Courtney Greenstein

Senior Account Executive
Brown & Brown
Boston, MA 02108

Courtney Greenstein is a Senior Account Executive at Brown & Brown, where she specializes in employee benefits and medical insurance funding arrangements. Based in Greater Boston, she partners with organizations to design strategic benefits packages that balance cost control with comprehensive employee coverage. In her role, she helps clients navigate complex insurance landscapes, including budgeting, pricing strategies, and plan optimization to support both business goals and employee well-being.

With nearly two decades of experience in the employee benefits industry, Courtney has built her career through progressive roles in account management and benefits consulting. She spent many years at Cross Insurance, where she developed deep expertise in benefits analysis, client relationship management, and long-term plan design. Her career growth reflects a combination of hands-on industry experience, mentorship, and continuous self-driven learning, allowing her to evolve into a trusted strategic advisor for her clients.

Courtney earned her education from the University of Massachusetts Lowell, where she studied business and built a foundation in analytical thinking and client service. She is known for her collaborative approach, empathy, and commitment to helping employers create meaningful, sustainable benefits programs. Passionate about problem-solving and lifelong learning, she continues to focus on delivering practical solutions that improve access to care and support workforce stability in a rapidly changing healthcare and insurance environment.

• Licensed Insurance Professional
• Communicating Nonverbally
• Developing Self-Awareness

• University of Massachusetts Lowell- B.B.A.
• University of Massachusetts Lowell- A.S.

• The Power of She (Women's Mentorship Program)

• Theater Program Support (Past)

Q

What do you attribute your success to?

I attribute my success to my affinity to learn and my drive to be successful for myself and for my children, to give them what they deserve in life. It took me a long time to get to where I am today, but that doesn't matter because they're still my babies. I worked hard to get myself to the point where I am today, and now that they're young adults, it allows me to help them get to the next step and give them the support that they need. I lead with empathy in every aspect of my work, combining deep technical insurance knowledge with strategic consulting and relationship management. I see myself not just as a service provider, but as a trusted thinking partner. I'm highly skilled at translating complex legal and technical language into clear, understandable guidance for clients. Building strong personal relationships with both clients and vendor partners is central to my approach. Above all, I credit my integrity, loyalty, commitment, and nonjudgmental mindset as the foundation of my professional achievements, along with maintaining an always learning mindset.

Q

What’s the best career advice you’ve ever received?

The best career advice I've ever received is to always learn and continue to enrich yourself, whether it be within the industry or with anything. Just keep learning. I think that's the most important thing. Never stop, because it stimulates your mind, it makes you have connections and networks, and it's just important for your personal and professional growth.

Q

What advice would you give to young women entering your industry?

Don't be afraid to ask questions. If you don't know something, there's always somebody who can help you get the answer. Don't be afraid to say to your customers or your clients, if they ask you a question and you don't know the answer, don't be afraid to say 'I don't have that answer right now, but I will get it to you.' Don't be afraid to come to people and ask. Most everybody is willing to help you and wants you to succeed.

Q

What are the biggest challenges or opportunities in your field right now?

There is plenty of opportunity in my field right now. Thankfully, it's an industry where people are needed. You can go into this industry at a very green level and learn, as long as you're willing to learn. If you want to get your license in this field, it's not a difficult thing to do. I passed it on the first try, and you just gotta do the work and put the studying in. You don't necessarily need your college degree, though it helps, especially in Massachusetts where we're a more competitive region when it comes to the job market. For the challenges in my industry, we don't have enough people, that's one of the challenges. The industry itself is trying to help our customers with this difficult landscape of health insurance and pharmacy. It is incredibly difficult, and we're always trying to be innovative and find solutions to help mitigate costs and make sure people get what they need and get the care they need. You don't ever want people to not get their care based on the fact that they can't afford it. That's important for us to be able to do that for our clients. We've had some success, we've had some failures, as with anything.

Q

What values are most important to you in your work and personal life?

My most important value is empathy, to understand others and to walk in their shoes without judgment, to look at things from all angles and understand that most people do things, and if they do something that's sort of a negative thing, it's usually unintentional. My other attribute that I strongly feel about is loyalty, being loyal to yourself, being loyal to your cause, being loyal to who you align with professionally and as a friend. That would probably be the one thing that people say that I am, that is my biggest attribute, is my loyalty. Lastly, I think it's important to be nonjudgmental. I think that goes along with empathy too. If you're looking at things from all angles and understanding people, it allows you to put your judgment aside. As a single mother of now young adult children, my greatest priority has always been providing them with emotional and financial support so they can pursue their goals. My children remain the most important part of my life and a constant source of purpose and motivation. I'm deeply grateful for my supportive tribe of friends and family who stand by me through every stage of life. With them, I share a love of live music, hiking, and nature. These experiences help me restore, recharge, and maintain balance.

Locations

Brown & Brown

One Beacon Street, 17th Floor, Boston, MA 02108

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