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2018 Break Out Awards, Midwest: Justin Gress

2018 Break Out Awards, Midwest: Justin Gress


Director of strategic operations for XL Catlin Canada and North American construction

XL Group Ltd.


Age: 34

Justin Gress joined XL Group Ltd., which does business as XL Catlin, in October 2013 and now serves a dual senior management role, charged with driving the overall operational plan, strategic initiatives and execution. Previously, Mr. Gress was the operations/strategic initiatives leader for XL Catlin’s distribution and network Americas team and central broker management. XL Catlin credits Mr. Gress with helping to lead the conversation about attracting more millennial talent to the insurance industry. He recently presented on the topic at the Millennials in Insurance 2018 conference in Toronto.

Job change over the next 10 years

Operational roles are blending together. Ten years from now, you will see the (chief operating officer), (chief information officer) and chief processing officer merge into a hybrid role built around technology, data and the ability to motivate people globally and locally in an effective way.

Advice to someone starting in the business

First, don’t be afraid to get involved or underwrite a new product or take on a new role. Second, find a great boss who encourages you. Third, the faster you can figure out what the culture is and what kind of culture you like, the quicker you can grow in an organization.

Best-kept secret about insurance

The opportunities. It’s an industry that is ripe for some serious change … Innovation and change are just starting, (and) the next five to 10 years are going to create so many interesting opportunities.

Something people don’t know about you

That I am 34.

Dream vacation

Exploring Eastern Europe. I have been all over the world but would like to go to Budapest, Prague, etc., next.

Favorite meal

A filet at RPM Steak Chicago


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