At Four Square we are passionate about insurance.

Founded in 1998, Four Square is a total benefits resource. We are in business solely to help companies, organizations, and individuals seamlessly manage insurance selection, benefits packages, strategic planning and compliance. 

Staff at Four Square.

How? First, we listen. Next, we research the best, most practical solutions and recommend the affordable benefits options to fit each individual client’s specific needs. 

And that is just the start. Our highly customized approach is designed to mitigate both business risk and personal stress.

Our customized solutions include:

• Insurance – Health, Dental, Vision, Life, Disability, and Medicare Supplements

• Benefits – Voluntary (e.g., Accident, Cancer); HSA/HRA/FSA Plans, and Telemedicine

• Management – Strategic planning, Client Portal, Open Enrollment, Employee Retention Strategy

• Solutions – Benefits Administration, Compliance, Employee Communication, Wellness Planning

Four Square Benefits, customized benefit solutions built from Square One. 

FAQs to consider when choosing your insurance agency: 

Q. Is there a real benefit in partnering with an independent agency? 

A. Absolutely! We represent our clients, not the insurance companies. This gives us – and you – access to solutions that are best for your specific situation. 

Q. What sets you apart from the competition?

A. Integrity, dependability, professionalism and responsiveness are in our DNA. Long after the “hype” of many of our competitors’ sales presentations fade, we’ll be here for you all year long, year in and year out. 

Q. With so many products out there, how do you know what to recommend?

A. We listen to you, then do the research most clients don’t have time for. Our custom proposal gives you everything you need to make an informed decision. 

Q. Why use an independent agency when seeking individual coverage?  

A. An independent agency can provide support, knowledge, and personalized recommendations based on each specific situation. We give our clients peace of mind knowing that their individual plan offers the best coverage at the most affordable price.

The Annual Open Enrollment for Individuals has been extended this year, beginning Nov. 1 and now ending Jan. 15. We are licensed to assist individuals in Maryland and Delaware with getting enrolled in coverage, along with creating a simple renewal process for the upcoming plan year. Let us work for you and be your direct contact for customer service. 

Four Square Benefits, where we do the shopping and you do the saving!

Four Square can be reached by calling Allie Creasy at 410.213.8338 x103 or

al***@fo****************.com











 and is located at 11944 Ocean Gateway Highway, Suite 5, Ocean City, MD 21842.