Insurance Unfiltered: Real Stories and Bold Career Strategies

The insurance industry is built on the cold calculation of risk, yet for many Black professionals, the most significant risks aren’t found in a policy, they are found in the boardrooms where potential is weighed against a glass ceiling that feels more like reinforced concrete. To thrive in this space, we must confront the "unfiltered" reality: the exhaustion of navigating microaggressions dismissed as "office culture" and the systemic bias that quietly excludes talented voices from the decision making table.

Breaking through isn’t just about working twice as hard; it’s about a bold strategy of visibility. We must stop asking for permission to lead and start building the psychological scaffolding that supports our own brilliance. This means finding sponsors who will say your name in rooms you haven’t entered yet and mastering the "human commercial" paradox, staying authentically human while driving ruthless commercial value.

The struggle is real, but the strategy is bolder. We overcome bias by becoming undeniable, turning every "no" into a data point for our inevitable success. By ensuring that when we finally shatter that ceiling, we leave the door wide open for the next generation of leaders to walk through without the armor we had to wear, we change the industry: one bold, unfiltered career at a time.

About Beazley

Beazley is a leading global specialist insurer with a reputation for tackling complex risks and pioneering innovative solutions. Headquartered in London and a prominent member of the Lloyd’s market, Beazley operates across Europe, North America, and Asia, focusing on diverse areas such as cyber risk, marine, political risks, and speciality liability.

Beazley is committed to more than just industry leading underwriting; they are actively championing a culture where diversity of thought is a core business strategy. Their involvement in this conversation is driven by a mission to recruit, retain, and develop talent from all backgrounds, ensuring that every professional has the opportunity to thrive at every level of the organisation.

• Targeted Representation: Beazley has set clear, measurable goals for inclusion, including a commitment to increase the representation of People of Colour in senior leadership to 17% by 2027.
• Employee-Led Networks: They foster a truly inclusive environment through active internal groups like Beazley RACE (Racial Awareness and Cultural Equality), which provide platforms for employees to share their voices and influence corporate culture.
• Bold Values: Guided by their core value of "Being Bold," Beazley isn't afraid to confront the "unfiltered" challenges within the insurance sector, from glass ceilings to the everyday impact of microaggressions.

MEET THE SPEAKERS

Jon Perry, Midwest Regional Manager, US Executive Risk.

Jon Perry is an underwriter and the Midwest team lead for US executive risk at Beazley in Chicago. He also serves as Head of the Chicago office. Perry entered the insurance industry in Travelers’ Underwriting Professional Development program after graduating from the Katie School of Insurance at Illinois State, then worked on the D&O team at Allied World before taking on his current role. He is an alum of the Professional Liability Underwriting Society’s Leadership and Mentoring Program. In addition to his work as an underwriter, Perry is passionate about recruiting and developing young talent in the industry. He served as a member of Gamma Iota Sigma’s board of trustees and volunteers as a mentor to students, helping to foster their interest in insurance.

Ricky Benjamin, Senior HRBP to Underwriting Teams

Ricky Benjamin is a Senior HR Business Partner at Beazley with over 20 years of leadership experience across financial services, people strategy, organisational design and inclusion. After graduating with honours in Mathematics with Computer Science from Brunel University, he built a successful career in retail banking before transitioning into HR leadership, where he now partners with senior leaders to drive organisational effectiveness and shape inclusive workplace cultures.

During his time at TSB Bank, Ricky designed and led the award-winning Ignite programme, helping Black and Black mixed-heritage colleagues build career confidence and progression while supporting allies to create more equitable workplaces. His work continues to focus on unlocking talent, developing leaders and creating environments where people can thrive.

Alongside his corporate career, Ricky is a passionate advocate for social mobility and has mentored through organisations including the Miranda Brawn Diversity Leadership Foundation, Reach Society and the Social Mobility Foundation. As a speaker, he brings a powerful combination of commercial leadership experience and lived experience, sharing insights on leadership, inclusion, career progression and unlocking potential.

The conversation is shifting and this is your chance to be part of the movement redefining the future of insurance. Whether you are looking to sharpen your career strategy, navigate complex workplace dynamics, or connect with a community that understands your journey, this event is designed for you.