
Bridging the gender gap: the transformative power of mentorship
In the context of closing what can be a stubborn gender gap in the industry, mentorship has the potential to be a powerful lever – as many senior female leaders on both sides of the fence, will testify.
With insurance still considered a people-centric industry, talent development and retention should always be front of mind. For Bermuda, a global hub for risk and capital, the focus on cultivating strong, diverse leadership pipelines has never been more critical. Mentorship has the potential to be a powerful lever – not just for career advancement, but for empowering women to lead confidently and authentically in a male-dominated sector.
According to Deloitte’s 2024 ‘Women in the boardroom’ report, women hold 23.6% of board seats across Bermuda. While Bermuda’s re/insurance market has made strides in gender inclusion, leadership roles continue to be disproportionately occupied by men.
In Bermuda, organisations such as Women in Reinsurance (WiRe Bermuda) have created structured mentorship opportunities and safe spaces for women to share their experiences. Networks such as this hold a lot of potential for helping individuals progress in their careers.
Sandra DeSilva, founder, president and chief executive officer of Nova and Mythen Re, agrees with the foundational principles of mentorship, expressing that shared experiences and encouragement from others were fundamental to her career success.
What makes mentorship powerful?
Mentorship is more than coaching or guidance. It is a relationship built on trust, accountability and shared ambition. In industries such as re/insurance – where legacy knowledge, technical acumen and credibility are hard won – mentorship serves as a fast track to professional maturity and strategic insight.
According to CNBC/SurveyMonkey’s Workplace Happiness Survey, conducted in 2019: “More than nine in 10 workers (91%) who have a mentor are satisfied with their jobs, including more than half (57%) who are ‘very satisfied.’ Among those who don’t have a mentor, each of those numbers drop by double digits.” Those with mentors also reported feeling more valued and considered themselves better paid, two of the major factors contributing to job satisfaction. There was a 24% disparity among respondents regarding opportunities in their workplace, with those who had mentors responding more positively. The overarching message from the result was clear: Mentorship makes a difference no matter someone’s age, race or gender.
Mentorship can come in many forms, from senior to peer-to-peer and across industry or companies. The position of the mentor and mentee does not need to be aligned to be beneficial. For example, Deshay Caines, culture curator at Marsh McLennan, notes: “When women have men who are mentors or someone who takes them under their wing, what we see is those women tend to accelerate more, particularly in male-dominated environments.”
An additional benefit, reported by the Harvard Business Review, is the positive effect mentorship has on the mentor. Results showed that “people who served as mentors experienced lower levels of anxiety, and described their job as more meaningful, than those who did not mentor” (‘Stressed at work? Mentoring a colleague could help’, March 1, 2019).
Empowering through example
Effective mentorship isn’t about telling someone what to do – it’s about showing them what’s possible.
Yvette Pierre, chief policy and strategy officer, policy development, at the Bermuda Monetary Authority (BMA), reflected on the profound influence of her mentor, Eleen Lum, early in her career:
“I was fortunate to have Eleen Lum as a manager while I was a management trainee in underwriting. Eleen was an incredible mentor; a tiny, unassuming individual, yet she carried immense strength and grace. In those days when Diversity, Equity, and Inclusion (DEI) was not popular, as a female leader in a male-dominated profession, Eleen’s drive for excellence, her knowledge and expertise and her leadership style were compelling factors that caused her to “have a seat at the table”.
“She consistently demonstrated professionalism, putting people first and standing firm on her principles, even under immense pressure. Watching Eleen handle challenges with poise and unwavering commitment was inspiring. She showed me that true leadership is about integrity, consistency and walking your talk. It also showed me that true leadership comes at a cost, and I am not sure what kind of leader I would have become without her influence and example.”
Eleen’s mentorship highlights a critical truth: leaders don’t just shape businesses, they shape people. And when women see other women leading with integrity, they gain not only inspiration – they gain permission to lead as themselves.
Not all mentors are aware of their impact. Grace Sousa, of Ariel Re, shared a story that illustrates how mentorship often blossoms in quiet, personal moments:
“One woman who profoundly inspired me in my career is Vanessa Hardy Pickering. She entered my life at a crucial moment, offering mentorship that underscored the value of hard work and dedication. While she may not fully realise the depth of her influence, Vanessa showed me that it’s possible to thrive professionally while being a devoted wife and mother. Her example reminds us that women not only belong in this industry – we have a powerful voice, and we must never be afraid to use it.”
Vanessa’s example is a reminder that mentorship isn’t always formal or planned. Sometimes it’s a timely conversation, a shared lesson or the silent power of representation. These micro-moments compound over time, creating a legacy of empowered professionals who pay it forward.
Mentorship in action
Many companies are now implementing their own mentorship programmes, and there are many associations that also offer a platform to find mentors both through networking and formal programmes. But, with mentorship hailed as an inarguable positive, it’s time for more professionals to step up to the plate to assist the next generation.
AllVoices, an employee relations platform, explains that: “A fruitful mentorship not only elevates business performance but also opens up myriad opportunities for the mentees, fostering an environment of continuous growth and development,” published in ‘Mastering mentorship: your complete guide to becoming a workplace mentor, 2024’.
AllVoices describes key attributes of a mentor, which include active listening, strong communication and knowing when to provide encouragement and constructive criticism. The platform also suggests it’s important for mentors to be continuous learners themselves, dedicated to self-improvement, while also being able to foster independence in their mentees by guiding them, rather than providing them with all the answers.
Having an experienced mentor can come with the added benefit of a pre-made network. Introductions can soothe friction when trying to build a network, as trust is imparted from the pre-existing relationship.
Mentorship will look different for each individual, as we each have different needs. The relationship and its role should also develop along with your career. Mentorship can come in the shape of skill development, personal development, sharing experiences and examples, providing situational advice and feedback or simply providing a go-to for someone while they navigate daily life.
Everyone, no matter the stage, can benefit from having a mentor, even if just to bounce ideas off or request a second opinion. Particularly for women who might find themselves as one of few, or the only, females in the C-suite, for example, having a female mentor, whether lateral or horizontal, can offer immense support.
Empowering future leaders
As we’ve seen from the statistics above, mentorship can also be very rewarding for the mentor, offering the opportunity to make a meaningful impact on others.
Mentorship is more than professional guidance, it’s a transformative relationship that cultivates confidence, ambition and resilience. For women in Bermuda’s re/insurance industry, mentorship can create space not only to grow but to lead with purpose. It helps women navigate challenges, amplify their voices and see leadership as attainable, not aspirational.
The stories shared here – of mentors such as Eleen Lum and Vanessa Hardy Pickering – remind us that behind every successful woman is often another woman or ally who chose to invest their time, wisdom and belief.
As the industry continues to evolve, mentorship must become a strategic priority – not just for women, but for the organisations that want to attract, retain and empower top talent.
Whether formal or informal, structured or spontaneous, mentorship has a ripple effect that lifts individuals and strengthens teams with the ultimate power to drive business success.
By embracing mentorship as a tool for empowerment, Bermuda’s re/insurance sector has the opportunity not just to shape better leaders, but to inspire lasting change, one meaningful connection at a time. Now is the time to lead and to lift others as we do. So, to build a more inclusive and dynamic future, we must all ask ourselves: Whom can I mentor?
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