Liam Roecklein x The Future of Fandom

PointsBet Senior VP of Content Liam Roecklein on How to Improve Your Odds of Winning Fans on Social

by The Future of Fandom

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Improving Your Odds of Winning Fans on Social

Today, on The Future of Fandom, we get to read a few pages from a sports book via a content juggernaut: Senior Vice President of Content Liam Roecklein of PointsBet. and the way it innovates within revenue driven content to grow a responsible, diehard following

This isn’t Liam’s first rodeo when it comes to shaking up an industry via content approach; he was previously the first content hire at Cheddar, and saw the brand through its ascent to the pinnacle of financial media. Now, he has turned his sights to sports gambling as the next space well worth disrupting. And on the show today, Liam explains how they do that at PointsBet with a “Thrill Bill” mentality.

We also talk about how the Company differentiates their content experience across acquisition platforms to win on social, and how to win the newest generations of sports fans who are increasingly fanatic about individual players rather than teams. Seeing as sports gambling is legal in just 12 states in the US, the fandom yet to come isn’t just fantasy, it’s real, and it’s right now.

So, let’s predict the rest with PointsBet and Liam Roecklein.

Connect with Liam Roecklein on LinkedIn:

Read more about PointsBet:

Full episode here:



Liam, thank you for joining me. How are you? Good to talk to you.

Liam Roecklein (01:27):

Adam, it’s awesome to be here. It’s really exciting to chat with you about the future of media. I’m excited to talk with you about all these things.

Adam Conner (01:34):

Yeah, the future is something that you have seen many times before in specific points in history. I will ask about that. And it’s just refreshing to talk to somebody who thinks about content, similarly to me, personally, but similarly to people who actually want to watch it. And I feel like weirdly you don’t see that a whole lot within areas where things trend very quickly, like in sports betting over the last year or two as states have brought it on.


We’re going to talk about all this, we’re going to talk about those definitions of those two F words, future and fandom. We’re going to begin with the move to PointsBet, because you had a pretty sweet deal there for a little while as the first employee to Cheddar, who just blew up business media. I’m sure they have you to thank. What about sports betting, PointsBet, the potential disruption you saw there made you jump when you jumped?

Liam Roecklein (02:26):

Well, what I would say is I wasn’t the first employee of Cheddar, but I was the first content hire. And I was there as the first executive producer, which might as well meant nothing, because there was one of us, so I was doing everything in the content creation. And left six years later as the SVP and GM. And the reason I made the move to PointsBet, is because, like you said at the top of this discussion, I’m tracking the user behaviors. And I’m looking for disruption within the media industry.


And when I look at sports media, I think there’s an unrecognized explosion in growth, in fantasy and sports gambling. And I think you see it everywhere now, it’s going to be even bigger, a 100, a 1,000 X bigger. And I think the content that’s being created for gambling around sports, along with fantasy content, which is related to props, et cetera as well, it’s just not great yet. And I think if there’s a leader and a winner in that space, they will dominate the next 10 years as this adoption happens nationally, with more and more legalization across states. And I’m just really excited to be a part of this.


My background has been in digital and OTT media my entire career. One of my early jobs was with Time Inc and Sports Illustrated and GOLF Magazine. I’ve always been a sports fan. I was a two sport college athlete myself. So this is a little bit of a return for myself, personally, but the reasoning for it is the behavior. I’ve been tracking the data. I see what the consumer demands, and I don’t think it’s being done well yet. I think we can provide it to our customer at PointsBet as we build this content strategy going forward.

Adam Conner (03:59):

So you saw some of this sports betting content, not to call out anybody particular, but what’s the trope in terms of type of content that you sit back and you think, “Really?” That caused this push? Is it just content that’s made with the old style gambler in mind sitting at the horse track? Or is it just this overly broad fan polarization type of deal? What about this content made you sit back and think, “I can do better than this?”

“Well, when I look at the content ecosystem for gambling, it really is dominated by the two extremes. So you have the VSINs of the world, which is an OTT platform that is focused on what I would describe as a historic better. They feel like old men in smoky rooms, in Vegas casinos, talking about lines in an antiquated fashion. And then you have the BR Betting and the Barstool Sports of the world, where it feels like very young, 22-year-old, five leg parlays, it is more viral short form, but there’s nothing in the middle. And that is where we see value.”

— Liam Roecklein (4:27)


I think that’s where most advertisers, most companies see value in that 30 to 50-year-old demographic, where there’s a maturity an interest, people searching for news and information. And what our content strategy will do is bring that news and information, data and analysis to our consumer who demands it. They are watching the games through that lens. Yet, right now it’s being seen immaturely, from a very hyper viral standpoint on social media from the companies that are building with that strategy, and then from an old school matter, which feels like Las Vegas casinos, and it kind of loses the main demographic.


So for us, we think there’s a massive opportunity right in the middle, providing news and information, bringing data and analysis, using the different content acquisition platforms and distribution platforms that are most relevant today, so that is social media, organic search, which is mostly dominated by Google, and then email newsletters. So we’re really looking for that more mature better in the middle of those two extremes.

Adam Conner (06:06):

It’s funny on this show we’ve spoken across many industries, but that finding the middle between those two ends of any spectrum has often been the key in disrupting within that, or maybe even just producing for the first time, where not much has been made to specialize. I think about within, well, the financial world, the difference between your old style just maxed out your 401(k), you moron, and the 18-year-old meme stock, which might be today’s Parlay Piranha. Finding something in the middle, which we’ve tried to cover on this show, has been a specialty for folks.


To bring that to sports betting, I agree, you’re not looking for the 18-year-old necessarily. You’re not looking for the old guy in the smoky casino. You’re looking for a better named Billy. Who’s Billy by the way? Can you tell us about this?

Liam Roecklein (06:51):

So Billy is just a cohort, it’s honestly just an internal metric that we use, and we’re trying to attract a traditionally 30 to 45-year-old consumer, who is going to be betting often on our platform. And really it’s a departure from our competitors, who traditionally have gone for mass consumption. We really just want to delight our customers and when we think about Billy, we think about the sports gambler who really just enjoys the experience. It is our job to provide them with the best product experience, with the best lines, the best sports book experience, and also the best content experience.


And we have just come up with this cohort, and our absolute goal is to delight Billy. We do not look at it through the traditional metrics, and a lot of the content we’ll be providing will be making content for Billy. And what that means is we’ll provide him with the news and information so that he is informed to make his bets.


We will have fun and interesting content that will entertain Billy, and we will also be participating during the live events themselves. Those being the sporting events, so that we are there with live opportunities for Billy as he’s consuming on the television, but also dominating the second screen experience. So he’s on, likely, his, but also her phone, sharing memes, sharing betting opportunities. We want to be participatory in that experience and recognize that that is where the consumer is living. They are as much on their phone while watching a game as they are dedicated to the game.


And I think that’s a dramatic departure that is still not recognized, and is a white space for content creators and different operators. Our strategy will be to focus on that second screen experience to make sure that we are in the conversation that they are having with their group. And that all those groups are Billys, they’re focused on winning at sports gambling, and we’re going to provide that information for them.

Adam Conner (08:44):

So to specialize in content, to make the most entertaining thing possible. As the head of content, you’re sort of the Tarantino of your group, and you’re looking to “Thrill Bill.” Winning on social, then, becomes focusing on that entertaining content, rather than maybe what I’ve seen broadly within sports betting over the last year or two, which have been commercials which start with an offer, join us, become a customer with us. Very acquisition focused, rather than necessarily something, which I don’t know if it’s bringing awareness, but it’s just, well, as you said, delighting.


You and I think agree that winning on social is much better to do through that entertainment medium than by focusing on acquisition first. But I want to know why you believe that within gaming broadly that strategy gets disregarded.

Liam Roecklein (09:39):

Well, I can’t speak for my competitor’s strategy, and what I would say is I can talk for PointsBet. We feel that there’s an opportunity to delight our customers with a top tier product experience along with a top tier content experience. And even our new advertising campaign called Sanctuary features a Billy on his throne in the bathroom, placing bets where he can find a few minutes of silence and of peace, and can do what he believes is fun and entertaining and participatory.

“…for us on the content team, it is our job to recognize that life is hectic, life is stressful for the customers and the segment that we talked about at the top of this call, they’re often busy, they have young families, they have stressful jobs, sports gambling is a relief. It is fun. It is entertainment. But at the same time they want to be informed about those behaviors and those bets they will be placing.”

— Liam Roecklein (10:10)


And it is our role on the content team to do two things, to provide them that news and information, so that they feel informed, so that they’re able to place their bets on either side of the equation and that they are confident that they have done their homework. Which they’re looking for, especially within that middle of the road demographically outlined. And then also for them to have some fun, and to recognize that this is a fun behavior that happens within groups of individuals. To brag a little bit to their friends when they win and then to feel it when they lose, obviously, responsibly.


But I think that’s all of part of what is driving the user behavior we talked at the top, too, is that the experience of consuming sports as a fan is being driven by these fantasy behaviors, along with these gambling behaviors as opposed to just the sporting conversation. And if you look at what is being shared, and we see some of this data now, the gambling conversation is replacing the sporting conversation, in terms of priority, when it comes to the events of a football matchup or a basketball game, et cetera.

Adam Conner (11:35):

So in creating this super entertaining content you can enjoy from any throne of your choosing, at the same time you’re maybe helping Bill get paid a little bit, but you also got bills to pay. Can you talk a little bit about being a revenue-driven content producer within the lens of seeking to entertain and thrill first?

Liam Roecklein (11:54):

Yeah, I mean first and foremost, I think our job is to be authentic to our customer. That is content’s functionality within the business. And I recognize that this is a business, but we truly feel as a company, at PointsBet, that if we provide authentic news and information to the customer, we’re going to do fine, ultimately. And actually our strategy, and maybe you’ve heard about this from other guests on your show, is much more about customer-driven capitalism versus profit-driven capitalism, it’s net promoter score. And we are even grading ourselves on how delighted is Billy versus how much profit can we extract from our customers?


And we found that the most profitable companies, Apple, Amazon, Discover, et cetera, have shifted to this metric. And we really are wholeheartedly diving into, how can we make the best possible experience? And I think on the content team, we really want to make sure that the betters within the 12 states were present. And Louisiana just came online, we’re very excited to be in Louisiana this past week. We want to make sure that they have all they need to participate on our platforms, that they have the information, and that when they get to our platforms, our product is best in class.


And if they feel that way, they’re going to be an evangelist for the company, because they’re going to tell their friends within their groups, “Hey, I had a much better experience at PointsBet. I think you should check this out.” And I think if we do that, it’s kind of like the score will take care of itself. Like the old Bill Walsh metaphor, if we do the little things, if we’re making sure at every step the customer feels like they are listened to, that they have everything they need, not only to function, but also because they’re delighted to just participate, we’re sure that they’ll come and that they will share with their friends

Adam Conner (13:43):

Being where the consumers is, is something I admittedly have heard a lot more rather than the first part of the answer, so I’m glad that you gave me the full spectrum there. And, yeah, Louisiana natives and residents, you got a better book coming to the bayou soon.


Now, I want to switch gears a little bit, because I haven’t been as deeply involved in sports gambling from a customer point of view. In fact, well, I’m guessing the majority of the US really hasn’t, because it’s not there yet in this sense. But something that maybe follows the old gambler smoking in the casino is another stereotype that I’m hoping we can dispel here or at least that you try to dispel as you create content for PointsBet. Which is that, “Well, this is really just a casino, the book is against me, they’re trying to get as much money from me and I’m never going to win.” How do you avoid falling into those, I guess, like negative reinforcement loops and biases as you cultivate fans? My guess is the answer here is going to be in the content, but I have to ask.

“Well, what I would say is that dichotomy I think is toxic, and really what we want to do at PointsBet is to authentically engage with our customers and fans. And whether that’s a traditional content audience, we don’t have all the answers, but we’re going to the best of our ability to provide the latest stats, information, original insights, original reporting that will give our customer and our audience and edge, we hope. And then even we want to make sure that we have best in class pricing. So we’re going to be minus 107, we’re going to commit to being better than all of our competitors in the space when it comes to pricing. And when we’re distributing that from a content perspective, we are outlining on social media our pricing versus the competitors.”

— Liam Roecklein (14:44)


We also have done different promotions. So we’ve had relief on MVP bets for example. So we had a promotion where Russell Wilson, those MVP bets, the betters who bet on Russell Wilson, and hee performed so poorly through the first two weeks, we forgave all those bets, and re-credited those accounts. So, for us, it’s not always about beating the individual as a better, in all regards, we want to make sure they’re enjoying the experience, that they’re being entertained. And we’re going to take different tactics, whether it’s through content, product, pricing, and even forgiveness to make sure that we are delighting our customer. To keep saying it again and again, we need to delight the customer.

Adam Conner (16:06):

Yeah, that’s rare too. I mean that’s not something that I would’ve thought that any sports gambling company would do. A nice gesture, of course. It’s tough if you’re a Denver fan, but that’s the point, maybe you got help. And it’s that kind of thing, whether it be in the content or the promotional or the forgiveness aspect of some of these things, if you know are on the wrong side early, that’s how I would think you grow some of those people who are just interested in the content to consumers, fans, to diehards. And that is what any brand wants. I don’t care what industry you’re in, you’re looking for those diehards.


So not on the exact same note as the last question, but I have to also ask, as you cultivate fans that become diehards, are there lessons that you’ve learned or principles that you keep in mind as you do that, within an inherently addictive industry? Because it’s great if somebody’s just consuming the content and being responsible with it, but you can’t possibly control what they’re going to do after that. So I’m curious how you think about that from the producer standpoint.

Liam Roecklein (17:08):

Well, what I would say is, first and foremost, content’s role is to create that authentic experience. And if we’re doing it right, you’re right, we want out of our million total followers, once we get there to have 10,000 diehards. But I also want to say that to your point on gambling, we want to do it responsibly. And what I’m so excited about joining PointsBet is that since the advent of PASPA and the legalization first in New Jersey and now in the 12 states we’re in, but will continue to be adopted in the next three to five years across the United States, is that we have the tools on our platform to reach out.


We are actively tracking customers who may display problematic behaviors, and we will have them limited to avoid problems. We also have support hotlines that we can direct customers to. So I think versus where the industry was prior to the legalization of gambling, the behavior was happening, I think we’re in a much better place. And I think content’s role is, yes, to grow the biggest total audience, to have those diehards consuming our content, but to encourage at all points responsible gambling, because that is first and foremost in our industry.

Adam Conner (18:21):

Yes, it’s good that you’re a steward of that and I think that, well, I think they’ll have to, but every sort of gaming partner that’s legalized in the US will have to maybe meet your standards on that, always be the best there. And I’m just thinking about, even in the past couple of weeks, listeners, we’re recording this in very, very late September, with the pressures among the creator community and the gaming community where platforms like Twitch have just banned streams that will use services that aren’t at least regulated in America, maybe not even legal in America, gambling, because they recognize that potentially toxic cycle in an inherently addictive industry.


It’s great that you have, whether it’s automated or harshly regulated guidelines in place to weed that out. Because, like you said, you want to build responsible, diehard fans. People who are thinking clearly about it. When Billy thinks clearly, everybody wins.


Now let’s go back to being where the consumer is, because I love talking about this topic with people. You have several different acquisition platforms across PointsBet’s content ecosystem. Within each of those different places, each of those thrones, let’s say, where Billy is, how do you tailor experiences across to ensure that they are seeing something new and different and specific every single time they interact with one of your individual properties?

Well, what I would say is, first you have to recognize the user behavior. And what I would say is traditionally media companies have tried to apply a one size fits all content strategy to diverse distribution platforms. And even within the three distribution networks that I just outlined, organic social media, organic search, email, newsletters, and really we are talking about organic here, there are a lot of different tactics and subtactics that we will employ.”

— Liam Roecklein (19:40)


So first and foremost, we are debuting a brand new studio in lower Manhattan called the PointsBet Studio, where we will record linear shows. But the purpose of those linear shows, as much as I love the linear shows, and they’re going to be distributed on OTT or digital platforms, maybe even eventually on networks, and also wherever podcasts are consumed from an audio only perspective, the real goal of those shows are to reverse engineer different clips.


And what I mean by that are 45 to 60 second clips that we can prioritize on social media. And we will cut that with subtitles in vertical format, really in different frames with different markets that they’re discussing within that to ease the user experience across the platforms. And they will have different cuts for whether it’s Instagram or TikTok or Twitter or YouTube. We have to be very specific to the platform, and employ different strategies and tactics to ensure that they are optimized for consumption on those platforms.


When it comes to search, we’ve debuted a new blog for The Hustle is our brand new text based consumption acquisition channel, and really our editorial publication, it is a newsletter that we’ve partnered with Front Office Sports that is written three times a week right now, but will be expanding to five times a week. That will hit inboxes, where people read their information right around the time they’re thinking about gambling on games.


So right now we’re on Sunday, in the early mornings, before the full slate of football, and Monday, right after, recapping and pushing towards Monday Night Football, and then on Thursday as well. There will be more articles, original reporting as well going to digital. But, for us, it’s about recognizing the behaviors. Individuals who are interested in this space are constantly on social media, and when they’re on social media and they’re interested in a game, they’re using Google to look up information around those games and opportunities to bet on markets.


And they’re constantly, just because of the Billy cohort we talked about, on email, likely for work, but also for pleasure and for community. And using those email platforms and recognizing that these are the acquisition channels that are most relevant is a white space I believe. I think a lot of our competitors are focused on more traditional media acquisition channels like linear television or radio or out of home, where for us we really want to pivot towards where is the behavior, the consumption behavior happening? And how do we provide the best possible experience on those individual distribution platforms, with the tactics I outlined?


You need to make sure you’re optimized and you need to make sure that you’re delighting your customer just from a distribution standpoint, too. Because if you put up any barrier, if it becomes difficult, even a little bit, they will choose to go elsewhere. And my goal and I really look at the future of content is easing those barriers, so that it becomes easy to either read, listen, or watch our content, and then, ultimately, make a decision and use our product

Adam Conner (23:01):

Listeners, you could take the last roughly two minutes of that explanation… First of all, roll this back two minutes and play that again to yourself, and then listen to it and ask, what industry you think that that perspective is from? Without knowing that this is sports gaming. Because let me tell you something that is so clearly different in my mind from the way that, well, just gambling in general has been approached forever. But that specific POV is the same way that education got disrupted in the digital age, that tech has been disrupted forever, that financial sector has been disrupted over the last like six, seven, eight years. This is just the model that is going to win.


And I’m geeking out a little bit over here, because as somebody who builds podcasts all the time, but also has these great conversations and builds almost for the short form, even though it’s in a long form shell, that funnel of engagement and consumption is going to make people like PointsBet win. And it’s what makes Liam one of the experts in his craft.


So I’m thrilled to have that foundation for this final question, which is focused on the future, listen to that alliteration. And I want to ask about it, because, when I think about fans of sport, so different even from where we were 10 years ago, and we’ve talked about this a little bit on the show in a couple different lenses.


Fans who are new are not necessarily fans of their teams where they grew up or their teams where they went to school, I mean they might be, but more so they are fans of players. And this makes for a much different fan in aggregate than somebody who is just a Pittsburgh diehard. So in your mind as a content producer and as a steward of a brand which is not only placing bets on teams, placing bets on players, how does that change your strategy, if at all, across sport to hook this maybe Billy of the future as compared to the stereotype in the smoky Casino? I’d be curious as we round out, how you think of the future in terms of the other F word, fandom?

Liam Roecklein (25:09):

Well, what I would say is, you know started this conversation by saying, why sports gambling? And I was traditionally in financial news, at least in the last six years, even prior to that, when I was with Time Inc, I worked agnostically with content. I worked with Time Magazine and Fortune, Essence, People en Español, I even created content in Spanish. So to me the optimization we just outlined in the prior section is applicable to all the different industries you were touching on, education or gaming, et cetera.


The reason why, just answer your exact question, I came to this industry is because I’m following that user behavior, that fandom behavior that you just outlined, which is with Gen Z, and the even more so with Gen Alpha, which is, obviously, almost in its infancy right now, the next generation coming up behind it. I was the individual, I’m in my mid-30s, who watched six hours straight of SportsCenter, who was a diehard, I’m from the New York area, Yankee fan, and checks the box scores in The Daily News every day.


That behavior is not happening. And we are seeing, through data, a shift in individual fandom, especially with the younger demographics towards individuals. And you could see this on social media, whether you’re a Cristiano Ronaldo fan or you are a LeBron James fan, or to your point on Twitch, you’re a streamer fan as well of your favorite gaming platform. And there’s so many of them, I won’t even name them, because it’s so niche to that specific, whether it’s Call of Duty or FIFA, et cetera. It’s so niche to those individual games.

“I think the future of sports consumption is gambling in fantasy, because when you’re no longer interested in the team, for the team’s sake, I want to see the Pittsburgh Steelers win on Sunday, you are more interested in the games, because they are interesting and they are participatory. I need Juju Smith-Schuster, former Steeler, now the Chiefs, to hit on his yards. I am very invested in watching this game to win my fantasy matchup. I am very invested, even to use that exact example, to see him go over 65 yards as a prop bet this weekend. And that behavior will exist.”

— Liam Roecklein (26:37)


Where watching the games to see if the Pittsburgh Steelers win the AFC North or are positioning themselves to get in the playoffs, is less relevant. I also think you talked about from a strategy perspective, I think it’s actually made the league more popular in the fact that more parity exists, there’s less relevance in terms of dominant teams. You used to see the Cowboys dominate for years on end. We do not see that happening anymore. And I think that’s because of a lot of the measures the NFL and the league itself has taken. But it also is better for the league from a media consumption and the gambling and fantasy behaviors we saw, because it makes it more of a global and domestic phenomenon.


So if I’m in Pittsburgh, I care as much about the Los Angeles Chargers game or the Kansas City Chiefs game because it is equally interesting to me as the Steelers’ game. So from a content strategy perspective, I think we become less localized. We’ve become more national, and we’ve even seen that adoption when we talk about sports gambling on European soccer or different types of match-ups that we’ve seen boom in popularity in this country, in the United States most recently.


So I just am following the user behaviors to wrap this up. And there are not a lot of new fans of teams being born. Of course, they exist and they will continue to persist, but there are much more Aaron Judge fans than there are Yankee fans. And I think if we follow that behavior, if we program to that behavior, we’ll win with media now and in the future.

Adam Conner (28:37):

Agreed. As somebody who is 30, grew up with the SportsCenter bingeing as well, even the new sports that I’ve picked up and watching, since four, five, six years ago, those are sports in which I have immediately gone player first, not teams. Sure, I’m Baltimore born and bred, kind of weird being in Pittsburgh, but I’m an Orioles and Ravens diehard guy. I’ll follow those people forever. But in 2010, I watched soccer for the first time, and I got into it, because I was a big fan of Fernando Torres as the player, not Liverpool, FC at the time. I became a fan of the team, but that was much later.


I’ve been a lifelong Motorsport fan, of NASCAR specifically. And these days it’s just about individual personalities, drivers, not necessarily the team for which they drive. If I were a fan of golf, I don’t know too much about golf, but if I did, I know enough to know that I’d suck on my golf course, but other than that, if I were a fan of an individual golfer, I’d be a fan of the golfer, not the country for whom they play, not the tour on which they play.


So I see that perfectly and now that you say it, yeah, you’re just following the behavior. It’s not that hard folks, just look at what maybe Gen Z, Gen Alpha, look at what you’ve done over the last three or four years, and then build for that.


Liam, I’m thrilled to have learned so much from you here, and I’m just, again, refreshing to talk to somebody on the content side of the game who thinks about this in a similar way to the way I do. I’m glad you are shaking it up in sports gambling. Maybe you don’t wish it, but I wish there were three more you to disrupt other boring industries, because we need more people like that thinking forward.


Thanks for talking about the Future of Fandom with us. And hey, if you’re in one of these 12 states that has it now, folks, you might want to consider PointsBet for your premium content and gambling experience. This is all been an ad! No. Anyway, I’m thrilled that you’ve been here. Thanks so much for joining us.

Liam Roecklein (30:25):

Adam, thank you so much for having me.

Adam Conner (30:29):

Take it from someone who works in content production every single day and has interviewed hundreds of brand leaders on how to do it right, Liam knows his stuff. If PointsBet ends up being the foremost content fixture in sports gambling over the coming years, color me unsurprised. Thanks very much to Liam Roecklein for joining us, and thanks to you, the listener, for exploring the Future of Fandom today.


I’d encourage you to stay connected, so you can do this,, go visit that, you can listen to all of our shows. You can also read along, view clips, things like that. And of course we are across social media too, primarily LinkedIn and Twitter, LinkedIn at LiveLike and Twitter @LiveLikeInc. I look forward to predicting the future again with you real soon. And until then, I’m Adam Conner saying so long and thanks for being a fan.

Written By
Megan Glover
Content Manager
Written By
Megan Glover
Content Manager

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