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Growing up on Cape Cod, working in hospitality is practically a rite of passage. And for Olympia Hospitality President, Sara Masterson, not only did this experience early on provide a strong foundation in people skills, it gave her the confidence to allow her inherently curious and compassionate nature to guide her along her career path.
In her 19-year journey with Olympia – both in the field and in corporate—Sara has
proven without a doubt that those skills once considered “soft”, are among the building blocks for a strong leader. Here’s herstory:
Sara, you went to BU to study hospitality management, but shifted gears to study history at U Mass. Curious about what kind of moment that was for you when you decided to pivot?
Yes, I got through my junior year at Boston University, and did very well. I remember calling my parents at the end of the semester and saying, “You know, I don't think I'm going to come back.” My parents, to their credit, were always very open and supportive and said, “Okay, well, let's unpack that. Why after three years, with one year to go, do you not want to do this anymore?” And I said, “The thing is, this is a business that's built on experience––I have that already and feel like my education can be something other than that.”
I had been in the hospitality business since I was in high school––that’s just what you do growing up on Cape Cod, you work in hospitality. And I didn’t feel like I'd given myself enough room to explore other possibilities and avenues, because I did have other interests. They asked if I could just hang in for one more year to get that piece of paper, but ultimately said, “You have to do what is right and comfortable for you and we trust you.”
Having that support from your parents must have been extremely liberating, as well as reassuring.
It was, and so I got through the end of my junior year, then took some time off and worked in the field doing a bunch of hospitality-related jobs. By then I
was in my early 20s and thought, well, I'm ready to go back to college now, but I don't want to study hospitality or hotel management because I'm already learning that in a very real way. But I've always been very curious and interested in history, particularly elements of social history and I love to read so, I re-enrolled in school at UMass, and I studied history.
It was such a great thing for me to do because I was back in school on my terms. It wasn't because I had to or because there was that expectation that you graduate from high school, and you go to college. I wanted to be there and was studying what I loved… something that was interesting to me, that expanded my knowledge and my horizons.
Because I worked full time while I was in school, I learned about discipline and how to fit a lot of pieces into a finite period of time, and I loved it. That was probably the best education experience that I've had.
Do you think having had the experience of working on property in a variety of positions, including General Manager, has contributed to your success as President of Olympia Hospitality?
Without a doubt! As I mentioned earlier, this industry is built on experience. And your credibility comes from what you’ve done before. Have you been the one checking people in and do you appreciate what that looks like? Have you been the one turning over rooms or dealing with an upset guest or having to run the audit shift because somebody had a personal emergency come up? And so, yes, I think that's true, not just of me, but really of the team that we deploy out into the field. We have a relationship with what their goals and their challenges are because we've been there, we've done that. And that's a huge part of this industry generally.
So, when you were working on property, did you ever aspire to, or imagine that you would become President of Olympia or any other hospitality organization?
You know, I don't know if I ever put a stake in the ground and said, this is what I aspire to or this is the pinnacle, or this is where I've reached what my long-term goal is in terms of defining it by a title. The needle has moved for me as I've learned and grown and evolved in my own career and just matured in my own space.
And so, I can't say that I got out of college and thought, okay, well, I'm going to be a president of a hospitality management company. I don't really think I knew enough then to know what that looked like. But my goal was always to keep learning and to keep evolving. I think the inflection point for me was when my leadership skills started to transition almost above and beyond my management skills, and realized I was very comfortable in the leadership space.
I remember instances where I became aware that I was using a skill set that was not something I could define on paper anymore. It wasn't about math or accounting or metrics…it was about leading people and making decisions that leaned into their potential, or where I thought they could go. And I remember thinking on occasion that, on paper this may seem like the course we should be taking, but I believe in something different. It's not necessarily a single moment, but a culmination of moments where you sort of say to yourself, I have confidence in seeing beyond what may be immediately in front of me.
Speaking of family, during your 19 years with Olympia, you found time to raise a family of your own. How did you manage to grow an extraordinary career and a family at the same time?
I've got two kids. My daughter is 17 and my son is 12, and there are times where there's no doubt that it has been a challenge because you’re feeling a little bit divided about where your attention needs to be. But I also really do believe that, as a person, you have a hundred percent to give. And I don't believe in this whole work life balance thing. It's just not realistic trying to give 50 % here and 50 % and keep a balance… it’s going to make you crazy.
There were times when there was a lot of external demand and my career needed to take more than 50%, and it needed to do that in order for my family to be okay. I needed to be okay in my career and my workspace… and then there were other times where my family had something going on and they needed more of my time and more of my attention. So, the pendulum is constantly swinging in your time and your resource allocation.
And I would also just remind people that it's really important that you keep time and resources for yourself, as well, because you can't be good at any of those things if you're not taking care of yourself.
I have a very supportive family…my husband is a teacher, and so his hours definitely worked better for kids who were school-aged. I also think that a lot of what I've done professionally informs how I am at home and vice versa. Not that work and home are the same, but there are lessons learned in each different role we have, whether it's daughter or aunt or mom that inform us in our other capacities.
Has anything surprised you along this journey to where you are?
Yes, I'm still regularly surprised and curious, and I actually think that's good, because I never presume that I know what's next or what's on somebody's mind. I hope I always will be and that I don’t become predictable or try to predict everything that's going to happen.
What are you curious about now?
I'm very curious about photography and not a particular genre of photography, not just street photography or landscape. I take classes across the spectrum because I just love it. I love the way that it makes you stop and be present in the moment, whether that's classes on the streets of Boston or Venice or in my own backyard, in my own garden around the flowers that I'm growing, and the vegetables that we're producing. I have a lot of curiosity in the arts, but photography specifically.
Do you think surprise and curiosity help keep people, and brands relevant?
Yes! We go back to that earlier question of why did I switch from hospitality to history? Well, I wanted to learn something different. I like to learn and have a lot of things that I do outside the workspace because I want to keep stretching and relating to people in different ways.
My dad was a newspaper editor, and he taught us to go into things with an open mind and to listen, not just listen for your next turn to speak, but really listen to people because you would learn a tremendous amount that way. And so, I think that has stuck with me through my career and my personal life. I just like to listen.
Well, based on your career trajectory at Olympia, it’s apparent you found a very supportive culture that recognizes your value…and values.
Oh, without a doubt. I'm pretty determined…I'm pretty focused, and I think those are also important leadership qualities, because I think you have to take advantage of opportunities as they present themselves and learn from all of it…especially the things you do wrong--learning from mistakes. But yes, absolutely, the culture, the support that I get with Olympia has definitely been a major factor in where I've gotten in my career at this point.
I'm pretty determined…I'm pretty focused, and I think those are also important leadership qualities, because I think you have to take advantage of opportunities as they present themselves and learn from all of it…especially the things you do wrong--learning from mistakes.
I think people want to feel as though they're connected to something and they're part of something. People want to count…they want to be recognized. My mom was a high school teacher, and one of her first things every school year was within the first two weeks, she wanted to know every student's name, and not in a passive way, but to actually be able to refer to her students by name…and she had hundreds of them. I remember her saying, people want to be seen, they want to hear their names, they want to count.
That’s not a novel idea…it’s been true throughout our history. And I think that when you can touch on what people's individual impacts are, you get a lot out of them because they feel appreciated and recognized -- it's really seeing somebody as a whole person.
We are a family first organization…a culture focused organization. We're very people centric. And it feels good to work for this group. It's not transactional. It really does feel like family.
Quickfire with Sara
What’s your morning routine?
Try as I might, I am not really a morning person. So my routine is pretty simple: coffee before anything, check in with kids’ needs / activities for the day, and get everyone out the door.
What is your best travel hack?
Buy must-have products in duplicate so that whatever you use at home every day has an exact match already packed for travel. And replenish the travel items as soon as you get home. Not having to think about make-up and other grooming products when preparing for a trip is a huge time and mental energy saver.
What books, podcasts or movies are you into right now?
I love to read and usually have three or four books of different type going at once. Right now they are Leonardo Da Vinci by Walter Isaacson, The Magician by Colm Toibin and East of Eden by John Steinbeck.
What is the best piece of advice you’ve ever gotten?
There are three things we can never get back: time, words and opportunity. Treat each with the care they deserve.
What brings you joy, these days?
So many things! I am very fortunate to have a lot of interests so there is always something in which I can find joy, even when life gets challenging. But my biggest daily joy is my children – at 17 and 12, they are at great ages for travel, sharing ideas and everyday engagement. I love watching them grow into their individuality.
Hear more of Sara's conversation with Nancy Mendelson on Hospitality Daily.