Drive, ambition, enthusiasm, passion: the secrets to success according to Bermuda’s rising stars. These successful twenty-somethings are on the fast track to becoming industry leaders, proving that there is no limit to achievement at any age.


Stephen Outerbridge

Bermuda Commercial Bank

Stephen Outerbridge credits “staying focused, having patience and discipline” as major factors to success. These are the same qualities Outerbridge uses when he’s hard at work on the cricket field. As a member of Bermuda’s 2007 World Cup Cricket Team and former vice captain of the Bermuda National Cricket Team, Outerbridge is no stranger to the dynamics of teamwork, but he’s also working toward a personal goal as well: “heading an investment firm with at least $100 million worth of assets under management.”

In August 2009, he joined the Bermuda Commercial Bank with “little to no banking experience.” After just two years, he has worked as a banking service administrator and is currently training in dealer and cash management, a position where he will be responsible for the bank’s assets, liabilities and foreign-exchange positions. After how far he’s come, Outerbridge can’t forget about his former team, thanking the Bermuda Cricket Board “for affording me the opportunity of gaining an education.”

Currently working toward his Series 7 designation and a degree in banking and finance, Outerbridge advises those wishing to follow in his footsteps to “be prepared for a steep learning curve with the ever-evolving business.” It’s that ever-evolving business that keeps him on his toes. As he says, “There’s never a dull moment in the dealing room!


Shellé Hendrickson

Allied World Assurance

“The insurance industry is built on relationships, and the more contacts you are able to secure, the more successful you’ll be at winning business,” says Shellé Hendrickson, underwriter for healthcare at Allied World Assurance. Building relationships is what Shellé is good at. Her ability to establish a rapport with anyone she meets has made her a huge asset to her team, earning her two promotions since she started at the company in January 2005. “You can easily find yourself following up with a broker about their dog’s first visit to the groomer or asking for vacation ideas.”

Although Shellé is now at the top of her game, she wasn’t always so confident. “Public speaking was by far the biggest obstacle I had to face.  There was no avoiding it.” With client meetings, meetings with brokers, conferences and various social functions, Shellé had no choice but to face her fear for the sake of doing a good job. Now six years later, Shellé is a natural. “Pretty much any time I’m not working at my desk, I’m speaking publicly.”

Shellé’s advice for those starting out in the industry? “Be prepared for every meeting, no matter if you are going to a department meeting, committee meeting or client meeting. Go equipped to speak intelligently as you never know who in that room will have to make a recommendation for you.”


Edison Jecoa Tucker

Fairmont Hamilton Princess

“Bermuda is a very unique product, and I intend to sell it at every opportunity I get,” says 25-year-old Edison Jecoa Tucker, currently enrolled in the prestigious leadership development program at Fairmont Hamilton Princess. For the next 12 to 18 months, Tucker will be exposed to numerous opportunities within the hotel and trained under various departments, setting him up to become general manager within 10 years.

“I have always dreamed of managing a hotel, and I am extremely grateful that the Fairmont family has set me on track to one day seeing my dream turn into a reality,” he says.

And it doesn’t stop there. Tucker hopes to one day become Minister of Tourism, making a valid point that after years of experience in a top position in the hospitality industry, he will be perfectly qualified to lead Bermuda’s tourism industry into the future. “There is nothing more exhilarating than being able to promote and represent your country, and that is what I enjoy and do best,” he says. “We are one of the smallest countries in the world with one of the biggest personalities. I love being an ambassador for my country.” It’s a role he believes more young people can take on. For those wanting to follow in his footsteps, Tucker says, “Start by doing what’s necessary, then do what’s possible, and suddenly you are doing the impossible.”


Sergio Lottimore

Amlin Bermuda

“My start in the industry was the by-product of years of preparation and the perfect opportunity,” says Sergio Lottimore, catastrophe modeling analyst at Amlin Bermuda. “I posted my résumé on the Bermuda Foundation for Insurance Studies (BFIS) website, and by chance the recruiter stumbled upon it.” Shortly after, Lottimore was hired as an underwriting assistant, a position he mastered before being promoted to his current position this year.

Lottimore advises those interested in insurance that the secret to success is “to be willing to positively differentiate themselves from the crowd,” learning all they can and putting their knowledge to use. “Developing these capabilities will enable them to take advantage of any opportunity that comes their way,” he says. In fact, Lottimore says he continues to develop his skills in anticipation of future opportunities. “I would like to become a leading executive of a reinsurance company. I enjoy the big-picture aspect of executive managerial positions, and the benefits don’t hurt, either,” says Lottimore. “If I continue with my existing drive and commitment to learning, I am confident that I can achieve this goal.”


Devin Page

Graduate student

Devin Page is dedicated to advancing in his field. At press time, Page was moving to Atlanta to enroll in Georgia Tech as a graduate student, working toward his master’s degree in international affairs. Bowring Marsh, where Page has worked for two years first as a technical assistant and then as an associate broker, hopes to see him return after graduation, although nothing is set in stone quite yet.

Indeed, Page believes one should never stop learning. “Knowledge and credibility are pretty much all you have going for you, so establishing that as quickly as possible and maintaining it is always crucial,” explains Page.

For those wanting to follow in his so-far-successful footsteps, Page says, “Be humble and work hard. Forget about thinking you deserve any special treatment, and don’t just do your job, take time to learn and understand as much as you can about it as well.”


Dakeisha Ratteray

Bermuda CableVision

Dakeisha Ratteray embraces a challenge. Her objective? To acquire the skills and knowledge it takes to hold a managerial position at Bermuda CableVision. Currently the lead customer sales representative, Ratteray started working for CableVision at 15 as “the bag girl,” responsible for handing customers their cable boxes and remotes over the counter. “In my opinion, I had the best job!”

It was her enthusiasm and dedication that got her noticed. She says, “Work hard, as no good deed or extra effort goes unnoticed.” It’s the extra effort Ratteray puts forth that sets her apart from the rest.

Ratteray is appreciative of “the entire Bermuda CableVision family for all their support” and hopes to grow within the company. Although she says she hasn’t faced any major obstacles on her journey so far, she’s sure a day will come when she will. However, unlike most other 22-year-olds, Ratteray doesn’t feel threatened; instead, she’s prepared to face whatever life hands her.


James Botelho

Validus Re

James Botelho
believes the best is yet to come. Botelho is the assistant vice president and pricing actuary at Validus Re, a position he’s spent years working to attain. “I would caution anyone thinking of becoming an actuary that it usually takes the better part of a decade to reach the finish line.” To Botelho, the hard work is worth it; his position demands respect within the workforce, and he enjoys the opportunity to have a lasting impact on the direction of his company.

Botelho credits his parents for encouraging him to set high goals for himself and supporting him through the many years of studying and exams. He says actuarial science is “one of the toughest professional qualifications in existence” and urges those wishing to follow in his direction not to get discouraged when things get difficult. He indicates that the biggest obstacle he has had to overcome was “staying motivated and positive after failing an actuarial exam.”

After years of hard work, it’s no surprise that Botelho isn’t stopping any time soon. He hopes to gain more experience and one day become a chief actuary of a Bermuda reinsurance company. For now, Botelho is happy reaping the rewards of his hard work. “There are very few global reinsurance centres where I can leave work at five fifteen and be out on the water sailing by five thirty!”


Raquel Pitcher

Ariel RE

Raquel Pitcher’s start in the insurance industry came after a friend encouraged her to apply to university, saying she was “too smart to not go to college.” To Raquel’s surprise, not long afterward she was accepted by the University of Hartford and began working toward her degree.

“The biggest obstacle for me was learning to let go,” she says. But facing that fear and leaving her past position as a sales clerk allowed Pitcher the opportunity to expand her horizons and earn a degree in business administration in 2007. Pitcher now works as a risk analyst at Ariel Re.

For someone who almost didn’t go to university, the enjoyment of learning has had a lasting effect. “I love the fact that there is an endless amount of learning in this industry,” explains Pitcher. “I have learned so much about so many things—a lot of which I think most people would never guess you could learn in this industry.” Some of those things include having to understand the formation of hurricanes and the ins and outs of construction and engineering projects. Pitcher says the secret to being successful in her line of work is to stay current. “There is always something new coming, be it via e-mail or seminar or white paper,” she says. “Something is always changing.”


Azeem Pitcher


As the lead technical analyst at HSBC, it’s Azeem Pitcher’s job to stay up-to-date with world affairs in order to predict price movements in Bermuda’s local and international markets. “The industry is constantly changing, and we have to be able to change with the times and adjust to a changing environment.” For Pitcher, that changing environment isn’t just our tiny island, but the world economy as well. “The most exciting thing for me in my career is that I find myself working with people from Asia, North America, Europe and Cayman on a daily basis.” Pitcher explains these are the benefits of working for HSBC, which he describes as “a great environment to grow professionally, technically and personally.”

For Pitcher, it was the benefits of networking that landed him his job at HSBC. “A colleague brought an HSBC employment advertisement to my attention during a networking conversation. As soon as I read the job description for a lead technical analyst at HSBC, I knew I’d found the perfect fit.” He encourages other young people to do the same: “Understand the importance of networking, meeting people in your industry and leaving a positive impression.” Never underestimating your chance at success even on a small island helps, too, according to Pitcher. “Though physically small, the opportunities are great.”


Jonathan Allen

ACE Bermuda

For Jonathan Allen, title underwriter at ACE Bermuda, success isn’t always derived from perfect grades. “Good grades are great, but a lot of students have good grades. They should have extracurricular activities behind their names as well. They should have something other than academics behind them which helps to differentiate them from other students.” In addition, Allen says, “Making a good impression when networking and sustaining that impression is important. That good impression can boost you to the short list when it comes to getting a job or scholarship.”

After all, Allen would know. After a chance encounter with Allen in his second year at Bermuda College, Lisa Bean, an excess casualty underwriter at ACE Bermuda, was impressed by his ambition. She arranged meetings between Allen and experienced underwriters at ACE and other companies. It was those meetings that led to internship opportunities for Allen and ultimately to scoring a full-time job with ACE in 2005.

In his current position, Allen fears and enjoys the uncertainty of the insurance industry at the same time. “It definitely keeps me on my toes,” he says. “I can do all the underwriting checks and due diligence in the world with the information I have on a particular account, but I still cannot predict the future.”


Terée Tucker

Bermuda Gas and PureNERGY Renewables

“In order to be successful, you don’t have to follow a predicted path when you can chart your own,” says Terée Tucker, human resource manager at Bermuda Gas and PureNERGY Renewables.

For Tucker, following her own path was what led her into human resources, an area of business she’d never thought about working in until she found herself in an unhappy position at a marketing firm. Her search for a new job led her to the HR department at BF&M Insurance. “I received a call offering me a position as an intern in HR. I started the following week and never looked back.”

Fast-forward to 2011 and Tucker’s love of the business has only grown. “I love this line of work!” she explains. “HR touches the future, it helps to promote innovation and some might say it brings an element of humanity to a business.” Even more intriguing, Tucker says, are the benefits of working in her island home. “While I value international experience and would love to have the opportunity to work overseas, I find working in Bermuda to be a rewarding experience,” she explains. “There is something special about working at home and being able to see how your efforts support your own community’s growth.”


Ebony Fray

Butterfield Bank

Ebony Fray is a people person. In her position as a learning-development specialist at Butterfield Bank, Fray enjoys helping her co-workers grow professionally. “I love the feeling of knowing that in some way, and with immediate effect, I am helping a colleague when they walk through the doors of our training facility.”

Having graduated from St. Mary’s University in 2008 with a bachelor’s degree in commerce, Fray was recruited by Butterfield Bank as part of the management-training program, an 18-month course during which she was trained in a variety of positions and worked to develop her leadership skills. Fray now is responsible for training her co-workers using her knowledge of banking as well as her knack for motivation. “Do more than what is required,” she tells her colleagues—something she says should be used universally.

Fray is quick to encourage others to follow in her footsteps, especially taking opportunities to travel abroad for work. Although she loves Bermuda and is appreciative of the opportunities she has received here, she says that “professional overseas exposure will not only enrich your résumé, but also your life.” She experienced this herself after living and working in the Cayman Islands. “After having spent 15 months in Cayman, I am excited about everything. I am really looking forward to establishing a footing within Butterfield and progressing up the ladder.”