100 Women in Insurance

• 086: Underwrite Your Career: From London to Bermuda with Hannah Greenwood

  This episode is sponsored by Fidelis Insurance Group Summary In this episode, Sandra speaks with Hannah Greenwood, Group Chief of Staff and Chief Underwriting Officer (Bermuda) at Fidelis Insurance Group, about how curiosity, courage and consistency shape a global career. Hannah shares how a Lloyd’s of London internship led her into insurance, how broking taught her the value of team culture and ego-free leadership, and how curiosity opened doors to strategy and M&A. She reflects on staying long enough in one firm to build goodwill, taking on stretch roles that expanded her perspective, and moving from London to Bermuda to help drive underwriting strategy and partnerships. They discuss how sponsorship grows through consistent delivery, the benefits of taking calculated risks, why you should “underwrite” your own career by gathering information, testing fit, and adjusting as you learn. Hannah also talks candidly about balancing leadership and motherhood, the myth of the perfect time for big life decisions, and the advantages of Bermuda’s concentrated, senior market. Takeaways Deliver excellence first. Strong performance in your current role builds credibility and sponsorship naturally Consistency earns trust. Sponsors appear when people see you deliver results repeatedly Curiosity opens doors. Asking questions and exploring projects beyond your remit expands your perspective Longevity creates advocacy. Staying with one organisation long enough builds goodwill and career champions Take calculated risks. Growth often comes from stepping into roles before you feel fully prepared Listen widely, decide independently. Advice helps, but only you know what’s right for you Build layered networks. Supportive relationships sustain you, and transactional ones advance you Leadership without ego scales influence. The best leaders invest in others and create room for growth Mobility accelerates learning. Working abroad, especially in smaller markets, can deepen exposure to strategy and leadership Balance is ongoing. There’s never a perfect time for big life choices, but structure and support make it possible. Career progression often follows a narrow path; seek diverse experiences Great leadership invests in people and keeps ego out of the room About the Sponsor About the sponsor Fidelis Insurance Group Fidelis Insurance Group is a global specialty insurance and reinsurance company focused on creating value through strategic capital allocation, expert risk selection and a network of long-term underwriting partnerships. We have built a strong foundation for scale and profitable growth, underpinned by our disciplined approach to risk selection and our financial strength, which is reflected in our insurer financial strength ratings of A from AM Best, A- from S&P and A3 from Moody’s. Our network of underwriting partners and highly diversified portfolio enable us to proactively navigate market cycles, offer innovative and tailored solutions, capitalize on favorable risk-reward opportunities and produce superior returns for shareholders. Our network of underwriting partners and highly diversified portfolio enable us to execute our strategy of proactively navigating market cycles, offering innovative and tailored solutions, capitalizing on favorable risk-reward opportunities and producing superior returns for shareholders. For additional information about Fidelis Insurance Group, our people and our products, please visit our website at www.FidelisInsurance.com. About the guest Connect with Hannah Greenwood on LinkedIn. Hannah currently serves as Group Chief of Staff, Bermuda Chief Underwriting Officer and is a member of the Executive Leadership Team. Prior to joining the company in 2023, Hannah served as Business manager for Ardonagh where she worked with the CEO of their Capital Solutions arm. Hannah started her career at Lloyd’s before becoming an energy broker at independent NMB, latterly renamed Ed. In 2020, she took on a more strategic role supporting the CEO of the business, with a focus across Specialty lines. Hannah holds a BA in Politics, Philosophy and Economics from the University of Durham, an MBA from Warwick Business School and is ACII qualified. About the host Connect with Sandra Lewin on LinkedIn. Sign up to ‘Coffee with Sandra’ to stay up to date with 100 Women in Insurance. Join ‘The Pink Book’ Collective, a private LinkedIn group connecting women in insurance with mentors, speaking opportunities, and community. Learn more about the 100 Women in Insurance Collective: www.100womenininsurance.com/collective.

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• 085: How to Achieve the Career You Want, Not the One You Need with Rebecca Fuller

  This episode is sponsored by Full Circle Communications. Summary In this episode, Sandra Lewin speaks with Rebecca Fuller, about choosing the career you want, staying curious at senior level, and why courage comes before confidence. Rebecca shares how moving from fitness to insurance shaped her approach to leadership, why motherhood helped her step into bigger roles, and how knowing your strengths and gaps builds better teams. Together they discuss public speaking, preparation, and self-reflection. Rebecca explains why women’s networks matter, how to build professional networks in male-dominated rooms, and why you should stop “breaking into the boys’ club” and create your own. Be courageous and confidence will follow. Stay curious. Make deliberate choices that fit the life you want. Takeaways Growth does not stop at senior level. Keep learning, keep testing yourself Motherhood can be a catalyst for leadership and clearer choices Choose the career you want, not the one you think you need Courage comes before confidence. Action builds belief Preparation improves performance. Script, rehearse, use the mirror, and practise silence Know your strengths and weaknesses. Hire, listen, and delegate accordingly Do not chase the “boys’ club”. Create your own spaces and shared interests Show up for networking with presence. Diversify how you connect Lead your priorities. Reassess quarterly, refocus, and let some things go Feeling valued and heard keeps talent engaged more than pay alone About the guest Connect with Rebecca Fuller on LinkedIn About the host Connect with Sandra Lewin on LinkedIn Sign up to ‘Coffee with Sandra’ newsletter to stay up to date on all 100 Women In Insurance and more. Join ‘The Pink Book’ Collective, private LinkedIn Group connecting women in insurance to find mentors, speaking opportunities and much more. Learn more about the 100 Women in Insurance Collective: www.100womenininsurance.com/collective

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• 084: Your reputation travels faster than you do, so how do you protect it? with Kelly Nwankwo

  Summary In this episode, Sandra speaks with Kelly Nwankwo about belonging, curiosity, and the power of reputation in building a meaningful career. Kelly reflects on her twists and turns throughout her career, which were a combination of reflection, plan and openness to try. Her journey through broking, into consulting, and back to the market is a testimonial of how our careers can take unexpected turns. Through these shifts, Kelly learned how reputation, relationships, and self-awareness shape long-term success. Together, Sandra and Kelly discuss personal brand and authenticity, exploring how to adapt to new environments without losing yourself. Kelly describes authenticity as something you can “dial up or down,” depending on context, but never perform. She also explains how curiosity and courage open new doors and how showing up consistently builds trust and visibility. Kelly highlights networks like LTL, ACIN (now known as Equity), and iCAN, which gave her both support and lifelong friendships. She believes that belonging is what keeps people in the industry and that inclusion helps people thrive once they arrive. She also shares her view that ambition should be tied to learning, not titles, and looks ahead to a more diverse, technology-driven future for insurance. Takeaways Career paths evolve through curiosity and courage Your reputation travels faster than you do, protect it A strong personal brand is built through visibility, consistency and authenticity Mentors and peers shape how you grow and lead Professional networks build belonging and confidence Managers can nurture ambition by creating space for learning Ambition tied to learning drives sustainable growth AI will reshape work, but human connection will always matter Fulfilment comes from purpose, progress, and the people around you Diversity in the workplace enhances the overall experience and retention Community and friendships formed through networking can be lifelong Diversity brings people in, but inclusion keeps them About the guest Connect with Kelly Nwankwo on LinkedIn. About the host Connect with Sandra Lewin on LinkedIn. Sign up to ‘Coffee with Sandra’ to stay up to date with 100 Women in Insurance. Join ‘The Pink Book’ Collective, a private LinkedIn group connecting women in insurance with mentors, speaking opportunities, and community. Learn more about the 100 Women in Insurance Collective: www.100womenininsurance.com/collective.

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• 083: Why Haven’t We Achieved Gender Equality Yet with Abbey Atkinson

  Sign up to Coffee with Sandra to stay up to date with all things 100 Women in Insurance. Summary In this episode, Sandra Lewin speaks with Abbey Atkinson about what really holds women back from progressing into senior roles in insurance. The conversation goes beyond quick fixes or skills workshops and looks honestly at the systems, structures, and habits that still shape how organisations work. 🚨 It is not a woman problem. Abbey shares insights from her PhD research, exploring how culture, power, and trust influence progression. She explains the concept of role habitus and how some jobs are designed around old norms, forcing people to adapt themselves to fit. Together, Sandra and Abbey discuss how trust operates differently for women, why flexible working can sometimes become overwork, and what needs to shift for change to be genuine. The message is clear: women don’t need fixing. The system does. And if we create the right environment, there is plenty of food at the table for everyone to eat. Takeaways Progression barriers are mostly cultural and structural, not about women’s capability Role habitus explains how certain roles carry built-in behaviours that favour dominant norms Women often need to re-earn trust repeatedly, while men’s trust tends to remain intact Flexible working can help, but without boundaries it often leads to invisible overwork Women juggle both professional and personal networks, adding unseen emotional labour Women-centred networks are valuable, but they need links to decision-makers to drive change Networking should be treated as a skill and supported equally across the business Employee groups need proper funding and leadership buy-in, not just goodwill Honest dialogue from leadership matters more than polished surveys or policy statements True equality means redesigning systems so everyone has room to contribute About the Guest Connect with Abbey Atkinson on LinkedIn Read her latest article, Why We Haven’t Yet Achieved Equality, part of her Bringing a New Beat to Equality series. Abbey’s research challenges the idea that women need to change to progress. Through her work with Insight Change and her academic research, she focuses on how culture, trust, and role design can either open or close the path to leadership. About the Host Connect with Sandra Lewin on LinkedIn Sign up to Coffee with Sandra to stay up to date with all things 100 Women in Insurance. Join The Pink Book Collective, a private LinkedIn group connecting women in insurance to mentors, speaking opportunities, and community. Learn more about the 100 Women in Insurance Collective: www.100womenininsurance.com/collective

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• 082: The One Rule You Should Never Break in the Insurance Industry with Jacqueline Sinclair

  Sign up to Coffee with Sandra to stay up to date with all things 100 Women in Insurance. Summary In this episode, Sandra Lewin speaks with Jacqueline Sinclair about how careers can begin by chance, why integrity and connection matter more than ever, and how success evolves as we grow. Jacqueline shares how her first interview in London didn’t go quite as planned, but ultimately led to a rewarding career built on curiosity and adaptability. She reflects on what she’s learned from working across both startups and established organisations, and how her focus has shifted from personal milestones to developing others and building teams. Together, Sandra and Jacqueline explore the realities of the gender pay gap, the growing number of women designing work around their lives, and why flexibility has become a powerful form of leadership. They also discuss how to network as an introvert, why small acts of courtesy go a long way, and what the rise of AI means for the future of work and inclusion. It’s a conversation about values, change, and the courage to shape a career on your own terms. Takeaways Careers often start by chance; purpose is built through experience Success evolves from individual achievement to collective growth Flexibility and autonomy create space for better balance Courtesy and reputation matter in a small, connected industry The gender pay gap widens mid-career and needs deliberate action Networking can be one-to-one and rooted in genuine curiosity AI is transforming how we work, but human insight remains vital Diversity in AI and leadership helps prevent bias and drive fairness The insurance industry offers wide and varied opportunities for all About the guest Connect with Jacqueline Sinclair on LinkedIn About the host Connect with Sandra Lewin on LinkedIn Sign up to Coffee with Sandra to stay up to date with all things 100 Women in Insurance. Join The Pink Book Collective — a private LinkedIn group connecting women in insurance to mentors, speaking opportunities, and community. Learn more about the 100 Women in Insurance Collective: www.100womenininsurance.com/collective

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