Navigating the Insurance Industry: A Q&A with Emerging Leader, Greg Hawbaker

Discover Greg Hawbaker's compelling career journey in the insurance industry, from handling automobile claims to becoming a Claims Director at Skyward Specialty. Named a 2025 Emerging Leader by APCIA, Greg shares his keys to success, valuable career lessons and insightful advice for aspiring leaders in the industry. 

Q1: Tell us about your career journey and what led you to your current role 

I started my career handling automobile claims, both at the desk and in the field writing property damage estimates. I later sought out a position managing general liability claims, but the real learning and career development began when I was provided an opportunity to work in the excess and surplus (E&S) realm. That is where I had the opportunity to be exposed to multiple lines of business and policy forms and able to delve into complex coverage matters. I developed relationships that enabled me to build a network of peers and mentors, which ultimately led me to Skyward Specialty. 

Q2: What do you believe has been the key to your success and recognition as an emerging leader in the industry?   

A reputation of high integrity, dependability and a strong work ethic. I take pride in my work and don’t compromise. I do what I say I am going to do and take the initiative to do my best.  

Q3: What are some of the most important lessons you’ve learned in your career so far?

Stay humble and be grateful. I’ve learned a lot over the years thanks to many great peers and mentors who have shared their wisdom with me, but I still have much to learn and do not consider myself an expert at anything.  

You can learn from anyone in any position or walk of life. Do not make assumptions or draw conclusions without all the facts. I’ve had to check myself on multiple occasions when I thought I knew the whole story before hearing the whole story.

Q4: How do you stay up to date with industry trends and continue to grow professionally?  

Continuing education is and always will be important, but I also find that collaboration in learning goes a long way. I handle claims across the country, and a great way to get the pulse on what’s going on in a particular region is by connecting with people who are there, such as retail agents, brokers and attorneys. Additionally, the opportunities I’ve had to work for carriers that encourage communication between claims and underwriting have been of great value to me. 

Q5: What advice would you give to others who aspire to become leaders in the insurance industry?   

Do your best work. Be thorough and efficient, but be cautious not to get caught up in unnecessary minutiae. Take the time to plan and prioritize your day, and when the day is done, rest. Balance is important. Quantity does not equal quality. When you take the time to rest and clear your mind, you are better prepared to do your best work the next day.