SHERIDAN, WYOMING – Mar. 6, 2025 – The hospitality industry is as dynamic as it is demanding, drawing passionate individuals who thrive on building connections and creating memorable experiences. Sara Masterson, President of Olympia Hospitality, is one such individual who found her calling in this ever-evolving business from an early age.
A Passion for Hospitality from the Start
Growing up on Cape Cod, an area deeply intertwined with tourism, Masterson was naturally drawn to the hospitality sector. "My first jobs in high school were in resorts and restaurants, and I found that it was an industry that just clicked for me," she shares. Although she initially considered a career in education, her love for the dynamic nature of hospitality kept her engaged. "Each day is its own," she adds, emphasizing the variety of experiences and people that made her stay in the industry.
Mentors Who Shaped a Leader
Every successful professional has mentors who leave a lasting impact, and for Masterson, her father was a significant influence. Despite lacking direct hospitality experience, his wisdom about people and relationships left a profound mark. "He understood how to build connections and meet people where they were," she recalls. His ability to balance his own beliefs while respecting others' viewpoints, coupled with his unwavering support, shaped her approach to leadership.
Another key figure in her journey was Lisa Wohlleib, then-COO of a resort property. "She gave me opportunities for which I was honestly entirely unqualified at the time, but she believed in my capacity," Masterson says. Wohlleib's confidence in her abilities instilled a philosophy that has guided Masterson throughout her career: the belief in people’s potential when given the right tools and encouragement.
Diversity and Inclusion: The Future of Hospitality
Masterson highlights the hospitality industry's unique characteristic of providing opportunities to individuals from all backgrounds. "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," she notes. Many industry leaders, she points out, started as room attendants, dishwashers, or front desk agents, proving that success in hospitality is rooted in dedication and hard work.
However, she acknowledges the challenge of portraying the industry as a viable and fulfilling long-term career choice. "We’re known as being a bit of a transient business, but we are so much more than that," she asserts. Bridging this gap and attracting young talent remains a priority for the industry moving forward.
Women in Leadership: Progress and Opportunities
The representation of women in leadership within the lodging industry is steadily improving, though challenges remain. "Statistically, hospitality has a high percentage of women in the workforce compared to other industries," Masterson explains. Despite this, women still hold only about 25% of senior leadership roles.
Encouragingly, she notes an upward trend in female leadership in C-suite positions, ownership, and investment roles. "There have been meaningful trends in closing that gap over the past several years," she says. Additionally, she emphasizes the industry's flexibility, which allows individuals to tailor roles to their personal and professional needs. "That can often be attractive to women who may be engaged in other interests or demands, including artistic, caregiving, and entrepreneurship."
Conclusion
Sara Masterson’s journey underscores the hospitality industry’s ability to cultivate talent, reward hard work, and foster an inclusive environment for those passionate about service. From learning the ropes at a young age to becoming a leader in her field, her story is a testament to the industry’s potential for growth and transformation. As she and others continue to shape its future, the lodging sector is poised to welcome a new generation of leaders who, like Masterson, buy in from the beginning and never look back.
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