Leaders’ Showcase: Sylvia Oliveira
The Wilton Re CEO has been involved with the Bermuda long term re/insurance sector since its very beginnings.
Sylvia Oliveira has been a leading light of the Bermuda long-term re/insurance industry since it began a quarter century ago.
As a former chair of BILTIR and a founder of a newly formed Bermuda actuarial association, she has always been committed to strengthening the re/insurance sector.
Give us a snapshot of your career to date.
My career started out at John Hancock in Boston, where I was hired as an actuarial analyst fresh out of college. After obtaining my FSA, I was recruited to work at a life reinsurer start-up in Bermuda. In my 25 years in Bermuda, I’ve worked in a wide range of functions (ALM, ERM, pricing, valuation) and with the spectrum of US insurance products at ACE Tempest (now Chubb) and Wilton Re. It’s been an honour to serve the industry as a director and past-chair of BILTIR, where I continue to actively advocate for the Bermuda life sector. Under my directorship, BILTIR developed a framework to foster local talent through a BILTIR scholarship, a summer internship programme, career-based Lunch & Learns, and volunteer maths tutoring. I also served as a member of the Bermuda Economic Advisory Committee to support the Minister of Finance on post-COVID economic recovering planning.
What attracted you to re/insurance?
My mother, also a mathematician, encouraged me to explore the actuarial profession while at university. It was a perfect fit for me - I even founded an actuarial club at my school. After working for seven years at John Hancock in Boston, my first Bermuda job was at a life start-up called Annuity and Life Re. The breadth and variety of work was a large contrast from my previous experience, as well as the start-up vs. large company culture. In reinsurance, each deal is bespoke. I was drawn in by the complexity of each deal and the broad exposure to many types of products and risks.
Life insurance protects families from hardship, and the Bermuda life market provides diversification of risks and the reduction of costs to policyholders, helping to maintain of a robust industry that policyholders can count on for decades to come. I’m grateful to be a part of the reinsurance industry, which has global impacts in filling protection gaps and makes log-term stable contributions to world economies.
Who inspired you or acted as a mentor?
I've been fortunate to have several mentors throughout my career who have provided guidance, support, and inspiration.
I’ve already mentioned my mother, who inspired to embark on the actuarial career path. Years of actuarial exams and insurance roles provided me with the essential technical training, but I received no formal training on the managerial skills needed to excel in as a leader. I had to rely on self-study and a few strong mentors along the way, including the late Bob Reale, who supported me along my career until his recent passing. Paul Medini from Chubb, and Chris Stroup and Dmitri Ponomarev from Wilton Re have also been invaluable mentors to me, providing me with guiding examples of authenticity, decisiveness, accountability, compassion, and resilience.
Greatest challenges during your career?
From a work perspective, the challenges are constant - market volatility, regulatory changes, and innovation all create new and interesting dynamics. From a personal perspective, my greatest challenge by far was balancing work with raising a young family. Looking back, I’m not sure how I made it through those years - lots of late nights and cherished support from friends and family. Post-Covid, increased acceptance of working from home helps ease some strain
Has there been progress in diversity and inclusion?
There have been great strides in D&I, but more can be done. Among my Bermuda life reinsurance peers, I am pleased to see several women in leadership roles. Among our BILTIR board, for example, half of the directors (six out of 12) are female. Overall, however, male-to-female ratios in executive positions is nowhere near equitable proportions. Women earn the majority of undergrad and graduate degrees (60%) and make up half of the US workforce, but sadly women CEOs only run 10.4% of Fortune 500 companies. Studies have long proven that increased gender diversity correlates positively with increased profits, so it would make sense for companies to focus on improving this gender imbalance.
Is the sector attuned to diversity and inclusion?
The sector continues to recognise the importance of diversity and inclusion, but more work can be done to fully integrate these principles into organisational cultures.
Where is improvement and change still needed?
I witnessed my mother’s frustration over inequality in the workplace. Decades later, some of that inequity still lingers on. I would like to see greater representation of women and minorities in leadership positions and on boards. From my perspective, more companies could also work toward fostering inclusive workplaces.
What advice would you offer to women entering the industry?
My strong advice to women is to seek mentorship, actively network, and advocate for yourself. I’d encourage women to be bold and take active steps to pursue opportunities and make their voices heard.
Would you encourage women to enter the sector?
I strongly recommend the re/insurance industry to women – it offers diverse career paths and opportunities for professional growth and impact.
Why is this industry great to work in?
The insurance industry offers intellectually stimulating challenges, global exposure, and the opportunity to make a meaningful impact on protecting people from risk.
Why is Bermuda a great place to be?
Bermuda has a strong regulatory environment, with Solvency II equivalency, qualified NAIC jurisdiction status and a reputable regulator. Our sector appreciates how Bermuda has demonstrated excellence and transparency with regards to money laundering, tax reporting, and economic substance. With a strong framework of intellectual capital and efficient incorporation and licensing processes, Bermuda presents itself as an appealing jurisdiction and will continue to attract new entrants in the life sector.
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