The Search For Something Magical

Jessi Chai, Allard ‘08
Director of Communications and Project Management Office - Marriott International Asia

Jessi Chai’s hospitality career has taken her to the Swiss Alps, the glitz and glamour of Dubai, the mountains of northern Oman, and cast away on an island in the middle of the Indian Ocean. Her most recent move has taken her to Hong Kong where she is responsible for Communications and Project Management for Greater China at Marriott International.
Following her graduation from Brentwood in 2008, Jessi attained a Bachelor of Arts at Simon Fraser University with a Major in English Literature and a Minor in Early Childhood Education. Her desire to nurture preschool children following her studies quickly took a turn, as she made her first step into the world of luxury hotels, falling in love with the dynamic inflow of diverse people at the Fairmont Pacific Rim in Vancouver, BC. Following this newly cultivated passion, Jessi moved to Switzerland to complete her MBA in International Hospitality & Service Industry Management from Glion Institute of Higher Education in 2014.
During her studies, she received an offer from Movenpick Hotels & Resorts in the United Arab Emirates, where she held various roles over two years. From there, she took on her first managerial role as Assistant Marketing and Communications Manager at Anantara Resorts & Spa based in Oman. After two years in Oman (which she intimates should definitely be a country on your go-to travel list) the Maldives came knocking and once again she was on a jet plane to yet another remote location, this time as Director of Marketing & Communications for the W Hotels & Resorts.
Always open to new adventures, Jessi continues to follow her career around the world, exploring diverse cultures, languages and foods while waltzing away at her computer and teaching the occasional yoga class to friends, family, and aspiring yogis.
We sat down (virtually) with Jessi in Hong Kong, to talk about her time at Brentwood, her career, her aspirations, and what she has learned along the way in her globe-trotting career. Here are some excerpts from our discussion.
How did this journey into hospitality and globe-trotting start for you?
I was a fresh graduate, finish my degree from SFU, and wondering what I was going to do with this fresh piece of paper. My mum said, “You love people so why don't you try working for hotels?” And I thought it was a great idea! I was so naive at the time that I didn't even know that it was possible to have a career in hospitality and marketing. So, I applied for a couple of jobs and thought this was exciting. I loved the job title. I just applied for everything, not knowing anything. But I didn’t get any callbacks ... then I thought, Oh my goodness what is wrong? I desperately wanted a job so I applied for housekeeping, and got an interview. The lady that I met with, I think she was the Director of Housekeeping at the time, looked at me and said I really admire your passion but I don’t think housekeeping is for you but let’s try around the corner in the little cafe and see if food and beverage need somebody. My eyes lit up again. I got my second interview a few days later. I did not know the difference between a cappuccino and an Americano. I mean, I was a lifeguard getting myself through university. I didn’t know a thing about coffee. But they must have seen something in me because I got the job.
It was the best place to start because you see all the regulars, the bosses, the entrepreneurs, who come in for their soy something fancy. You start to get to know their names and see them all the time. After six months of working there, I talked to my boss. I had a great support team, super encouraging in so many ways. So after six months, I said to my boss, “I love this job and I’m heartbroken because I would now love to go back to school and study hospitality before I don’t want to study anymore.” He suggested that I go to Switzerland. So I looked into it, and a couple of months later I said to him, “Look I’m serious about this now and I will have to quit. And I’m going to go to school in Switzerland.” They supported me the whole way. They even paid for my hotel there for the first five days! They did not have to do any of that. That’s really how it all started. Fairmont and I taking on this challenge to leave Vancouver and move to Switzerland. Had I not done that, I probably would have just stayed in Vancouver.
So what precipitated the move into Marketing and Communications?
After completing my MBA from the Glion Institute in 2014, I said yes to a management trainee program with Mövenpick Hotels & Resorts in Dubai. I went through a one-year rotation of all the departments and found the Marketing and Communications most appealing. I had great mentors who showed me the ropes and encouraged my social media ideas.
Having travelled to over 40 countries, which ones stand out to you?
Oman. Absolutely the most underrated place ever! Beautiful people, amazing culture, amazing nature - I did not want to leave Oman. It was so beautiful. Being in Oman for two years was not only the best for me but it was also the role that pushed me up in my career. I think I learned the most in Oman and at this hotel specifically. It was so beautiful, such an iconic hotel. If you ever get a chance to watch BBC’s Amazing Hotels: Beyond the Lobby, in Season 2 along with the Marina Bay Sand they look into the lives of all the hotel guests. They really do tell the story of not just the beautiful resort but touch on the people there, which is amazing. When I first got to the resort, one of the first meetings I had was with BBC from the UK who were seeing if we would qualify for the show. It was an hour-long episode and they came to film for twenty one days. At that moment I thought, I have no idea what I am doing. I've never done media to this extreme before. Yet here I am being thrown in the deep end. I either sink or I keep going. Some of it you just pick up along the way and I’ve just been really lucky. Again I always come back to the people, because it was this amazing film crew and amazing team. Oman shaped me, in so many ways. If you haven’t gone, you need to go!
So, for Brentwood specifically, what kind of student were you?
Oh, that’s a good question. I was the very typical Asian, shy, sat in the front row, didn’t talk to anybody, only had Asian friends, very shy. I mean the only thing about me that was not stereotypical was that I sucked at math and I didn’t play the piano. I did not take Math 12. I was very much into Outdoor Pursuits, the sailing club, the running club, anything that brought me outside.
My favourite class would have to be pottery with Mrs Elmes. Gosh, I loved her. I was more into the art side and sucked at sciences. I was a terrible student but I was quiet and always sat in the front row and always did my homework. Nothing rebellious. I didn’t hit that at Brentwood. I wish I would have been a little bit more outgoing. Because I was just super shy. I loved cookie break and breakfast and meal times because all the cafeteria ladies were so awesome. I just remember them being the fun time at school. They just weren’t afraid to be goofy and silly. I loved that energy.
What was special about the School for you?
Mermaid forever! Gwynneth/Allard 2008. So, we were the last set of girls to live in Gwynneth and then the next year, my Grade 11 year, we were the first girls to live in Allard House. My Houseparents were Lorraine Blake, the dance teacher, and Jill Fougner. And then in came the Carr Family, Mr and Mrs Carr. And I think my best friends are from Brentwood. It doesn’t matter how far I travel around the world, it's the core of the relationships that I have and still keep today. It stays true to my heart. I send them postcards from wherever I am. And they love it! Because at least I get to say hello from around the world.
You know what has also stuck with me? The number one inspections. I think, when you're younger you don’t appreciate it, but growing up and having to live on your own you realize that yes, it’s great to clean up and colour coordinate your clothes and stuff. I think that really stuck with me. I changed it to Sunday I think, but it was consistent, that clean-up once per week. I think that’s why Brentwood was so great because you have your arts on some days and you have your sports, you have that kind of structure, it helped me develop me. You don’t appreciate it at the time. Definitely not. But every morning you wake up, and it’s like that dewy foggy morning and breakfast. It’s just it was so amazing those three years at Brentwood. The best of friends, and art, and even the food.
Do you think there was anything in that experience that informed where you ended up?
I was definitely slow to find my own two feet in exactly what I was to become in life. No, I don’t think that a moment ever happened to me. I was not only shy but I thought I wanted to be a teacher. I didn't know what was out there and what was being offered. I was just trying to finish school. A lot of Brentwood kids are very intelligent; they go in having their end goal in mind. I didn’t have that. I knew I wanted to do something important but I didn’t figure it out until it started to happen. And now, having joined hospitality, and really being able to share my story and influence other people and younger girls and boys and tell them to go for it - I think is so great.
Wait, I’d never thought about this before, but you know what, it was the art, the afternoon classes, that did shape me. The art classes, the photography classes, all the creative side and also running for me was something else I also started with Tate Rose’s dad, Rob. And then there was a cafeteria lady who would always run in the back with me. I think her name was Lorraine? She drove a little Volkswagen Beetle, like the one in Scooby Doo! Amazing lady. She, and that I even remember this is so strange, she always smelt lovely and it was Coco Chanel, her perfume. She always ran with me at the back of the pack.
Now thinking back, it goes back again to all the stories you hear as a kid, that life is not a race. You can be the last one. I still run to this day. If I don’t run I don’t feel alive. So, I wake up every morning before work and I run for 5km. Now that I’m thinking about it, it does all add up. The arts and running, it does actually all fit, the little pieces all the way.
What have you learned most through your travels? About yourself?
I find it fascinating how different cultures behave, face conflict, and work together. I have learned that nothing is constant and that happiness comes from within. I used to be on the search for something magical, then, in the Maldives confronted with the Robinson Crusoe lifestyle, I realized that happiness comes from within. It’s a state of mind that can be influenced easily and we can choose to appreciate all the small things.
So why the move to Hong Kong?
Ideally the location and being closer to Taiwan where I was born and being able to see my family more often. Having traveled to 40+ countries in the past seven years it’s surely time to place family close.
What is one of your biggest travel hacks?
Oh my goodness, okay. I travel a lot but I am the worst traveller. I’ve gone to the airport and I’ve forgotten my luggage! I’ve gone to the airport and not had a Visa! I’ve gone to the airport and sat at Starbucks and missed my flight! I literally send my tickets to my friends so they can set an alarm and Whatsapp me to make sure I am on my, at the airport, or checking in. It’s different checkpoints of Jessi getting on her flight. It’s a constant joke. But my advice would be to always have a pen so you can fill out forms. That’s the simplest thing I can say. And that one I have not screwed up yet.
What drives you? At work? Personally?
It may sound crazy but I just love my job! I love the planning of events, influencer visits, the excitement of photoshoots and videoshoots followed by the anticipation of the final work. I guess just being able to wake up in the morning with a smile and try to make a difference in the world. My role model is also my mother.
Anything you'd like readers to take away from your experiences?
Say yes to yourself and all the possibilities that lie ahead. Dream big, be kind and be bold!
It’s really all about the people and you always meet them again in some way. So as cliche as it is, it’s so true: treat each other the way you want to be treated. A simple good morning with genuine excitement or thank you that was really nice. Or sometimes just simple cookies. I think it goes beyond hospitality in such a strong way. Now, we can keep in touch with Zoom and social media and everything, and we feel connected. Even things like writing a person a little How are you? How actually are you? You came into my mind, I thought about you. The little things matter.

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