President of Encore Boston Harbor, Wynn Resorts
Search every verified Jenny Holaday interview, podcast appearance, and on-the-record quote — each transcript cross-checked by AI and human review to confirm speaker identity. Jenny Holaday, President of Encore Boston Harbor, has discussed the casino’s operations and community initiatives in several public appearances in 2024 and 2025. She stated that a planned relocation of the poker room was put on hold due to the company’s evaluation of capital projects while prioritizing a large project in the UAE, and that a new slot area is being created upstairs based on customer demand. Holaday noted that Encore Boston Harbor is the single largest taxpayer in Massachusetts and described the resort’s role in serving shareholders, guests, and communities. She also mentioned the casino’s Feed the Funnel food-packing events, which she said occur twice a year and involve staff and community volunteers. Holaday has spoken about her leadership philosophy and the importance of women in the workplace. She described her leadership style as “down” and said she believes great leadership requires both love and discipline. Holaday stated that she pays close attention to the “paradox of power” and aims to avoid becoming corrupted by authority. She said Boston has embraced having more women leaders and expressed a hope that the workplace would eventually focus on “really smart capable people” rather than gender. Holaday also said she is “super conservative” regarding problem gaming and emphasized that the casino should be a form of entertainment that is not predatory or exploitive.
“So, it actually the woman who's in charge of our nonprofit and community relations efforts at corporate, Monica Moradken, brought the Pack Shack to us and it started off small in Las Vegas and then we said we'd love to do it here as well — the cost of living in Boston is so high that food insecurity is a real problem h...”
“In my industry it's very difficult to recruit here because of the cost of living, so my pitch is that having a resort of this magnitude in a city like this is a unique opportunity and if that matters to you it's a no-brainer.”
“I am the primary person responsible for our financial and customer service performance, so yes, EBITDA and our financial performance is a very important part of my job.”
“We think of a host as like your personal concierge — we obviously can't give everybody a personal concierge, 20,000 people walk through this building in a day—so it's a personalized service and a reward for being a good customer.”
“Our plan was to move the poker room downstairs into the closed night shift space — the relocation project was put on hold because of the tariff situation; the company evaluated all of their capital projects while prioritizing a very large project under construction in the UAE.”
“We're creating a new slot area upstairs because customers vote with their wallet — Shake Shack definitely outperformed 'On Deck', so we're adjusting based on customer usage and demand.”
“In Massachusetts we have class 3 slot machines with RNG math and higher return-to-player percentages; New Hampshire doesn't allow class 3 games and uses VLTs or historical horse racing models, so the customer's return rate is different even if the machines look similar.”
“We do tutorials upon request in private salons because convention-center gaming regs prevent doing them there, but a lot of people now learn how to play craps or blackjack online before they visit.”
“Staging a concert in our ballroom costs about $185,000 up front and only fits roughly 1,200 people, so the economics are very challenging — we're also mindful of a 25,000-seat stadium planned across the street and would coordinate rather than compete.”
“I very, very firmly believe you cannot change the core components of your loyalty program once you introduce them. It drives me bananas when they get watered down, all you do is end up alienating your customer base and feeling like they've been exploited.”
“We serve our shareholders for our financial performance and we serve our guests and our communities for the experiences that we create. I take that very seriously.”
“We are the single largest taxpayer in the Commonwealth. Our construction project was the single largest standalone construction project in the Commonwealth. So I know there's a lot of expectation of us, but I don't dwell on it or worry about it because I know we're up for it.”
“I am super conservative when it comes to problem gaming. I don't want anybody to gamble beyond their means. It's very important that we are a form of entertainment and not predatory or exploitive in any way.”
“My primary role as a leader is to create as many livelihoods as I can. That's how a great leader performs. Our success means their success.”
“Great leadership is about love and discipline. I have to genuinely care and love every one of these people and want them to deliver their absolute best. But I also have to be really clear on expectations and boundaries and when we fall short, I have to be tough.”
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