Hotel Business caught up with Sara Masterson, president, Olympia Hospitality, to discuss her career journey, her role at the company and her thoughts on being a female leader in a male-dominated industry.
Have you always been interested in hospitality?
I grew up on Cape Cod, an area deeply tied and dependent on tourism to support the local economy. In high school, some of my first jobs were in hospitality in both restaurants and resorts. From the start, it felt like it was where I belonged. No two days were ever the same. I quickly came to appreciate how dynamic and diverse the industry is, and how ever-changing the nature of the work is. While I was on a path in college toward teaching—my degree is actually in history—I came to realize hospitality has always been it for me. I was drawn in by the energy and never looked back.
What was your first job in the industry, and what did it teach you?
I was a room attendant at a bed & breakfast on the Cape. The rooms were small, with pitched ceilings and barely enough space to get between the bed and the wall on one side. There was no air conditioning, no elevators and lots of narrow, creaky stairs. The work was hard, hot and repetitive. But I still remember the people I worked with. There was a sense of camaraderie in that job that I have found to be true of the industry generally. We worked hard together, and we took care of each other. I would come home exhausted but still looking forward to the next day, certainly not because of the number of times I hit my head on a sloped ceiling making a bed but because of the people. My first job taught me that this industry is about people and relationships, regardless of your position or title.
Have you had any mentors along the way? What did they teach you?
My greatest mentor and role model was my dad. He didn’t have a background in hospitality—he spent his career in newspapers—but he had an incredible understanding of people and relationships. He knew how to build real connections, how to meet people where they were and how to stay true to his own beliefs and values without discounting someone else’s. He led with kindness and compassion first. Naturally, as a reporter, he questioned everything. That curiosity and thoughtful thinking really stuck with me. It has shaped my own approach to decision-making and leadership. He was always my biggest supporter, giving me space to find my own path, even when he disagreed with my decision.
Lisa Wohlleib is someone who really believed in my potential and that made all the difference. She really showed me what it meant to be a leader in hospitality. Her confidence in me helped me build confidence in myself and taught me an important lesson: sometimes the biggest barriers are the ones we put on ourselves. That experience has shaped how I lead and a guiding principle in my career, believing in what people can achieve, especially if given the right tools, support and encouragement.
When I returned to college to pursue history, I had a European history professor, Dr. Gerard Koot, who encouraged my curiosity outside of work and career. His lectures pulled together threads of political, economic, military and cultural change in ways that I hadn’t considered and found fascinating. I remember very few of the names and dates he conveyed, but the social dynamics have stayed with me, and I think have influenced my work in this business that is with, for and by people 24 hours a day, seven days a week. Like my reporter dad, Dr. Koot also taught me to know my sources, not rely on assumptions and. most importantly, to think.
How does your experience as a general manager help you in your current position?
This is an industry built on experience. There are elements that can be taught in a classroom, but the best education comes from operating in the field. It is hard to appreciate the stressors of night audit callouts, broken laundry equipment on a busy Saturday or an entire dining space filling at once until you have experienced it and been responsible for responding to what are the daily realities of hotel operations. I don’t think there is a substitute for it.
In my current position, I need to balance operating sympathies with those of owners and investors, which are not always the same, especially during periods of uncertainty. We need our hotel teams to flex and drive profit while they are understandably concerned about overextending team members or not having resources to perform their jobs. I think my time as a general manager, and really my time before that as a department manager and line-level associate, gives me insight into where we can reasonably push and when we need to be a bit more cautious. I also think it helps me communicate with the property leaders in a way that resonates with them. It is a dialogue, less than a directive. We can find that common ground, even if it is a little uncomfortable for a period, because there is trust and understanding.
What is the company culture at The Olympia Companies and Olympia Hospitality Management?
We are a family-first and values-driven organization. I say it all the time: Our values are not an obligatory poster that hangs on a wall, but are very much part of our daily discussion and decision-making. Fun, concern for others, trust, accountability and continuous improvement are the core elements of our culture, and we live them daily in our engagement with guests, clients and each other. We focus on using them in balance to drive operational performance, support associate satisfaction and create lasting value for our owners and investors.
What are some of the recent projects that have been added to the Olympia portfolio?
This year so far, we have added a collection of independent inns in Edgartown, MA, on Martha’s Vineyard that we are really excited about. And we also added four great hotels, with various franchise affiliations in the Virginia Beach and Norfolk area of Virginia, including a Moxy and an Autograph Collection hotel which are new brand engagements for us. We are very fortunate to have an opportunity to work on high-quality assets with owner and investor groups who are very much aligned with our approach and philosophies.
How did the partnership with Vassar for The Heartwood at Vassar project come about?
Olympia has developed a niche for campus hospitality, both as a management group and through our own development projects. It’s a unique environment for a variety of reasons, and one where we have earned a reputation for performance that aligns with the individual campus goals and mission. Vassar was considering an on-campus hotel, and we got to know them through their journey of evaluating what the Vassar campus community wanted and could support in a hospitality asset. Ultimately their project was driven by a pedagogical mission to create The Vassar Institute for the Liberal Arts, supported by a hotel and restaurant. We officially joined the project team in 2016, and our development company supported the college through design and construction. Olympia Hospitality welcomed the first guests last July 2024.
(Look for more on The Heartwood at Vassar in the April issue of Hotel Business.)
What does the Olympia pipeline look like?
We have what I would say is a comfortable pipeline. As an organization that prides itself in offering high-touch services to our clients and investors, we do not really look for large portfolio acquisitions but projects that will benefit from our style of engaged support. We’ll have a few more third-party additions to the portfolio this year. We are also sselling a couple of assets and will add some owned work as well. It’s going to be a dynamic period, and that is why we love this business.
Can you detail your journey as a female leader in the industry? Have you faced any obstacles? What about opportunities?
Admittedly, it is hard for me to discern the elements of my journey that were unique to being a female leader in the industry; it’s the only lens I know. I can say that it was not unusual, in my career, to be the only woman, or one of very few, in the room, especially as I made early above-property advances in my positions. There are a lot of women in the hospitality business generally, and I have enjoyed relationships with great female leaders throughout my career. But it is obviously also true that the most senior roles are still occupied by men, though that dynamic has started to shift over the last few years.
I think one of the biggest obstacles for me, early on, was simply finding ways to relate to some of my counterparts, who were often men. Our interests were generally different, and I am by nature on the quieter side, which made connecting harder in a business that is really relationship-dependent. This has gotten easier with time but is still something that requires my conscious attention.
However, I think being a female leader in this industry has presented more benefits than drawbacks. Women have a profound impact on our business; more than 50% of the hospitality workforce is made up of women and 80% of all travel decisions are made by women. As I mentioned above, hospitality is a relationship business, and it is a great opportunity to offer leadership with a genuine appreciation of and empathy for the priorities of this group. As a mom, daughter, sister and aunt, I feel the many, often conflicting, tugs on our time and attention; work-life balance isn’t real—it’s a constantly shifting blend. As a traveler, I can speak directly to the importance of good lighting and counterspace; dark bathrooms with small vanities aren’t moody, they are annoying. I see the industry through the eyes of this powerful contingent of our workforce and consumer base. And I have had very good fortune working with a company that not only appreciates that perspective but has encouraged it.
What advice do you have for aspiring female leaders?
It is really helpful to find people along your journey who believe in you and support you. Whether mentors, advocates, family or friends, these relationships are honest sources of encouragement and advice. But the most important relationship you will have is with yourself. The words you say to yourself are by far the most impactful and have the longest effect. You are going to make mistakes (great, you tried something different). You are going to be wrong (awesome, an opportunity to learn). Not everyone will like you (That’s OK, we’re not all meant to be friends). Confidence and humility are not binary; learning to reflect and speak to yourself in a way that appreciates both is an important step toward understanding and embracing your own leadership.
