Gabrielle Hendrickson CWC, CWCL
Gabrielle Hendrickson is a Claims Manager with over 15 years of experience in the insurance industry, specializing in workers’ compensation claims, litigation strategy, and multi-state operations. Based in the Greater Orlando area, she currently leads a team of adjusters at AmTrust Financial, where she oversees claims reviews, client strategy, compliance discussions, and ongoing training initiatives. Her leadership approach centers on collaboration, accountability, and developing strong, capable teams.
Beginning her career in property management, Gabrielle transitioned into insurance after obtaining her license and starting in an entry-level support role. Through consistent dedication and hands-on experience, she advanced from medical-only claims handling to complex multi-state and catastrophic claims, eventually stepping into leadership roles across respected organizations in the field. Her career reflects steady progression built on adaptability, technical expertise, and a commitment to continuous learning.
Today, Gabrielle is recognized not only for her operational leadership but also for her contributions to the broader workers’ compensation community through industry associations, speaking engagements, and mentorship. She is actively involved with organizations such as CLM Alliance, NAAIA, and RISE Professionals, where she contributes to professional development and industry dialogue. Passionate about elevating others, she is committed to strengthening both her team and the future of claims professionals through education, mentorship, and leadership development.
• Certified Claims Adjuster
• Florida Board Certification in Workers' Compensation Litigation
• Valencia College
• Women Leading the way in Workers' Compensation
• RISE Professionals
• CLM Alliance
• NAAIA
• Orlando Claims Association
What do you attribute your success to?
I attribute my success to never giving up and always wanting to learn. It's super easy in insurance to get into one role and just stay in that role forever because you get comfortable - you get used to what you know, you get a groove going, you come in, do your job, and go home. But I never stop learning just because I feel like I've mastered what I'm currently doing. Once I know how to handle a desk, I learn a new state. Once I know how to handle the new state, I get a new skill, a new accreditation, some different credentialing. Each role has progressed in responsibility, and I've continued to move up because I always want to keep learning. I never like going into a role just to be okay at it - I always want to do well. So I'm constantly taking classes, going to conferences, and seeking out different learning opportunities as I progress through my career.
What’s the best career advice you’ve ever received?
The best career advice I ever received came from an older adjuster who had been doing this for a really long time and became a mentor to me when I was a young adjuster. She told me to never lose my smile when it comes to work. Insurance is pretty heavy - it can be really stressful, there are a lot of moving pieces, you never stop learning, and there's always something to do. But she said never lose your smile in that this is not who I am. I'm not defined by what I do for a living. Always finding joy in what I do allows me to keep my personality shining through my work. That's something I carry with me, and I also teach that and pass it on to other people as well.
What advice would you give to young women entering your industry?
Go for it. Whatever it is - whether it's a new role, a new skill, an accreditation, or something you want to master and you see a class for it - go for things that you don't quote-unquote think you are ready for or equipped to do. Just go for it. The worst thing that could happen is somebody tells you no, and no is never a bad thing. If you want it, go for it. Never undersell yourself, never doubt yourself or your skills. Be the best and go for what you think that you should have.
What are the biggest challenges or opportunities in your field right now?
The insurance industry is changing rapidly right now. Technology is advancing a lot faster than it was even 5 years ago, and AI is coming in everywhere - both in real life and in the insurance industry. So trying to keep up with all these changes is difficult, not just for myself but for the people in the industry with me. We also have a whole workforce change happening. We have a new generation of people coming into a role like insurance, which is not exactly glamorous - it's not Instagram-worthy, you know what I mean? It's not something that you would see people wanting to flaunt. So finding a way to bring this new generation into a role like an insurance adjuster is difficult. A lot of times when you go to conferences, people call it brain drain - we're losing talent. We're trying to find a way to get more people in, talk them into it, make it appealing, and give them the pros of coming to an insurance job. Losing talent is a huge issue right now in the insurance industry.
What values are most important to you in your work and personal life?
In both my personal life and in my employment, character and being a woman of your word is most important. Especially in this industry, or even outside in your personal life, people that are around you need to be able to expect you to be a woman or man of your word. In my employment, I have clients and employers and insurers that know if Gabby says, 'Hey, I'm gonna have that answer to you,' or 'I'm gonna get back to you by Friday,' or 'by end of business day today,' they know that I'm going to do that. In my personal life, my people know that if I say this is what I'm going to do, they don't have to double check, they don't have to keep reminding me - I am a woman of my word. I think that's very important in real life, your personal life, and your work life as well.