Shot on location in the Bahamas / Creative Director + Photographer: Scharad Lightbourne/ Stylist: Hannah Sands/ Hair: Denise Francis/ MAU: Ge-Ah S Smith ZOOM Interview by Janette Brin Crediting God, consistent hard work, a multifaceted team, and

Shot on location in the Bahamas / Creative Director + Photographer: Scharad Lightbourne/ Stylist: Hannah Sands/ Hair: Denise Francis/ MAU: Ge-Ah S Smith

ZOOM Interview by Janette Brin

Crediting God, consistent hard work, a multifaceted team, and long-standing passengers for the continuous growth of Western Air Ltd., the largest privately owned airline in the Bahamas. Sherrexcia (Rexy) Rolle, gave us some great insights into how her hard work as Vice President of Operations and general counsel for her family owned business has blossomed into a Bahamian airline enterprise begun on Andros Island.  Daily flights from several hubs are scheduled between Nassau, Freeport, Congo Town, Bimini, and San Andros.  Charter flights throughout the greater Bahamas, Caribbean, Central and South America, are serviced and overseen by 140 employees.  The hard work and long hours have not taken away her bright spirit and energy; she manages to enjoy creating music and being involved in the social life of the islands. 

Captain Rex Rolle, Rexy’s father, serves as President & CEO and has a U.S. FAA and Bahamian certification as an airlines transport pilot, and as a certified flight instructor, certified instruments flight instructor, and certified multi-engine instructor with more than 30 years experience as a professional pilot, executive, and consultant.  Captain Rolle’s wife Shandrice Woodside-Rolle serves as Vice-President and COO of Western Air her degree in international business along with an entrepreneurial spirit keeps the company running smoothly.

Rexy Rolle: photographed by Scharad Lightbourne

POSH: How have the difficult times in the last few years with Covid-19 and major hurricane Dorian impacted your business outlook?

REXY:  We learned not to have all our eggs in one basket.  We learned to separate our organizational chart into the hubs and placing parts and inventories in different areas.  I don’t think that one could actually build for the level of hurricane that happened, but to see how our employees personally jumped into gear has made us more grateful for the wonderful team we have.

POSH:  How would you describe your home-life and your Bahamian-Caribbean upbringing?

REXY:  We had a very spirited upbringing that included grandparents, aunts, and uncles – literally a large family.  Even our non-family neighbors and friends would discipline us, teaching right and wrong ways to behave.  I was raised on Andros that is not populated by many people.  There was no one there homeless and if you were hungry there was always someone down the street that shared extra food.  I grew up understanding the importance of family and the importance of being disciplined and productive.

POSH:  I am from the Virgin Islands and can relate to your upbringing, but what is a must to do for a true Bahamas experience, since I have never been there?

REXY:  You should try the food experience first; conch salad, comforters, and Cracked Conch are just a small sampling and our Bahamas National beer.  I would suggest a visit to Exuma’s 365 islands with its most beautiful waters and cays.

POSH:  Congratulations on your recent interview with Forbes Magazine where you talked about being involved as vice-president of your family’s airline, an attorney for the company and a musician.  What drives your passion for a multi-level career?

REXY:  I believe that we are not one-dimensional; we have so many aspects to ourselves that need to be explored and expressed.   Since I was young, I feel and work best when I’m dealing with multiple things.  I offset my corporate life with some creative elements that I am interested in. Law is a very demanding and I balance that with music that allows me some creative outlet to balance myself

POSH:  Since working for your family business, what have you learned about yourself and what was that journey like?

Rexy Rolle: photographed by Scharad Lightbourne

REXY:  The journey began when I was 12 years old.  Now, we started our first flight in 2001 simply by providing a transportation solution, but it grew beyond our imagination.  We developed a consistent and aggressive approach to service.  I have to give my dad credit for that in terms of strategy.  Initially, we wanted to schedule maybe three flights a day.  The success we had with full flights prompted us to branch out to build a level of trust and commitment in us and so we were invited to other islands.  It was important as we grew to incorporate government compliance, corporate governance rules and some legal aspects into the business.  When I decided to enter law school I focused on what makes aviation run and how I could dovetail financing, leasing, mediation, and acquisitions along with all else, we were able to save thousands of dollars by not paying lawyer fees.

In the last five to six years we experienced significant growth and fine-tuning where we wanted to be.  As VP of Operations, it fell to me to talk to various departments to ensure that they are communicating to achieve the all important goals of being on time, efficient service and getting the customer’s bags to them.  A pilot for example, should not be concerned about ground handling.  We match the duty to each department so there is no overlapping of work.  I have learned to see the bigger picture of what our company is all about, and what I am all about as well.

POSH:  Did you choose to study law because of your interest in business, or have you always wanted to be a lawyer?

REXY:  I always wanted to be a lawyer since I was maybe seven or eight.  I told my parents I was going to be a lawyer and a pop star.  I ended up going to law school; I just didn’t know it would be so aviation based.  Western Air had started.  It just didn’t click with me until I found where I would be most useful.

POSH:  Can you tell us a bit about being a black woman in the world of aviation?

REXY:  Certainly at this point it has become much better, but in earlier days I was mistaken as being someone’s assistant, or a flight attendant.  The assumptions were automatic and not that there is anything wrong with being a flight attendant or assistant.  But I think your work must speak for itself. It took time for people to see how the operations continued to improve to really start to acknowledge.  I am a black woman and very vocal when I feel we are not treated fairly.  I don’t shy away from correcting something or someone.  We generally always come together about racial and gender issues and people do readjust to a good experience.

POSH:  Would you consider having your own law firm in the future?

REXY:  I would not right now because I’m committed to what we’re doing at Western Air, but because I recently had the pleasure of earning a legal education certificate under the Eugene Dupuch Law School in the Bahamas I may look at it in the future.  I am also a practicing member of the bar in California and Washington DC.  Many of our transactions with vendors and financial relationships are U.S. based.  We use external counsel for litigation and non-aviation concerns currently…Perhaps it may be great to have an all female law firm – it’s just an idea for now.  Right now I am more focused on Western Air receiving base certification from TSA to service the U.S.  We are really excited for this growth.

POSH:  When it comes to family businesses, what advice would you want to share with other Caribbean people with family owned businesses?  

Rexy Rolle: photographed by Scharad Lightbourne

REXY:  The core of any business is either being able to solve problems, or it is providing a product or service.  Beyond that you really don’t have much of a business if you are not in compliance with regulations pertaining to your industry and operating within the scope of.  After this you’ll be to spread your wings. Often people have a great idea, but may not know the return of the investment.  It is really important to be familiar with the breath of information on the country’s rules and regulations regardless of what kind of business you wish to start.  

POSH:  What would you say taught you the most about any failure within your career?

REXY: I would say overextending ourselves because we want to offer our customers options.  As an example, an island with 30 inhabitants may only need one flight a day instead of two.  We can’t place just one person on a flight.  If hotels and resorts can provide the people to fly with us, we will be there.

POSH:  You are obviously very close to your parents.  What is the greatest lesson you’ve learned from them?

REXY:  You’ve found my emotional spot talking about my parents.  My mother was 17 when she had me and my father was 22 – Marriage at ages 16 and 21.  I would say that we grew up together.  I would say they faced anything that was thrown at them, the stood on their faith first.  Secondly, they never gave up on their goals.  I learned those two key elements from them.  Today we have a myriad of options on how best to proceed with business and life: practical methods and theories on how to move forward.  But none of this was available to them in the early stages of the business.  They have learned that long-standing relationships are critical.  The relationship you build with bankers, financiers etc. creates loyalty that can last for many years into the future of your business.

POSH:  Are you a “daddy’s girl”? I noticed your father is Rex and you are known as Rexy.

REXY:  I certainly do consider myself a daddy’s girl.  He is awesome.  As to empowering women, we have to consider what men are willing to say.  My dad always told me to not let anyone push me down and that I am just as capable.  Instilling the values of hard work and getting a job done applies to my little brother and me equally.  I so value that.

POSH:  You have built an amazing personal brand for yourself in your music.  What was the key for you to develop this image, and what do you really want to be known for?

Rexy Rolle: photographed by Scharad Lightbourne

REXY:  The key for me was authenticity.  I like to mix variations of who we are as I have said before.  I like music, dance, and fashion too, not just seeing myself as a stuffy corporate lawyer.  I would like to be known for being fearless in pursuing other business ventures, various ideas and passion projects.  I want people to say I have lots going on and love to connect with people.  My music says Island Pop Easy, very chill.  Always reminds me of springtime.  I write all of my music and look forward to putting out more to infuse pop elements with continuing with Caribbean Island style and reggae influences.  I will be working on putting out more singles in the future.

POSH:  Tell us a little about your speaking engagements and mentoring young girls.

REXY:  I began a mentoring initiative with a friend of mine called Gallon Emission. Mentoring is incredibly rewarding and I still keep in touch with some of the girls and find it beneficial for both them and myself.  Ages 10 to 16 are a critical time for self-esteem, body image, and career planning and making smart choices.  I want to fee that I am really contributing to someone’s life and giving guidance.  We hope to do more events in the future when hurricane rebuilding and Covid is under control.

POSH: What do you do for fun?

REXY:  Well I love to eat and I love great conversations with family and friends and trying out new restaurants.  I enjoy sports and travel.  I enjoy a great spa day, meeting up with my friends and having fun!

POSH: Thank you so much for talking with POSH and we look forward to you being a part of the POSHgirl POWER Brunch. Is there anything else on your heart that you want to share with us?

REXY:  It is super important to be conscious of who you are as a person, the things that you like and move you; that helps to find your purpose.  Thank you so much.  It has been a pleasure speaking with you.

Behind the Scenes


Caribbean POSH is a platform dedicated to celebrating and empowering Caribbean women. Our mission is to highlight the achievements, talents, and resilience of Caribbean women, while providing a supportive community that encourages personal growth and success. Join us in creating a brighter future for all.


Caribbean POSH is a platform dedicated to celebrating and empowering Caribbean women. Our mission is to highlight the achievements, talents, and resilience of Caribbean women, while providing a supportive community that encourages personal growth and success. Join us in creating a brighter future for all.

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