The CMO of PENN Entertainment has spent a career learning what actually pulls people back to the casino floor - and the app - and it is not what most people assume.
Ask most people why anyone walks into a casino and they will tell you the same thing: the money. The big win. The life-changing number on the machine. Jennifer Weissman has spent a career inside that business, and she thinks the whole premise is wrong. "People aren't gambling because they think they're gonna win something really big," she says. "They're gambling because they love the thrill of the game, and they like to do this with their entertainment dollar." It sounds like a small correction. It is actually the difference between a marketing strategy that disappoints most customers most of the time and one that keeps them for years.
Weissman is Senior Vice President and Chief Marketing Officer at PENN Entertainment, the company behind more than 40 casinos and racetracks across North America, plus a fast-growing online casino and sports betting operation. She runs marketing for all of it. If you have ever earned a point on a casino visit, gotten an offer that felt oddly well-timed, or downloaded an app because the brand on the building already knew your name, you have met her work whether you realized it or not.
Weissman did not set out to sell gaming. She started in public relations at a casino near Memphis, coming out of a journalism background - a storyteller before she was a marketer. That order matters. She learned to find the human angle, to figure out what a person actually cared about, before anyone handed her a budget and asked her to move numbers. Plenty of marketers spend their whole careers trying to reverse-engineer that instinct. She had it first.
From there she climbed through property-level marketing roles at Harrah's, including Harrah's Tunica and Harrah's St. Louis, then spent more than 17 years total in casino marketing at Caesars Entertainment. Near the end of that run she was a Regional Vice President, responsible for the marketing of nine casinos and hotels that were geographically scattered and competitively very different from one another. Nine properties is nine sets of local customers, nine competitive maps, nine budgets. It is where you learn that there is no single "casino customer" - there are hundreds of overlapping ones, and the job is to see each of them clearly.
Fig. 1 — Weissman moved from telling one property's story to owning marketing for an entire portfolio. Bars are illustrative of scope, not exact tenure.
She joined PENN around 2015, back when it was still known as Penn National Gaming, and has spent close to a decade there. The company she markets today looks nothing like the one she joined. In that stretch, PENN went from a collection of regional casinos to an omnichannel operator: retail properties you drive to, an online casino you open on the couch, and a sportsbook you check during the game. Three very different ways to spend an entertainment dollar, often by the same person on the same weekend.
Most companies would treat those as three businesses with three marketing plans. Weissman's central bet is that they are one relationship with three doors. The customer who plays slots on a Saturday, books a hotel night, and taps a bet during Sunday's game should not feel like three strangers to the brand. She has said her job is to make those experiences connect - to meet people wherever they choose to play and make it all feel like the same PENN.
That line is easy to nod along to and hard to live by. In a company of roughly 24,000 people, being the voice of the customer means constantly arguing for the person who is not in the room - pushing back on the campaign that is convenient for the org but confusing for the player, defending the experience against the quarter. It is unglamorous, and it is most of the job.
If there is a single object at the center of Weissman's strategy, it is a loyalty program called PENN Play. She does not describe it as a rewards scheme or a points ledger. She calls it something more anatomical. "PENN Play is our loyalty program, and it's what I call the lifeblood that runs through all of our individual products." The card - now largely an app - is the thread that lets a casino visit, a hotel stay, and an online bet all belong to the same customer story. Without it, PENN is a set of unconnected venues. With it, PENN is one place a customer keeps returning to.
Weissman is also blunt about what makes loyalty actually work, and it is not the size of the discount. "Companies that do a really good job with engagement have figured out how to gamify the loyalty experience," she says. It is a sharp observation from inside the one industry that already gamifies everything. Her point is that the game around the game - the tiers, the status, the surprise-and-delight, the sense of progress - is what pulls people back, more than any single reward. The best loyalty programs are games pretending to be spreadsheets.
Fig. 2 — A reading of Weissman's public comments: entertainment and loyalty do the heavy lifting; the jackpot fantasy does far less than outsiders assume.
One example she likes to point to shows how far she is willing to push the definition of a reward. PENN, she notes, is "the only casino provider of Ticketmaster loyalty redemption" - meaning members can turn their play into tickets to concerts and events, not just casino credit. That is a different kind of value. A discount saves you money and is forgotten by Monday. A night out is a story your customer tells their friends. Weissman would rather give people the story.
Marketing a regulated, fast-moving business has made Weissman allergic to complacency. She has watched the industry go from paper players clubs to real-time apps inside a single career, and she is direct with her teams about what that demands. "If you're gonna push back today on the tool we're using to manage our CRM," she has said, "every day, we're evolving so quickly." Translation: get comfortable, and the ground moves under you. The people who lasted through the shift were never the ones with the best playbook from five years ago. They were the ones who refused to get attached to it.
That restlessness shows up in how she builds a team. She keeps it to four words. "I encourage my team to be collaborative, curious, transparent and authentic." What is notable is the word missing from the list: certainty. In a business changing this fast, curiosity is not a personality perk - it is a survival skill. The safest-sounding sentence in the room, "this is how we've always done it," is the most dangerous one on her floor.
Step back and the arc is unusually clean for a C-suite story. A journalism student learns to find what a person actually cares about. She carries that into casino PR, then property marketing, then regional command, then the top marketing seat at a company doing billions in revenue. At every level the skill is the same, just aimed at a bigger canvas: figure out what the customer is really there for, and build everything around that answer instead of the one you assumed.
Her answer - that people come for the thrill and the experience, not the payout - is why she invests in retention when much of the industry is spending to acquire, why she treats a loyalty card as connective tissue rather than a coupon, and why she measures success in lifetime value rather than one-time sign-ups. It is a patient philosophy in an impatient business. There is no launch party for improving repeat visits. But over a decade and 40-plus properties, the small compounding stuff wins.
The best summary of Weissman might be the thing she keeps circling back to in interviews. Not the campaigns, not the tools, not the org chart. The customer. She wants to be the person in the building who never forgets why they showed up - and it turns out the reason is simpler, and more human, than the jackpot on the screen.