Her Story
About Jolene
I've been in hospitality since 2009, when I started managing a family house in Vermont that grew into managing three properties for friends. This eventually became a full-time career after I owned and operated a bed and breakfast and restaurant in Vermont for about 8 years - an experience that taught me more than anything else, though we had to close it due to having young children and another on the way. In 2023, I became Director of Operations at Vacation Hospitality, where I run the entire company. We manage properties all over the country - Vermont, Massachusetts, Maui, California - and even have a property in Greece. I manage staff in all those locations, including maintenance people, cleaners, and on-the-ground administrators, plus our Vermont office team. My responsibilities span staffing, marketing, bookkeeping, and physical maintenance. What makes us different from competitors is that we work across half a dozen booking channels and coordinate with vendors to deliver what I call a luxury experience. I'm incredibly proud that we have 361 5-star reviews on Airbnb alone, with less than five 4-star reviews and nothing below that - we've been recognized across every booking channel we're on. Before hospitality became my full-time focus, I worked in finance, consulting for banks, but that work was unsatisfying and on the decline. Making the switch meant a big hit to my paycheck, but I don't obsess about money anymore - I make plenty, I enjoy my work, people are happy, and my clients are super happy. Every day, people send me pictures of themselves in our units, on the beaches, water skiing, enjoying themselves, and that really makes me happy and glad to come to work.
Her Interview
Ten minutes with Jolene
01What do you attribute your success to?
I attribute my success to differentiation through quality. Our product is of the highest quality, even though some of our properties are not always the best in the market. Our reviews and responses are what set us apart - we've repeatedly had people stay at other properties and always come back, not necessarily because of the property itself, but because of our staff. I try to manage a lot of the messaging myself, though other staff handle it too, but we all do it with a very consistent, low-touch but immediate response - 24 hours coverage. Half of our business is in Maui and our office is here in Vermont, but we always have coverage, so if something ever goes wrong, we're immediate. I would say our product is differentiated because we give a very luxury experience and make sure that people are happy.
02What’s the best career advice you’ve ever received?
The best career advice I ever received is that there are three things to look for in a job that will make you happy in that job. One is to do something that you just like doing. Another is to do a job that you're constantly learning and improving - that quality of improvement. And the third is to do something important, something that's good for society, like curing cancer, working at a hospital, making people healthy. You don't need all of those - you just need one. If you have one of those things, it's enough to keep you there. And honestly, I've got all three, to a lesser extent on the importance - I'm not curing cancer - but every day, I have people who send me pictures of them in our units, on the beaches, water skiing, enjoying themselves. It really, really makes me happy and glad to come to work.
03What are the biggest challenges or opportunities in your field right now?
The biggest challenge in my field right now is regulation, absolutely. There's a tremendous effort in government, as well as in the hotel industry specifically, to end us and to tax us out of existence. I can't tell you how many locales that we're located in where they're trying to make it so difficult for people to rent their homes.
04What values are most important to you in your work and personal life?
The value most important to me is empathy. You can't have it professionally if you don't have it personally. If you have empathy in our business, you have it for our clients and for our guests. Money is not the point, I think. For example, I had a disaster with a guest where the driveway wasn't plowed and there was nowhere for them to park. The client couldn't have been bothered with it, but we paid out of my personal funds to have someone do it, and we never got refunded for that. But it's that kind of thing - it's not about money, it's about people.
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