The Journey to Leadership: A Conversation with Greg Crabb

Amy Cooper, RISE Founder & CEO interviews Greg Crabb, CEO of Amerisure. Greg shares insights into his career journey and the relevance of his legal background in the insurance industry.

Amy Cooper: How did you get started in the industry?

Greg Crabb: When I was in law school at Emory University in Atlanta in my second summer, I applied and was selected into the Governor’s Internship program, and the program placed me with the State Board of Workers compensation.

I was working with the judges, the administrate law judges there. And candidly, what I was  mostly doing was helping write their opinions for them. They would give me some guidance, and then I’d write it and go from there. And then that actually became  a part time job in my third year of law school, where I still helped  draft some of their opinions. And so that led me to move into the insurance space after law school and, first legal, then claims, then underwriting, and strategy,

Amy: Do you feel like being a lawyer, having that background has helped you become a CEO or in any of your responsibilities now?

Greg: Yes, absolutely. I mean, we’re a heavily regulated industry, and so it’s helpful from that angle. And then there’s claims where having a legal background is helpful in understanding some of the complexity in the claims environment as well as some of the policy language and underwriting exposures.

But we have really good people who make the decisions. So it’s not that I’m making the decisions, but it helps, I think, to understand some of the risks and rewards.

Amy: What is the best piece of career advice that you ever received?

Greg: Yeah, so I think the best advice I received, and I know some people push against this, but is to follow your passion. And so for me, I have always tried to follow my passion.

For example,  when I was in undergrad, I was supposed to go into the business school after my sophomore year, but was more fascinated by the liberal arts. And so I chose to be a history major. And I remember having a conversation with my dad , telling him I wasn’t going to go in the business school, I was going to be a history major. And he said, you’re going to be digging ditches for the rest of your life and slammed down the phone.

I’ve followed that passion all the way from moving out of legal into claims, moving out of claims into an underwriting role, and then eventually ending up in this role. I also do remember having a passion to build things as well as to be in a leadership role to help make things better even before I was in insurance.

And so I’ve always followed that passion, and it hasn’t let me down.

Amy: Why is now the best time to start a career in insurance?

Greg: I think overall, people don’t recognize enough that insurance is a noble industry. We help people. We help businesses. We put lives back together. We help people in some of their darkest times of need. And so I do get invigorated by that noble cause from a macro standpoint.  

From a micro standpoint, there’s a lot of complexity in our business and we face many challenging decisions day in and day out in every aspect of what we do – be it risk management, underwriting, pricing a policy, or paying a claim or not. 

Also, there is the question of how our industry will evolve in such a complex, and ever changing world today. So all of those things get me excited to go into work, and I think it’s also why somebody should look at the insurance industry. You can be part of a noble profession.

There’s lots of growth opportunities for folks in all the different roles, and our industry is going to continue to be relevant into the future. There is always going to be a need for what we provide in terms of capital and services for the larger economy.

Amy: Do you want to do a plug on why people should want to work at Amerisure?

Greg: So Amerisure specifically, we win Best Places to Work in Insurance. Best and Brightest in the Nation.

Our employees are in our company’s mission so when we make decisions, employees are always front and center. And that leads to an employee value proposition that wants to help people grow, wants to help people succeed and creates an environment that wins those awards.  We are over 110 years old, but we are constantly challenging ourselves to be better.

Greg’s insights underline the significance of legal expertise in insurance, the value of passion in career decisions, and Amerisure’s employee-focused culture.