Man after man has served as commodore of the Royal Hamilton Amateur Dinghy Club since it was formed in 1882. This year, Elspeth Weisberg broke that tradition.

It was not her intention when she joined the private Pomander Road club but, having frequently been the only female in the boardroom, it was not an unusual spot for her to be in.

“I didn’t start out to be a pioneer or anything, but [my parents] set expectations that failure, or achieving less than you were capable of, was clearly an undesirable outcome,” said the former reinsurance broker who is now director of business development at Fergus Reinsurance.

“I was only the sixth woman to get a ticket to transact business on the floor of Lloyd’s.

“I didn’t set out to do it. I guess I was brought up with enlightened parents who never threw up obstacles and, certainly growing up here, no one ever told me there were things I couldn’t do.”

Her non-sailing parents, Tom and Sheila Gray, signed her up with Camp Juniper, a summer programme on Agar’s Island; lessons at the Royal Bermuda Yacht Club helped her progress.

For her working parents it was a way to “get rid of me for the whole summer”, but she saw it as something more.

“I always loved it,” Ms Weisberg said. She sailed throughout her time at the University of Edinburgh where, on a Bermuda Government scholarship, she studied German and international law which “qualifies you to do basically nothing”.

During summer holidays, she worked at the airport with British Airways. Her job began at 3pm in anticipation of the arrival of a 4pm flight from London that, depending on the day of the week, then departed for the Bahamas, Jamaica or Panama.

“We had to meet the arriving flight from London and make sure everybody got their bags.

“In those days, there were no computers. We did all the check-in by hand, we hand-wrote all the luggage tags. We did all that in preparation for the flight coming back from the south — about 9.30 at night — which left for London at about 10.30 or 11.

“It was invariably late and we didn’t get off work until midnight or later. After 11 at night, you were on overtime and if it went beyond 3am you were on double time because then you’d worked a double shift. So some months, with lots of delayed flights, I was bringing home a paycheque from my summer job which was more than my mother earned as a teacher.”

With nothing planned, she was thrilled when British Airways invited her to join its management training programme.

“I had such a fantastic summer job for the whole three years I was in university,” Ms Weisberg said.

“I graduated from university in 1981, which was the depths of the aviation industry recession — one of the many — and they cancelled their graduate intake. And they didn’t let us know until the end of July that they were cancelling it and there was going to be no graduate intake that September.”

With no other prospects, she returned to her boyfriend in the UK. Her father agreed to fund her — but only for about six weeks.

Although she “knew nothing about insurance” she was fortunate to snag a job with an insurance broker.

“I learnt everything I could and I went to college in the evenings to get my ACII, Associateship of the Chartered Insurance Institute.”

She was offered a full-time position at the end of her probationary period but turned it down.

“I used to wash dishes in an Italian restaurant on Friday and Saturday nights just to make enough money to live on for the week,” she said.

“I think I was earning something like £1,600 a year. I came home and got a job at Walton Insurance, which was Phillips Petroleum’s captive, and I was earning $16,000 a year. And I didn’t have to pay tax. And I could live at home, so I didn’t have to pay rent.”

A year in, the company went into runoff. Although invited to stay on, a “very kind underwriter” advised that she return to London and passed her résumé on to his contacts there.

“They wanted to train Bermudians in the industry. We still do. I got letters from two Lloyd’s brokers asking me would I like to interview with a position with them.

“It was the best ten years of education you could get. I went to London right after Hurricane Alicia, which was a major loss and caused a lot of changes in the market.

“I was there for Piper Alpha, which was then the largest man-made loss; a huge loss in the energy market.

“I left right after Hurricane Andrew, the catalyst for the formation of the property cat market in Bermuda. If you had to look at a ten-year span to spend in London — and this is just luck and timing — you couldn’t have picked a better ten years.”

Throughout it all, she continued to sail. Also an avid tennis player, on returning home, she applied for membership at Coral Beach & Tennis Club and was put on a waiting list; at the Royal Bermuda Yacht Club, she was unimpressed by the lack of involvement women were allowed in its running. She joined RHADC delighted by its tennis courts and the opportunity to sail.

About ten years ago, she joined the Committee of Management at RHADC. Impressed by her performance as president of the Bermuda Sailing Association, members of the club’s nominations committee suggested her for the top job.

“I served first as a rear commodore — it’s a two-year rotation. Two years as vice-commodore and then, subject to all going well, you get elevated to the top spot for two years.

“You then become the past commodore and sit on the nominations committee for three years. Basically, it’s a nine-year commitment.”

As commodore, it falls to her to “advance the welfare at the club by every means”. On her wish list is a fleet of boats that would give more members access to the water and allow more international events to be held here.

Under her leadership the rules were recently changed to make the club more inclusive.

“We had 90 kids in our summer programme this summer. A lot of that is because people didn’t go away, but the Endeavour Programme, which was started by the America’s Cup Event Authority, was a fantastic feeder for sailors because it gave access to sailing to kids from the public schools and to people who didn’t have a family background in sailing, so had never been brought up with the expectation that they would go sailing.

“We want to appeal to younger members, we want to get away from the sort of stodgy misogynist image that a lot of yacht clubs have. So [our rules now address] equal treatment of members and employees without discrimination on the basis of race, colour, religion, gender, marital status, disability, age, sexual orientation, gender identity or national origin.”

Ms Weisberg also has her eye on a personal accomplishment. In her early forties, a friend who had recently qualified as an international umpire inspired her to do the same before her 50th birthday.

“I didn’t achieve it, but I am an international judge appointed by World Sailing; [someone] who sits in a courtroom and adjudicates the rules.

“I am also a national umpire, I’m qualified in Bermuda, but I’ve not done my international umpire qualification yet because I don’t have time,” she said.