Five minutes with…Jayson Grossman, Procover professional lines manager and head of casualty at Steadfast Underwriting Agencies

Q. What is your current role?

I’m head of casualty at Steadfast Underwriting Agencies, which means I oversee the financial lines and general liability space. I’m also professional lines manager at Procover.

Q. Why did you choose to work in the insurance industry?

A. I didn't really know what I wanted to do for a career and when I left school it was during the recession of the early 1990s when unemployment among young people was about 55%. Initially I was just looking for some part time work, and my father was a senior executive at AIG so I started as a clerk and administrator in the accident and health division in about 1995. Then I just progressed from there.

Q. What other roles have you held during your time in insurance?

A. I left AIG in 1999 and travelled overseas for a while as I wasn’t sure I wanted to stay in the industry. But when I returned to Melbourne, I got a role with underwriting agency Dexter in IT liability. I was then tossing up a move to London for work, but Dexter tapped me about moving with them to establish an office in Sydney which I did, and I haven’t left Sydney since.

In 2005, however, I moved across to Zurich as a financial lines underwriter before again reassessing my career in insurance during another stint of overseas travel in 2009. When I returned to Australia I joined Miramar in financial lines in 2010, and helped Steadfast roll out Miramar’s financial lines business and rebrand it as Procover in 2014, and I’ve been there ever since. I like to have a bit of fun and I think, for the most part, people have enjoyed working with me and for me.

Q. What advice would you give to people considering a career in insurance?

A. Many people fall into insurance like I did, and despite my initial regrets about insurance and twice trying to leave the industry I’m glad I didn’t. It’s a wonderful, social industry, with huge amounts of opportunity, you can travel with it and your skills are transferable all around the world.

Q. What do you enjoy doing when you’re not working?

A. I like to travel, and have played basketball, golf, and surfed and bushwalked a bit, but these days with two young kids that’s a bit limited. Now’s it’s all about family.

To contact Jayson, head of casualty at Steadfast Underwriting Agencies and professional lines manager at Procover you can email him at


Procover Underwriting Agency Pty Ltd (an AR of Miramar Underwriting Agency Pty Ltd) acts under binding authorities as agent for the insurers of the product under a coinsurance arrangement between certain underwriters at Lloyd’s and HDI Global Specialty SE – Australia.