SIFM Spotlight 2024 – Rory Rose

SIFM Young Professionals represent a growing and dynamic group within our organization. “Spotlight 2024” articles are a series of interviews with some of these outstanding young leaders in the insurance industry.

Here’s what Rory Rose has to share:

UNIQUE INSIGHTS

I view working with teams from other divisions or groups not as challenges but as opportunities. Fairfax’s decentralized structure presents a tremendous chance to collaborate across its various sister companies, allowing us to leverage best practices, and to benefit from sharing and exchanging ideas.

LEADERSHIP

At the core of my leadership is a simple concept: if I can make myself no longer needed, then I’ve been successful. My leadership skills have developed over time through experimentation, trial and error. I believe a successful leader must not fear failure, as it offers valuable opportunities for self-reflection, learning and growth, allowing for adjustments in approach. As Einstein aptly said, “Anyone who has never made a mistake has never tried anything new.”

As a leader, I make it a point to understand what motivates each person and tailor my approach to effectively support and engage different age groups. While I never had a mentor myself, I have taken on the role of a mentor. I find it incredibly rewarding to influence and shift the perspectives of my mentees, helping them to independently work through complex issues they initially believed they couldn’t solve on their own.

RESPONSIBILITIES

I’m the CFO of Hudson Insurance Group, which is the US Insurance Division of Odyssey Group, a subsidiary of Fairfax Financial Holdings LTD. My role can be categorized into three core responsibilities: Strategic Business Partner: collaborating with the executive committee to support and implement strategic initiatives. Financial Reporting to Odyssey Group: ensuring that accurate and timely financial information is provided. Transformation: upskilling and transforming the finance function to enhance value creation and ensure scalability as Hudson continues to grow.

2024 VISION

Commercial specialty insurance is facing several significant challenges including climate change, geopolitical risk, social inflation and talent acquisition/retention. Updating pricing strategies and risk models to address the claims management processes as well as addressing the legal frameworks that impact the industry are imperative. With the industry facing a talent gap as experienced professionals continue to retire, the opportunity to nurture the next generation of industry leaders is essential.

SUCCESS PATHWAY

Originally from Queens, I now split my time between Brooklyn and Long Island. When not working, I spend my time with family and friends, enjoying the vibrant restaurant and nightlife scene that New York offers. I also cherish quiet moments at home, binge-watching my favorite TV series and spending quality time with my wife and our one-year-old. Now, I find myself frequently singing along to Mrs. Rachel’s hymns.

My father was an appeals officer for the IRS, which certainly influenced my career choice. I excelled in math during high school and entered the honors program at the University of Delaware, where I majored in accounting. I didn’t initially plan to stick with the major, but the coursework came naturally, and I found myself excelling.

Like many in the industry, insurance wasn’t a conscious choice. Initially I focused on roles in the financial services sector, but came across an opportunity at QBE, where their Americas division was looking to fund a series of acquisitions. The chance to work on M&A projects was appealing to me.

As I approach 20 years in the industry, my perspective has evolved. Insurance is one of the oldest industries in the world and plays a crucial role in helping people and companies manage risk — the aspect of the industry which I find most intriguing.

Looking ahead, I am excited about expanding my contributions in a broader, more international role within Odyssey, where I plan to apply the same approach across the wider organization.

What excites me most about working at Hudson is the culture. Despite the decentralized nature of Fairfax and its subsidiaries, a shared culture permeates all operations, and their guiding principles continue to shape our culture. While it might sound cliché, these principles genuinely drive our approach to serving employees, customers and communities.

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