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Meet a Reinsurance Executive - Sylvia Oliveira

Sylvia Oliveira is CEO of Wilton Re Bermuda, where she works with clients to enhance their value through the reinsurance and acquisition of inforce blocks of life insurance products. Sylvia is also CRO for the Wilton Re Group, where she has implemented and oversees their ERM framework.

Sylvia has served on the Board of BILTIR (Bermuda International Life Insurers and Reinsurers) since inception, where she has led several committees and working groups. She actively advocates for the Bermuda’s life sector on regulatory and tax issues. Sylvia is also a director of ABIC (Association of Bermuda International Companies), where she represents the life sector in government matters.

Sylvia has over 25 years of experience in the insurance industry, including seven years at John Hancock in Boston, nine years at Chubb Tempest Life Re and four years at Annuity & Life Re in Bermuda, in a broad range of life insurance and reinsurance functions and product lines. She has been listed among the Influential Women in Re/insurance by Intelligent Insurer magazine and the Influential Women of Bermuda by Bermuda: Re+ILS magazine. She co-authored “Actuarial Aspects of ERM for Insurance Companies” as part of the Enterprise and Financial Risk Committee of the International Actuarial Association.

She is a Fellow of the Society of Actuaries , a Chartered Financial Analyst and hold Bachelors and Masters degrees in Mathematics from Boston University.

Tell us about your life outside of work?

I am the proud mother of Skye and Jack, who are both keen sailors and musicians. I volunteer my time serving on the boards of Open Airways, a local asthma education charity and the Menuhin Foundation, which provides string lessons to Bermuda’s youth. I enjoy playing violin with the Menuhin adult orchestra and the Bermuda Philharmonic, and I am also a long-standing member of the Chaîne des Rôtisseurs, an international association of gastronomy.

I find Bermuda’s high concentration of forward-thinking intellectuals to be inspiring and motivating, and I am grateful my career brought me to this beautiful island 20 years ago.

How can we ensure more women reach senior levels in the reinsurance industry? This is a question I think about often. Why is it that women earn the majority of undergrad and masters degrees (60%) and make up half of the US workforce, yet women only hold 20% of the Fortune 500 seats and only 6% are CEOs (more recent stats are showing a decline to 4%). Sadly, the proportion drops to 0.4% for women of color. Studies have long proven that increased gender diversity correlates positively with increased profits. What is going wrong? Here are couple of actions I am taking: First, there is a commonality among the female Fortune 500 CEOs: Nearly all of them majored in hard sciences. In order to achieve diversity and equality in the workplace, more young women should be encouraged to study and work in technical fields. I have personally committed to support the development of a STEM center at our local girls high school, which I hope will see more graduates majoring in hard sciences. Second is the confidence factor. I personally know several successful capable women who have been reluctant to put their names forward for leadership roles. Frequent presentations and speaking engagements are expected duties for these roles. If we can help build confidence in public speaking, I think more women would be comfortable stepping into C-Suite leadership roles. Currently I am working with an organization with a goal of coaching women on public speaking and working with conference organizers to include more women speakers. Women would benefit from the speaking experience, and frankly, we are tired of seeing ‘manels’ (man-panel). As a mother, what tips do you have for balancing family commitments with career/clients? The balancing act is a constant struggle for me. Happy to share some tips that have worked for me, knowing these will not be helpful for everyone. My number one tip is to accept or hire help. This became more and more critical as my children aged. After-school transportation to and from home and/or activities is challenging. I hired a fantastic helper to help with driving, childcare and cleaning every afternoon. The helper would stay with the children in the evening until one of us came home. The key was to eliminate the pressure of having be home by 5:00 pm each day. I also focus on practicing mindfulness and ’being present’ whenever I am with the kids. When I am with them, I try to put down my phone and emails so I can be 100% present.

What are your favorite places in Bermuda for entertaining clients ?

My favorite spots for having a meal are Bolero and Coral Beach Club. We enjoy holding events at Hamilton Princess and at the Yacht Club.


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