.

Here, the strategy is coopetition, blending collaboration with competition. Not just claim a larger slice of the pie, but to make the pie bigger for everyone involved, both for the individuals and the business. Now, let's talk umpires. In tennis, the umpire's decision is immediate and final, helped by technology with clear rules and transparent procedures. Everything happens live with instant feedback on questionable actions. And then, the game moves on.

Business, however, doesn't have the luxury of an on-the-spot empire. Even with governance structures, shareholding frameworks, and policies in place, those in oversight capacities, such as directors and investors, cannot always see, witness, and judge events as they unfold. This delay introduces different risks, such as gaps in time, reality, expectations, and information, making the business landscape much more complex than any sports arena.

Let's talk about the whole people dynamics and structure thing. A concept foreign to the tennis court, where the only crowd management needed is ensuring the audience stays quiet. However, in a world of business, voices and noises are ever-present. Mary's got this cool idea about making everyone a mini-CEO, which sounds super empowering, but then that's the possibility of everyone doing their own thing, creating little islands or silos within the company. With the adoption of remote work, these people dynamics and political undercurrents

present challenges that are harder to identify and address because of lack of physical presence and direct observation. As a business skills, these dynamics multiply. Here's a thought. What if we bring in some specific roles to help balance things out? Like executive coaches as independent advisors for co-CEOs to keep them grounded. Or a chief of staff to connect the dots between different parts of the company, and executive chairman acting as a more engaged umpire, ready to make proactive decisions and address issues more frequently. Each role has its ups and downs. But when strategically positioned and holistically aligned, they could create a kind of self-reinforcing harmony in the power structure structure so that the co-CEOs can navigate the complexity of people dynamics more effectively.

Just like Mary mentioned, she likes putting together her own playbook to fit her career and the business. I've still got a bundle of questions and plenty to say about the whole leadership dance. But I'm all ears for what Mary's got coking in her next chapter. And who knows, maybe next round, we'll get Mary and Carson to hop on the podcast with us. All right, gearing up for the home stretch here, let's dive into our interview's final question. The very last question that I ask every single guest coming to my podcast is about their book recommendation. Yeah, so I'll be really honest with you since we're friendly too. I've been doing too many reels and doing the whole device thing before I go to sleep.

In terms of my reading, I do tend to lean more towards the nonfiction. And one book for me that really changed the lens at which I look at the world and humanity, where we are today and where we're going, is this book called Sapiens. And it was written by an Israeli author. Maybe you've read it. Highly intellectual. It's one of the best books and one of the best research books I've ever read in my life. It really helped me understand as humans why we are where we are. What is the role?

What was the role of industrialization in driving us where we are? What was the role of capitalism in leading us to where we are today? And I like to think about what's next for us as humanity. He helped me frame out that larger question in a really well-researched and well-thought-out way. I have so much respect for the author. You're like me, not just about interest in nonfiction, but about how to see the world, money, finance,

which we study a lot anyway, but things that would not only enrich us as a human being, but something that would help us to stay resilient given all the craziness going on in the world is the compass that we all want to hold on to. Thank you so much, Merrick. We have so much to talk about. Not enough. We will continue. Thank you so much, Mary. We have so much to talk about. Not enough. We will continue. Thank you so much, Mary. Well, thank you, Vince. Thanks for having me on the show. And I look forward to catching up with you in person when we're on the same continent together. Thanks again so much. In our next episode, I'll be chatting with a dear friend from her Yale days, Katrina Curry, or as many know her as Katie. Katie and I share a background in risk assessment and measurement, well-trained and developed

through years of working with banks, fund houses, and insurance companies. But when it comes to her career, Katie has taken her understanding of risk to a new level, stepping out of her comfort zone with a deliberate approach. I had spent a lot of years being very focused on outcomes, being very intense and intent about what I'm doing.

I have now moved into a phase of exploration and looking at the various opportunities and being less focused on a precise planned path, but embracing these opportunities. That was a major shift for me. You have to know yourself and know your risk tolerance. Like you said, both the hard and logical decision, but also these intuitive, exploratory, pursuing, exploring outside of my comfort zone. How has Katie navigated these changes, crafting her personal playbook for career development? We'll dive into her journey, uncovering insights and strategies.

Thanks for listening. See you in the next episode.