By Karen D. Lorentz
The ski industry is rife with workers who began as ski-area “lifties” during their high school or college years and eventually became managers of various ski-area departments or even the mountains themselves.
This is very true of males who have long dominated the industry in leadership roles, but we rarely see it for women. They usually began as instructors or worked in day care or food services. Cindy Caira did the opposite.
She began working as a lift operator and now works for Okemo Mountain Resort as the director of food and beverage, one of several important profit centers for most ski resorts.
Born in Nahant, Massachusetts, Cindy Caira’s family moved to Mount Holly, Vermont, when she was 9.
“My mom lived in the mountains and my dad lived by the ocean so I had the best of both worlds, growing up on the ocean and in the mountains,” she said.
Caira first learned to ski at Okemo when she was 10 years old through the ski program at the Mount Holly Elementary School.
“The school programs are so important to get kids involved with an outdoor sport at a young age,” she observed, adding: “My skiing really took off when I worked at Killington and had lots of ski-instructor friends.”
After graduating from Saint Mary’s High School in Lynn, Massachusetts, in 1980, Caira went to Lyndon and Castleton state colleges. Marriage and children followed ,along with going back to school for a degree in business and starting a career in the hospitality industry.
Although she travelled a bit, Caira noted that she “always came back to the Green Mountains. I stayed here because of my love for the mountains. Vermont is a beautiful state for outdoor sports, and it’s a wonderful place to raise a family.”
Cindy Caira, Okemo food and beverage director
Q&A with Cindy Caira
Mountain Times (MT): How did you get to your job as food and beverage director for Okemo?
Cindy Caira (CC): I started in the ski industry as a lift operator while in college and waitressed at night. My passion grew for the food and beverage business as I entered into management positions and event planning.
I came to Okemo in 2010. It was a coming home for me. Over the past 10 years, I have developed my leadership skills while working my way through various outlets in management positions, including at Coleman Brook Tavern Epic Restaurant (now 43 North), the Round House, and Willie Dunns.
MT: What are your job duties and responsibilities?
CC: I oversee management staff and operations of five full-service restaurants and four quick-service restaurants, and I develop and grow talent.
MT: What’s a typical day like for you?
CC: My days can be hectic! I attend a lot of meetings, do a lot of email correspondence and solve problems as they arise.
MT: What do you like about your job? Best part? Rewards?
CC: What I like best about my job is the people -— my staff to be specific. I love watching talent grow. I really enjoy meeting and working with all of our international staff.
Seeing guests enjoying themselves is so rewarding. It’s nice to see people getting away and having fun.
MT: What are the challenges?
CC: Managing staff and juggling Covid restrictions and protocols offer some challenges. We have to be especially agile to adapt as circumstances change. And we are always on the lookout for qualified candidates to join our team.
MT: Any experiences or influences that were significant for you?
CC: It was the combination of all of my experiences that led me to where I am today.
The most significant change occurred when I started working for Vail Resorts. I have learned so much about the ski industry in the past three years.
Working for an enterprise with such diverse outlooks that really embraces technology has been incredibly beneficial to my growth as a leader.
MT: What are the changes and challenges you’ve seen in the hospitality field?
CC: During the pandemic, the world was turned upside down. So many people in the hospitality field pursued careers in different fields. The cost-of-living in ski towns and housing challenges have played a significant role in attracting new talent.
MT: How do you spend your time outside of work?
CC: I love spending time with my husband, my two daughters and two grandchildren. My hobbies are sewing and cooking. I spend lots of time at the yoga studio and love hiking, kayaking, snowshoeing and skiing.
MT: How would you describe the mountain and ski town lifestyle?
CC: It’s a blast!! Working for a resort allows you to ski or snowboard more often and enjoy an active, outdoor lifestyle.
MT: What advice would you give someone who wanted to work at a ski resort?
CC: Go for it! Have fun! Take advantage of the benefits and opportunities to grow. Work hard, play harder!
MT: Any advice or words of wisdom?
CC: Enjoy life, be happy and be kind.
