She learnt early that to get ahead in business in Spain she had to be fearlessly determined, a quality she has in spades thanks to her time in the Royal Air Force.

It was during her time in the British RAF that she learnt not to accept excuses or lies, as well as gaining an iron discipline.

“Being in the RAF was one of the happiest times in my life and where I had discipline instilled in me,” she tells the Olive Press. 

“As a result I don’t stand for any nonsense, but that also means people know where they stand with me, which is very important in business.”

It was still anything but easy for her to set up her insurance business on the costas three decades ago, when women were not taken seriously in business.

Jennifer Cunningham
Jennifer Cunningham

“I was a widow, surviving on a meagre widow’s pension and so the only way I could start up was to re-mortgage my home, borrow money and make it work,” she recalls, from her home in Javea, on the Costa Blanca.

“I had problems finding a bank who would support me and I remember the first time I presented my business plan to get a loan, the bank manager wouldn’t address me directly but kept looking towards the male friend I had brought with me.

“I had to point out that it was me who was borrowing the money, that I was the business owner and when they didn’t take me seriously, I walked out and went somewhere else.”

She eventually found a sympathetic bank manager, a man who has supported her ever since her first venture, and who she has stayed with as he moved across different banks.

She then began working with a giant American company, Liberty Insurance, designing special packages for the expat market and has built up a reputation as a hugely successful expat businesswoman.

“At the beginning they didn’t want to take me on and they felt sure that I would fail,” she reveals. “My style of selling was completely new to them, the culture here in Spain was so different.”

“As an entrepreneur I had to take risks and convince those who had the financial backing of huge institutions behind them to take a risk on me, but I proved myself and in the end, those very same people looked to me to lead strategy and even asked me to teach them how to do it.”

Today Jennifer Cunningham Insurance has seven offices in Spain (including one in the Canaries) and thousands of expat customers.

While an incredible success story – not just for a woman, but also as an expat – she however, is most proud of the fact that she leads a team of over 20 women across her offices.

“It isn’t a policy to only employ women, it just turns out that they are the ones that have thrived,” she explains.

“Applications are open to everyone and we have employed men and I try to keep a balance in the teams, but it’s the women that seem to be most successful in this business and the ones that stay on for years and years, while the men just don’t seem to keep up.”


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