Buying in From the Beginning

Sara Masterson, President, Olympia Hospitality

Sara Masterson
Sara Masterson

What initially inspired you to get into the hospitality business?

I grew up on Cape Cod, which is an area that relies heavily on travel and tourism to support the local economy. My first jobs in high school were in resorts and restaurants, and I found that it was an industry that just clicked for me. While each job had its core elements, I appreciated early how dynamic the business is through the diversity of the people I engaged with—both guests and colleagues—and the variety of work that needs to be done. Each day is its own. For a while I thought I might want to teach—my degree is actually in history—but this business had me from the beginning, and I never left it.

Who were some of your mentors or role models and what were their most valuable lessons?

My biggest mentor and role model was my dad. He didn’t have any hospitality experience and knew nothing about the business—he was a newspaper guy his whole career. But he understood people and relationships. He understood how to build connections and meet people where they were; how to balance pride in one’s own beliefs without undermining the viewpoints of others; and, very simply, he put kindness and caring ahead of everything else. He was also my biggest supporter; even if he disagreed with a decision or a direction, he gave my siblings and me space to find our paths and never wavered in his belief in us.

Professionally, I give tremendous credit to the then-COO of a resort property that anchored an early part of my career. Lisa Wohlleib was a model for me in what it meant to be a leader in the hospitality business. She gave me opportunities for which I was honestly entirely unqualified at the time, but she believed in my capacity. Her prompting not only gave me confidence in myself but also to pay forward the idea that we are often our own anchors in what we can achieve. It has been a tenet in my career to default to believing in what people can accomplish if given the right tools and encouragement.     

What’s your outlook for the future with regard to diversity and inclusion within hospitality?

Part of what I appreciate most about this industry is that opportunity is available to anyone who has a genuine interest and care for people and is willing to put in effort. I love that you can walk into an auditorium of hospitality leaders, ask who started as a room attendant, dishwasher, server, or front desk agent to raise their hands, and 90 percent or more of the room will respond. It’s a business that values hard work and learning in the field. That, in some ways, serves as a natural leveler to building career paths for anyone willing to put in effort. Our challenge, I think, is presenting the field as an exciting and fulfilling profession to younger career-minded people getting started. We’re known as being a bit of a transient business, but we are so much more than that.

In your opinion, how is the lodging industry performing in terms of getting women into leadership positions?

I think there are several ways to look at this. Statistically, hospitality has a high percentage of women in the workforce compared to other industries. In fact, in many lodging companies, women make up more than 50 percent of the total team. From that lens, women continue to be underrepresented as a percentage of total senior leadership roles, occupying about 25 percent of those positions. But I do think there have been meaningful trends in closing that gap over the past several years, with additional female leadership in C-suite roles, occupying more podium spots, and growing their influence in the space not just as leaders, but as owners and investors. I also think it needs to be appreciated that one of the great things about the lodging industry is that roles can frequently flex and evolve to accommodate people’s personal needs, so that can often be attractive to women who may be engaged in other interests or demands, including artistic, caregiving, and entrepreneurship.

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