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Jennifer Weissman
Senior Vice President & Chief Marketing Officer, PENN ENTERTAINMENT INC

: Creating Unified Experiences in Gaming: Jennifer Weissman on PENN Entertainment’s Strategy

🎥 Jun 12, 2025 📺 ADWEEK ⏱ 31m 👁 68 views
How do you market entertainment experiences that span physical casinos, online gaming, and sports betting? In this episode of ...
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About Jennifer Weissman

Jennifer Weissman, Senior Vice President and Chief Marketing Officer at Penn Entertainment, discussed the company's marketing strategy in a June 2025 podcast interview. She described Penn as an entertainment company focused on gaming, operating 42 casinos and racetracks across 20 states, with online gaming under brands including Hollywood Casino, Scorebet in Ontario, and ESPN Bet through a partnership with ESPN. Weissman noted that gambling is regulated at the state level, which affects advertising, and that the company uses the term "gaming" for regulatory ease while using terms like "sports betting" and "casino gambling" with consumers. She stated that Penn has more data than many other companies due to how it tracks customer behavior, which aids CRM and operational efficiency. Weissman said that the average age of Penn's database is 10 years younger than before the company launched sports betting, which she described as providing an opportunity to build relationships with customers earlier in their gaming life cycle. She highlighted Penn's partnership with Ticketmaster for loyalty redemption through the Penplay program, allowing customers to redeem points for event tickets, which she said provides a new revenue stream and enriches customer data. Weissman characterized the role of the CMO and her team as being the voice of the customer, communicating trends and understanding crossover between customer behaviors across different products. She also remarked that people gamble for the thrill and escape, not necessarily to win big, and that casinos are constantly evolving with regulatory changes.

Source: AI-verified profile updated from Jennifer Weissman's recent appearances. Browse all interviews →

Transcript (32 segments)
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Jenny Rooney0:00
If you're going to push back today on the tool we're using, I don't know, to manage our CRM as an example, I really hope between now and the end of your career, you've had the luxury of working with 20 different kinds of tools, right? Because every day we're evolving so quickly.
Hi everyone and welcome to the Marketing Vanguard podcast. I'm Jenny Rooney with AdWeek and I'm thrilled to be here today with Jennifer Weissman. She is the CMO of Penn Entertainment. Jennifer, welcome.
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Jennifer Weissman0:33
Thanks, Jenny. I'm really excited to be here today. Yeah, it's great to meet you. I love doing the podcast because it gives me an opportunity to meet new CMOs and equivalent titles who are doing some pretty cool things. And I would love for you to introduce yourself to our audience and tell us a little bit about Penn Entertainment.
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Jenny Rooney0:47
Sounds great.
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Jennifer Weissman0:55
Well, you introduced me. I'm Jennifer Weissman and I'm the CMO at Penn. I've been with the company since 2015. Before that, I was with Caesars, which originally was a company called Harrah's Entertainment. I'm originally from Memphis, Tennessee. And unless you are really in love with Elvis, there's not a ton of marketing jobs within the city. At the time I was really looking to get into marketing, I had moved back home to Memphis from where I went to school and casinos had just popped up in Tunica, Mississippi, which is about 45 minutes from Memphis. It's amazing to think now, but at the time, Tunica was the third largest gaming location in the entire country, just behind Las Vegas and Atlantic City. There was Tunica, Mississippi where the cotton fields were. So I found myself working in public relations for casinos about 45 miles from Memphis. From there, I took on various different marketing roles at Harrah's and then eventually Caesars before I moved to Penn in this role. At Penn, we are an entertainment company primarily focused in the gaming space. We run 42 casinos and racetracks across the country in 20 different states. We are also really robustly focusing our efforts in online gaming and do that under three different brands: Hollywood Casino, which we operate in New Jersey, Pennsylvania, Michigan, and soon West Virginia; we also operate under the ScoreBet brand in Ontario, both a sportsbook and an iCasino; and we also operate ESPN Bet with a great partnership that we have with ESPN in most of the states where sports betting and iCasino are legal in the country.
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Jenny Rooney3:18
Okay, so I have to kind of laugh when you use the term gaming because in the marketer community that can mean very different things. I mean, just having nothing to do with the sort of gaming that you've traditionally been involved in. I'm just curious, what do you think about the rise in gaming in terms of virtual reality, digital gaming, all those kind of virtual worlds type gaming and the competition gaming that we're seeing that happens remotely, as that has risen up in recent years clearly as a huge branding opportunity, big vehicle, but again the nomenclature is used to assign to something else. I don't know, from where you sit, given your area of expertise and your passion, how you claim or think about gaming. Does that benefit you? Does it distract from what you're doing? I'm just curious.
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Jennifer Weissman4:04
It doesn't distract at all. In fact, I think that it really speaks to the point that people in general are competitive regardless of whether or not they're doing it for money or they're doing it for a trophy or they're doing it for a title, or they're doing it for virtual badges, or like my children remind me every day, who are 12 and 10, for new clothes that their avatar gets to wear. So there's this innate thrill that really comes with gaming in general. I think it's funny that you point that out. It probably ages me quite frankly because when we started, or when I started, and casino gaming started proliferating across the US, there were a lot more laws around how we could refer to the experiences that we were offering. Gambling is regulated at a state level, which means all of our advertising is also regulated at a state level. So this term gaming seems to kind of fit easier across most of the jurisdictions we're in. Although for the most part today, when we're speaking to consumers, we really differentiate our experiences and utilize the terms sports betting, sports gambling, casino gambling, slots, table games, and we are more specific because we can be. But truly, when gaming, and I'm using quotes so people won't be able to see it, but when we first started advertising, we actually couldn't even show the casino floor, or we couldn't show people on a slot machine or a table game, we couldn't show that thrill of the win. And now we can. So I do think gaming in general is just this innate nature that a lot of us have, and other kinds of companies have figured out really how to leverage that in other ways, virtually, in person, and the like. But yes, I see it as a great adjacent business quite frankly.
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Jenny Rooney6:30
Yeah, for sure. And again, as I mentioned before, that's just so fascinating. I love you flagging that because I do think your ability to weave and actually share the similarities more so than the differences is key. And it's about consumer insight and understanding and that drive for competition, right? It has made for certainly in the online digital gaming, the virtual gaming, a lot of marketer brand marketers in recent years have sought that out as a branding vehicle because it's high engagement, right? So if it's like in-gaming ads or actually creating having the brand be part of the virtual world, I guess what I'm saying is, or what my question is around, do you also think about that from your vantage point in terms of how you can create new and additional and diverse opportunities for advertisers who come into your space? What are the engagement mechanisms that you're seeing or providing? What is the nature of the dynamic now in terms of advertising in your gaming space?
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Jennifer Weissman7:40
Yeah, I think that's a really great question and I see it in a couple different ways. One, I see it with businesses. So take our business out of it, but just general businesses. Companies that do a really good job with engagement have figured out how to gamify the loyalty experience and do that within their own apps, and they're not even necessarily doing it externally with paid advertising, but they're doing it within the audiences that they already know. So I think about companies that I engage with all the time: Starbucks, Coffee Bean and Tea Leaf, Target. They give me hurdles that I need to meet, which really is they give me dollars I need to spend in order to feel really good about myself and unlocking more dollars that then I can spend with them. So gamifying the loyalty experience has been something that companies have started to do really well. We've been doing that for years with tier programs in our loyalty space and giving people hurdles to hit in order to unlock greater value when it comes to service, experiences at the properties, more personalized kinds of offers and rewards, and quite frankly gifts that no one else gets. From an advertising standpoint, I was talking to someone before, maybe we were going to talk the last time, and something was popping up in my Facebook feed that I thought was super interesting and was a lot about brand placement. I also think a bit about the experience in gaming, and that was with White Lotus. I was noticing that I could get White Lotus sunglasses. Never had I seen that in my Facebook feed, but I thought, 'Oh my goodness, what a great way for this company to build a brand partnership and create a different kind of experience that feels a lot like I'm in the streaming.' And it's very personal because most people are not watching White Lotus on a large screen, right? They're watching it on their iPad or on their phone. And now your ads are communicating to you about the things that you enjoy streaming. So I think there's lots of implications about how to bring in that experience and make it feel like it's fun, experiential, and it's adding to your overall experience. So gamification in general, whether it's in entertainment, the way that you're asking people to behave with the way that they are buying your product, I think is a big motivator for people. We talk a lot about the fact that people aren't gambling because they think they're going to win something really big. They're gambling because they love the thrill of the game. And they like to do this with their entertainment dollar. So they're looking for what a lot of times we call time on device. They really just want to spend a bit of time away from the everyday and have that escape. And now we're able to offer that in multiple ways, which also leads to the more immersive aspect to what we're able to offer today than what we were in the 90s when I first started the business. People are coming into our casinos physically, but then they also have the ability in states where it's legal to have a short respite from the everyday and gamble virtually, which is what we're seeing a lot of people do with games.
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Jenny Rooney11:51
Yeah. I mean, to borrow a tired phrase, but it's true. It's not the destination, it's the journey, right? So what I'm hearing is the journey of the game is what people keep coming back for, and that's what they crave, and that's what is being satisfied when they're engaging with the game.
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Jennifer Weissman12:09
Yes, that's right. The stories, the noise, the experience of the win, even if it's small and not huge, it's the overall experience for sure.
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Jenny Rooney12:22
Love that. So talk about Penn Entertainment itself. Is that a consumer-facing brand or is that the parent company that oversees all of these other?
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Jennifer Weissman12:28
It's a great question. Penn Entertainment is really much more of a corporate brand. Our consumer-facing brand that falls underneath the parent Penn Entertainment is Penn Play. Penn Play is our loyalty program and it's what I call the lifeblood that runs through all of our individual products, and it's the way that we try to really engage customers throughout our ecosystem consistently and to maximize the consumer value from one product to the other so that you're always earning toward a higher tier which unlocks better service, a higher tier that unlocks more recognition, a higher tier that unlocks box-like gifts and personalized kinds of offers. And by the way, that's not unlike, I mean my mind goes to hotels, my mind goes to Marriott Bonvoy, which does a phenomenal job with this, and it's very similar. So Penn Play is what I would consider to be our consumer-facing brand underneath the parent, and then the primary brands that people are interfacing with and really have that experience with are the brands like Hollywood Casino, ESPN Bet, L'Auberge, some of the more individual products that people are interfacing with on a daily basis.
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Jenny Rooney13:57
So it's interesting, I have to ask because it is your specialty as a marketer. It's very niche, right? It's very sort of unique and it's an industry, it's a product, it's an experience that is very unique. And I mean we see CMOs moving different categories from time to time, but tell me a little bit about your educational background. How did you actually always know you wanted to go into marketing? You told me how you ended up kind of in the casino business basically, but what educational background did you bring to bear to now be in this role?
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Jennifer Weissman14:35
It's a great question. I'll start with the fact that I am a daddy's girl and I was always going to follow in the footsteps of my father who is an attorney, but started his education as a journalism graduate. So I went to the University of Maryland. I graduated from the journalism program with an emphasis in public relations. I loved work. That is what I enjoyed more than anything. So while I was in school, not only was I working as a paralegal because I was going to go straight to law school after college, but I also was working various different PR internships. Two of which were in Memphis. One was working with an agency that was trying to get gaming passed in the state of Tennessee. We failed and really just ended up being in Mississippi and now Arkansas. And then I ended up working for another company that did a lot of real estate development and also had relationships with the casinos. So I decided after the internships again that I was just so in love with work I couldn't see myself in school for another several years right after graduation. And my father, being the father that he is, said, 'I never really wanted you ever to be an attorney, don't do what I'm doing.' And so I never got that pressure after to do that. So I started working in PR pretty much right after college. And then I would say about six years into working with Harrah's and Caesars, I ended up going back to school to get my MBA at Northwestern. I was fortunate enough to be able to do that and work at the same time. So that really is my educational background. But I would also say that the reason, unlike a lot of my friends who, unless they've ended up being doctors or lawyers in really more specialized kinds of industries, have changed companies and jobs significantly more than I have over the last 20-30 years, is because casinos are constantly evolving. Regulatory changes every day which gives us more opportunities to find new revenue streams in some cases. Other cases it makes things more challenging or increases our taxes and we've got to find new ways to operate. The casino space in general is kind of like a microcosm. I mean if I want to get really good at food and beverage marketing, I can spend my time there. If I'm really excited by the data in CRM, we have more data than many other companies because of the way that we track our customers' behavior. If I'm interested in operational efficiency, that is something that is really important in the space as well just given how capital intensive the business is and the number of people it takes to service our customers. So it's really been a very evolving career. Each year is different than the next. And that's been able to really keep me interested. And I would say that getting an MBA is very interesting to me because business, and I'm sure given what you do and you're talking to people in different industries every day, business changes. The climate changes every day. But an MBA is one of the fewest really higher degrees that doesn't require a refresh. I think about my father who's an attorney. Every year he has to go back to school to get new credits. Every year a doctor is going back to school to keep up with their license. MBAs don't. So I think it's really incumbent upon us who have gone through that process to continue to learn, to continue to evolve, and to continue to push our thinking forward and to learn from other industries.
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Jenny Rooney18:58
So like you had said, it's a niche industry. It definitely is a niche industry and I mean that in the best way, by the way, because somebody recently said to me in the context of publications, like we're seeing the nichification of publications and publishing. General interest, it's almost like it starts to lose relevance and everybody wants relevance now, right? So you have this specialty that is highly relevant to a hugely unique industry. And yet to your point, which is fascinating and it's an education for me, the variability in opportunity for you is baked into the industry itself, right? Just by nature of the kind of offering that your entertainment provides people.
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Jennifer Weissman19:42
I think that's right. And I also think it's incumbent upon the person because it's very easy in all industries, I think, to get comfortable in a process, to get really comfortable in a tool. You don't have the luxury of getting comfortable. I just don't think anybody should. And I've mentioned it to a couple people actually along the way that if you're going to push back today on the tool we're using, I don't know, to manage our CRM as an example, I really hope between now and the end of your career you've had the luxury of working with 20 different kinds of tools, right? Because every day we're evolving so quickly. So I do think the education is important. I'm really lucky to have been able to go to school the way that I did. But I also think it's incumbent upon all of us to learn every day and to find implications to improve our businesses from others in the way that others have been able to find success.
J
Jenny Rooney20:53
How do you define CMO impact? That's an oft discussed concept, but I'm really curious what's Jennifer's view of that.
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Jennifer Weissman21:04
I think that the way that I see myself and the role of my team is to really be the voice of the customer. And if we're doing a really good job of communicating trends, of communicating the things that are important to our customers today, the crossover between their behavior in one product and another so that we can unlock more value, that is where I see the most important impact of the CMO role in my organization. Because there are distinct businesses that are running online, there are distinct businesses that are running casinos, there are distinct businesses that are running racetracks. But where a corporate organization that is managing all of these businesses derives more value is when we can understand the value that each of those products provides on a daily basis to that individual person, or where it doesn't, so that we can find that opportunity and unlock it the most.
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Jenny Rooney22:16
News on the horizon for you all. Listen, we're AdWeek. We always love to sort of break news and share the latest and greatest from any given marketing company. So tell me what's on the horizon for Penn.
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Jennifer Weissman22:27
We had two new casinos that were going to be opening, one in Joliet, Illinois, and one in Aurora. So I'm going to be spending a lot of time in the Chicago area. I'm really excited about it. I would love to break the news about all of the food and beverage offerings, but I will say that we have announced that Giada is going to be one of the chefs that we're going to have a relationship with at both properties and are thrilled to be partnering with her. And we will be announcing some other relationships that are really popular in the Chicago market that we're excited to really bring to the suburbs and to bring customers that we already have in the Chicagoland market to give them new and interesting experiences. So we operate two older what we would call sort of riverboats and those are going to be closing and transitioning into these new land-based casinos with really varied experiences unlike those that we've been able to provide to date. So really excited about that. We're also continuously opening new ESPN Bet sportsbooks, and they're typically sportsbooks as well as dining experiences, game watching experiences across the enterprise. So more of those will be opening across the company, a great way for us to really bring to life the online experience within our casino for those consumers that really like the sports betting experience. That skews younger, by the way, definitely skews younger. So one of the things that we've noticed over the course of the last really since the pandemic up till now is the average age of our database is 10 years younger than it was before we launched sports betting. So the great opportunity that sports betting has provided us is really an opportunity to get to know people and build a relationship with them much earlier in what I would call a gaming life cycle. Now we have something of interest to them before they turn 45, 55 and maybe have the time and the money for the physical casino. So we've been able to increase the lifetime value of our customers and relationships that we have with them. And then the last thing I would mention, while it's not necessarily new news, but I think it is highly differentiated and something that I'm really proud of and will continue to evolve and there will be more, is a relationship that we have with Live Nation. So we are the only casino provider of Ticketmaster loyalty redemption. So customers that have a relationship with us and have engaged with our loyalty program, Penn Play, have the ability to use the points and the cash that they're earning in the loyalty program to redeem for Ticketmaster tickets, whether it's a sporting event or to see Taylor Swift. So that is very unique and it is something that we're the only ones in the space that have been able to develop that kind of partnership and we'll continue to have more of those.
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Jenny Rooney25:44
Yeah. I listen, collaborations are everything, but for you, the collaborations are utility for the consumer.
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Jennifer Weissman25:50
It's critical. And for us, it's so important I think for two reasons. One, Ticketmaster has a relationship with so many consumers. So it also is providing us not just more information from a data standpoint on the customers that they know and we know because we're able to enrich the information about those customers that we can match with Ticketmaster. But it also is providing us a new revenue stream of new customers, and then it provides more value when they're not in our building because not all of our casinos are created equal. Many of them have resort-like experiences, but some of them have a quick serve restaurant or a sports bar and not necessarily the most elaborate kind of amenities simply because of where they might be located, the size of the facility. But providing that external sort of thing that people do within their everyday as an option is a huge benefit for us.
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Jenny Rooney26:54
Last quick question, Jennifer, that I ask of everybody is who's next? Who's somebody that you admire as a CMO or equivalent title at some other brand? You can know this person really well or it can be somebody who you admire from afar just because of the unique and exciting work that they're doing for the brand. But who should I invite to have on the show?
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Jennifer Weissman27:20
Oh, I think that's a really good question. I don't know if I have a person. How about what brand inspires you?
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Jenny Rooney27:28
Yeah.
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Jennifer Weissman27:32
So a brand that really inspires me, and this may not be very exciting, but I find it exciting, is a brand called Primary. Primary is a children's clothing brand. And what I find really exciting about it is there was a point in time 12 years ago when I first had my children and I was always looking for some kind of clothing that was just basic. It didn't have a whole lot of thrills. It didn't have big logos across it. It was plain, but also I felt good about washing it over and over and over again. And I could mix and match. It was a problem I was trying to solve in my brain. I don't know why, but because this was my hobby for a period of time was dressing the kids. And then all of a sudden this brand popped up on my social feed called Primary. And now what I love about them is one, they do exactly that. They're just all about basics. Basic colors, basic stripes, basic shapes. No writing, no big branding, but very basic clothes. And the marketing is brilliant. Whenever they communicate with me, it sounds like they're talking just to Jennifer Woodward because that's my name in private life with my kids because that's my kids' last name. They know exactly what, and they've aged with us. So they continue to sell clothes now for kids who are larger as my kids have gotten bigger, and I feel like I've been on this journey with them. I think that it is brilliant. And they were one of the first companies too I noticed to really create an amazing experience when you open up the packages. It was bright. It was colorful. And they had a nice note that was just really impactful and kept me in this cycle of ordering plain t-shirts.
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Jenny Rooney29:38
I love that. And I feel like this is a question I'm going to ask of everybody moving forward is in addition to who's next, it's what brand inspires you? Because I just feel like we find inspiration from so many different things. And especially as CMOs, it's so great to be in your swim lane, but to be able to look over this way, that way, and see brands like that that are just doing some pretty incredible and unique things. Massive opportunity for inspiration.
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Jennifer Weissman30:06
Yeah. And they found me, I mean, somehow, too. And that's what was so interesting. It's like, how did they put it all together and find me? But they did. Personalization, all the things.
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Jenny Rooney30:20
Jennifer, it's been a pleasure. I'm going to go look up Primary. And in the meantime, I'm so happy to have gotten to know you and to have gotten to know Penn. Super cool things you're doing. I look forward to staying in touch and I hope we can continue the conversation another time. But thank you so much.
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Jennifer Weissman30:33
Thank you so much, Jenny. It's been wonderful.
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Narrator30:40
Thank you for listening to Marketing Vanguard, part of the AdWeek Podcast Network and Acast Creator Network. You can listen and subscribe to all of AdWeek's podcasts by visiting adweek.com/mpodcast. Stay updated on all things AdWeek Podcast Network by following us on Twitter at AdWeekPodcast. And if you have a question or suggestion for the show, send us an email at [email protected]. Thanks for listening.