Lessons From the First Woman to Run a Five-Star Casino
December 21, 2023 Boston Chamber of Commerce
Outside of Las Vegas, there is only one five-star casino and resort in the U.S., and it is right here in Everett, Massachusetts. Even more unique, Encore Boston Harbor’s President is Jenny Holiday, the first woman in Massachusetts to run a five-star hotel and casino.
From Reno to Las Vegas to Atlantic City, Jenny came into this industry first working part-time at a casino, then working for Harris Entertainment as it expanded from 4 to 46 locations when gaming outside of Reno and Las Vegas was legalized. Jenny learned the industry inside and out, and how incentive programs played an important part in their success. She joined Encore in late 2019, shortly before it had to navigate the COVID pandemic. She is now at the helm of an organization that is open 24/7/365 with 3,000 employees.
Last week, Jenny sat down with Rose Staram, the owner and founder of Rosemark Production (a boutique mid-sized event firm) for a fireside chat on her role and the lessons she’s learned along the way.
Here are the five key takeaways from this extremely motivational session:
1. Find Opportunities to Get on the Influencers’ Radar
At the beginning of our careers, or when in new roles, our opportunities to get invited to the table are limited. In a big meeting, Jenny took advantage of a pivotal moment to speak up and explain data that another member of the meeting was asked about and didn’t have an answer for. Sometimes it can be scary to speak up for fear of stepping on someone else’s toes, but when there’s a moment to take a leap and get on the radar of the influencers in the room, sometimes you have to take it. Along these lines, Jenny shared that often “the real meeting happens after the meeting.” She mentioned golf as being one venue where a lot of business decisions and networking happen, and thus why it is something she encourages women to get involved in. She continued, “We can’t always be there, but if you are never there, you’ll be looked over.”
2. Facing Adversity Can Be an Important Confidence Builder
While most businesses would never want to relive and navigate through the COVID pandemic again, the challenges it posed to some businesses helped them realize just how quickly they could pivot and how resilient they were. For Encore, it re-opened on July 12, 2021, after COVID closures and curfews had forced them to operate under five different models, and craft an 80 page “bible” that would serve as a guiding light for the industry at large. As Jenny shared, “casinos are not meant to close, but the COVID curfews precluded us from operating 24/7. When you can figure out how quickly you can pivot, you gain confidence.”
3. Never Delegate Understanding
We’ve likely all had moments of “imposter syndrome” when we feel like we aren’t the best person for the job, or question how we got to where we are. Jenny shared an important tactic to combat this: “competence creates confidence, never delegate understanding.” When you learn your business and know your data and information inside out, you will feel like you deserve to be there. And while many things can be delegated (when you surround yourself with an A team), understanding the business or the data should never be among them.
4. Operate Within the Reality of Where You Exist
This is an important lesson in business, but also in our personal lives; it means taking things at face value for what they are. In many workplaces, this could mean being politically acute and navigating through competing stakeholders and influencers within the organization to work effectively.
One specific example of a reality that Jenny faced at Encore is that the employees collectively speak 54 different languages. This posed challenges at times for employees for whom English was a second language, so Jenny took the initiative to see how many employees would be interested in free English language classes onsite. After three pilot classes, 100 employees have now been through the English program. This is the initiative Jenny shared she’ll be most proud of someday when she looks back at her career because of its ability to transform not only the lives of the employees themselves, but also their families and the guests they serve at Encore as well.
5. At the Early Stages of Your Career, Grow Your Calluses
This is all about building thick skin. As Jenny put it, sometimes you need to have “courageous conversations,” as well as an “ego resilience” for when decisions are made without you, or news is delivered bluntly and not in a politically correct package. These qualities, alongside emotional intelligence and resourcefulness, are some of the most important traits Jenny looks for when hiring.
As we continue to gear up for the 30th Anniversary of our Pinnacle Awards and Women’s Network, we’ll be sharing more inspiring trailblazers like Jenny Holiday who are making strides in our community.
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