James Underwood

License #: 18607458

4.9 OUT OF 5 STARS

(59 Reviews)

Christopher Draegert

License #: 16765125

4.9 OUT OF 5 STARS

(107 Reviews)

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About James

With over 6 years of industry experience, I am committed to providing my clients with accurate insurance solutions, informed decision-making, and competitive rates. I take the time to ensure that my clients have a comprehensive understanding of their insurance coverage and explore all available options. As an independent agent, I have access to an extensive network of 40+ insurance companies, allowing me to thoroughly shop rates and find the best fit for my clients' needs. My passion for insurance extends beyond my professional life; I am an insurance nerd who stays up-to-date with the latest industry trends and regulations. My goal is to empower my clients by equipping them with the knowledge they need to make confident insurance choices. Trust me to guide you through the insurance process, providing meticulous attention to detail and unwavering dedication to your insurance protection.

States Licensed In: IL, WI

About Christopher

With over 10 years of industry experience, I am dedicated to providing exceptional insurance services. My priority is to ensure that my clients have a clear understanding of their insurance coverage and available options. I believe that informed clients are empowered to make better decisions. As an independent agent, my access to an extensive network of more than 50 insurance companies, paired with my in-depth knowledge of the insurance industry, enables me to identify the most suitable solutions tailored to my clients' unique needs and budget. Insurance is not just a profession for me; it's a passion that I live and breathe every day. With my commitment to outstanding customer service, backed by Goosehead and our amazing support, I strive to make the insurance process seamless and transparent. Trust me to be your insurance advisor, guiding you towards comprehensive coverage that protects what matters most to you.

States Licensed In: IL, WI

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100 North Waukegan Road, Suite 209
Lake Bluff, IL 60044

(847) 447-2206

Languages spoken:
English

Hours:

We’ve got you covered,

and then some.

Homeowners Insurance >
Auto Insurance >
Flood Insurance >
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You probably looked at several houses before you found the right fit; why not look at home insurance the same way? Goosehead does the looking for you, and finds the policy that fits your needs and budget, without compromising coverage.

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It seems like there’s as many car insurance companies out there as there are cars. Lucky for you, Goosehead looks under the hood of all those policies to find the right coverage for you and your ride. Think of us as your roadmap to better protection and better rates.

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Having the right amount of protection in case of flooding is important. That’s why our Goosehead experts will do all the research for you. We’ll compare dozens of plans and choose what’s best for your residence, and your budget.

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Sure, you may not own the building. But you own what’s in it. If a fire or disaster would cause a major setback, take a close look at renters insurance. Better yet, let us do it for you. We’ve evaluated products from dozens of the most respected insurance companies to help you home in on the right policy.

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From an insurance standpoint, high rises, townhomes and condos can be, well, a little different. HOAs cover some parts of the property, leaving other areas up to you. We can help you find a policy that provides the coverage you need — at rates you’ll feel right at home with.

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A rental property isn’t the same as a primary residence. Without proper protection, a landlord might be personally liable for damages from accidents or other events. We can help you determine the right coverage for your rental properties and compare rental property insurance quotes so you can operate with total peace of mind.

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Driving a motorcycle is all about freedom. Speaking of freedom, there’s no need for you to spend end less hours of your free time comparing insurance plans. Comparing the best motorcycle policies from the best insurance companies to get you protected the way you should be protected, at the price you deserve.

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Chances are you bought a boat for a little rest and relaxation. Goosehead makes shopping for boat insurance just as relaxing. Our expert agents will shop dozens of policies and find you the right protection, at the right price, that will really float your boat.

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Your RV lets you escape to the open road. And with Goosehead, you can escape the usual time commitment of buying insurance. Our expert agents do the research for you, comparing dozens of policies and choosing the right protection for you and your home on wheels, all at the price you deserve.

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As the saying goes, life happens. But sometimes it happens in ways we don’t expect. For all the great times, and the more difficult times, Goosehead can be there to make sure you and your family are prepared, and protected. If something happens to you, the right coverage will ensure your family is financially secure and well taken care of in your absence.

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HOMEOWNER INSURANCE

Water Coverages Explained

Four different types of water coverage may or may not be part of your home insurance policy. Let’s look at how they could help better protect you and your family from financial burden due to various causes of water damage to your home.

Recent Reviews

Total Agency Reviews 166

John B., 2/18/2025 2:49:28 PM

Christopher the Agency owner is professional and does an excellent job of explaining and follow up.

Brenda N., 2/11/2025 2:12:57 PM

very detailed and informative. Looking forward to working with him

Angela R., 1/5/2025 9:17:07 PM

Christopher explained everything very well and clearly and was able to answer all my questions. Thanks to Christopher, I know have a better coverage for my Home and Auto insurance.

Rebecca S., 12/27/2024 1:40:41 PM

James is extremely understanding of working around children and was very thorough in his explanation of coverage options. Some things I had never had explained before.

Heather V., 12/21/2024 2:48:15 AM

Christopher was very timely and thorough.

Mark A., 12/10/2024 4:17:28 PM

James did a great job and was patient while we had him jump through hoops

Rita V., 10/3/2024 12:36:12 PM

Cost

Claire C., 10/3/2024 2:17:02 AM

I'm a bit of an over-explainer myself, so I really appreciate that Chris took the time to explain every little detail of our policy and answer every question that my fiancé and I had. He also found us a great deal that we likely wouldn't have been able to find on our own. Thanks, Chris!!!

Kati H., 9/30/2024 3:52:06 PM

James was incredibly easy to work with. Answered all of our questions and gave us honest feedback.

Kristin S., 9/25/2024 5:06:35 PM

Very helpful, efficient & friendly!

Julie S., 9/19/2024 12:13:04 AM

James was helpful and thorough.

Elizabeth B., 9/18/2024 4:22:51 PM

James was great to work with!!!

Todd V., 9/6/2024 9:57:33 PM

Great pricing and Christopher met my needs.

Becky M., 8/26/2024 12:07:30 AM

Agency owner Christopher Draegert helped me in a very timely manner, called when he said he would, and took the time to explain all sections of the policies (coverage, limitations, etc) and answered all my questions. He helped me increase my liability limits while saving me money. I will definitely recommend him to friends and family.

Holly T., 7/31/2024 4:38:00 PM

Exceptional service and great policy options at affordable costs!

Alexandra R., 7/31/2024 4:33:02 PM

James was excellent. I would highly recommend James to everyone but especially to any first-time homebuyer. James was informative and clear as we were discussing coverage options. James also went above and beyond to accommodate my unusual schedule.

Crystal S., 7/23/2024 4:54:30 PM

Professional and knowledgeable!

Benjamin P., 7/18/2024 4:49:16 PM

Christopher has been a great help in this process.

Todd S., 7/16/2024 5:15:42 PM

Chris seemed extremely knowledgeable, and willing to explain anything that we did not understand. He gave us real-life examples of situations that helped explain coverages.

Elizabeth R., 6/25/2024 6:05:27 PM

James was incredibly helpful explaining all details of the policy and was very honest and up front about recommending the best option at the best price!

Amy S., 6/24/2024 2:07:34 AM

Christopher was very helpful and thorough in helping us to find car insurance for both of our vehicles at a very cost effective rate. We are on a tight budget, but also want to know we are covered well in any case. Christopher has a wealth of knowledge and got back to us in a very timely way. It was such an easy process and transition. Thank you!!

Onkarjot G., 6/13/2024 8:21:42 PM

Chris is very knowledgeable and was great to work with.

Catlin P., 6/13/2024 4:37:59 PM

Christopher was extremely helpful and made it a breeze to get through!

Monica B., 6/11/2024 6:18:06 PM

The communication and explanations were wonderful and at no point did I feel embarrassed or uneasy.

David T., 6/1/2024 7:21:24 PM

Very polite and eagerness to help, answered all my questions and a feeling of true caring in help me with the best policies

Karen A., 5/25/2024 4:23:09 PM

Very nice and very professional

Samuel C., 5/24/2024 4:43:56 PM

Christopher and James are great!

Sandra S., 5/16/2024 6:23:04 PM

Good communication and comment.

Kimberly N., 5/12/2024 8:34:30 PM

James was easy to work with and explained all of our options to us very clearly. We were able to save a sizable amount of money while keeping the same coverage.

Jacob C., 5/2/2024 2:02:45 PM

Christopher was wonderful throughout the entire process, what you want out of an insurance broker is a true “nerd” about it and from someone who is a nerd about payroll and taxes myself, I can recognize his passion clearly!

Jincy J., 4/25/2024 4:20:35 PM

It’s vey comfortable and useful

Trevor S., 4/24/2024 7:47:31 PM

Customer service

Taylor J., 4/16/2024 4:56:01 PM

James has Incredible communication and a clear passion for insurance! Extremely helpful and was able to find the best policy with a great price for us! Would recommend 10/10

Timothy H., 4/14/2024 11:57:10 PM

Chris was friendly, very responsive, and found us a great deal!

Barry C., 4/7/2024 1:53:13 PM

Christopher explained things with great details. He managed to get me more insurance coverage and renters insurance at a rate lower than my current insurance.

Kelly P., 4/1/2024 4:58:34 PM

Christopher called me on Easter morning to help get my policy set up to start the next day. He was super helpful, informative, and very professional and personable.

Ryan R., 3/28/2024 4:43:38 PM

Honest and straightforward!

Megan P., 3/21/2024 11:52:13 PM

Helpful, informative and knowledgeable

Janet L., 3/17/2024 2:22:11 PM

Christopher is easy to work with. He is very knowledgeable about all the products out there and what best fits for us.

Dorene S., 3/16/2024 5:22:41 PM

Excellent ang highly knowledgeable with a focus on customer service

Keith B., 2/24/2024 4:13:19 PM

Chris Dragert is a guy that I will recommend anyone who needs insurance. I don't say that lightly. He helped me get what I wanted it's such a reasonable price. You are so lucky to have a person like him to work for you.

Nestor V., 2/10/2024 11:19:01 PM

Very happy with the service, I wasn’t expecting the agency fee.

Peggy A., 2/10/2024 4:32:40 PM

James explained every thing and answered all my questions.

Sean H., 2/8/2024 4:16:33 PM

Christopher gives great service!

Shon P., 1/31/2024 4:32:15 PM

Chris is the best he was my agent for years in the past happy I to be back with him

Glenn B., 1/17/2024 1:40:27 AM

I was very impressed with Mr. Underwood's insurance knowledge and professionalism.

Rebecca B., 1/16/2024 4:27:15 PM

We were given great service in our initial meeting, were quite satisfied with prices quoted, and look forward to a good rapport with the team going forward.

Kimberly L., 1/14/2024 4:18:00 PM

James was very friendly, very knowledgeable, and he gave a lot of advice that we've never gotten from any other agent.

Shanika S., 12/31/2023 7:48:08 PM

I received excellent customer service from Chris in addition to securing better coverage and saving money!

Elizabeth R., 12/25/2023 7:11:44 PM

Chris was wonderful to work with. He gave us all the information we needed and asked about, and provided high quality customer service.

Gerald H., 12/7/2023 4:24:08 PM

Great service and knowledge and didnt stop till he found the best costs for my needs

Mary L., 12/6/2023 5:54:51 PM

Christopher Draegert was a pleasure to work with!

Cheryl J., 11/2/2023 5:28:37 PM

He made it fast and easy with great rates

Yvette M., 10/26/2023 10:40:04 PM

Chris explained the details of the policy, cost, recommendations etc., so I understood very well. I have already referred someone to him!

Dale S., 10/26/2023 5:43:32 PM

Excellent service and great products

Hannah D., 10/24/2023 4:57:18 PM

Very thorough and professional. Thank you!

Denise S., 10/23/2023 2:21:55 PM

Efficient service, friendly & knowledgeable agent

Abram D., 10/22/2023 2:03:29 AM

Personalized attention

Jessica S., 9/27/2023 7:02:27 PM

James is great!

Andrew C., 9/15/2023 4:50:44 PM

James was awesome. He was knowledgeable, informative, and sincere in his desire to get me and my family the best coverage possible. He is a fantastic representative of your company and has secured my business for all future needs. Thank you!

Rebecca P., 9/14/2023 5:18:58 PM

I had some frustrating experiences in the past, but James made the process easy and enjoyable. He was thorough and explained everything to me. I feel supported and well informed!

Eric H., 9/12/2023 11:05:42 PM

Knowledgeable

Koonal P., 8/25/2023 6:34:49 PM

Simply put - because of Christopher Draegert ! He was so personable and really took the time to explain things to me. I could tell that working with Christopher meant that I was forever now part of the flock, and that means we're protected and can go to sleep at night much easier. Thank you Christopher for all your help and assistance!

Thomas L., 8/14/2023 4:32:22 PM

Chris was knowledgeable and helpful, able to answer questions quickly and personably.

Katie L., 8/12/2023 10:53:33 PM

Seems very good. The rep was very knowledgeable

Jason C., 8/12/2023 4:50:33 PM

The process was easy and saved me a lot of money. James was helpful and did a great job of explaining everything.

Geraldine C., 8/9/2023 8:44:04 PM

Christopher Draegert was patient, thorough, very knowledgeable.

Mark S., 8/9/2023 5:13:07 PM

Excellent communication, fast response, all boxes checked on service and pricing. Thank you!

Tracy T., 8/8/2023 5:40:01 PM

Very knowledgeable and explained everything in detail instead of just saying this is what we quoted you and here’s your policy

Timothy R., 8/6/2023 4:21:01 PM

Great guys 👍

Steven Z., 6/5/2023 4:10:45 PM

James was incredibly easy to work with and is very good at explaining different things on both the auto and home insurance side of things.

Bridget O., 6/4/2023 6:31:55 PM

Chris Draegert is more excited and knowledgeable about insurance than anyone I have ever met! Glad to have someone like him helping us out.

Ardene K., 5/31/2023 3:54:50 PM

James Underwood was very thorough in researching insurance companies for me to consider. Also, he’s great with follow up.

Raymundo Z., 5/30/2023 9:32:37 PM

Great Customer experience and all the options really explained in detail. Thanks

Michael F., 5/30/2023 7:52:34 PM

Chris’s knowledge on the topic. Shortly into my first conversation with him I could tell he was a credible source of info.

Kane A., 5/30/2023 7:22:23 PM

James and Chris have been long time friends who I trust with not only my life but my insurance. They do not sugar coat what is or is not on policy and compare insurance to similar life experiences for the naive person who have yet to buy insurance. Ten out of ten use them.

Tonya S., 5/11/2023 4:29:23 PM

My representative, Christopher, was helpful beyond words. A first time home buyer, I was full of questions but didn't want to be overloaded with information that I wouldn't be able to process. Christopher was timely and crisp in his defining of my insurance needs and choices.

Elyse S., 5/2/2023 1:27:53 AM

Chris got me a great deal for both auto and homeowners insurance. He did all the leg work of calling the company's and working with my lender. Great experience!

Linda O., 4/26/2023 3:53:52 PM

Competitive rates, responsive, easy to work with, friendly

Patricia T., 4/26/2023 2:39:27 PM

Goosehead provided all the information for our insurance needs in Winthrop Harbor, IL. They provide all the information so we could make the best decisions for our new home.

Thomas L., 4/24/2023 9:13:13 PM

Chris explains everything very thorough and is a pleasure to talk with

John T., 4/24/2023 2:37:29 PM

Mr. Draegert is extremely knowledgeable. He makes complicated financial transactions easy to understand. He also has built a strong network. This allows his customers to talk to him to solve most financial transactions.

Shawn B., 4/16/2023 2:03:42 PM

The agent

Amybeth B., 4/16/2023 2:03:18 PM

The friendliest of the agent

Alec S., 4/12/2023 4:28:59 PM

Chris went above and beyond in helping us as first time home owners getting the best plans for us! Also, got our car insurance into a great rate with a complicated situation!

Brett B., 4/9/2023 4:42:53 PM

James Underwood was hands down the most helpful person I've ever delt with dealing with insurance. He took the time to thoroughly explain everything and even things after that I was unsure of he went into even more detail. I don't even personally know James but after talking on the phone with him and the way he treated me made it felt like I was dealing with a long time friend. I'm very happy I was able to stumble across Goosehead and even more greatful James was the one I spoke with. I'm sure this was a long term move for me as well. I thank you again for the smooth painless crossover. Sincerely, Brett Brenner.

Christine C., 4/3/2023 5:06:23 PM

Chris explained everything and helped me understand the process.

Austin G., 3/31/2023 4:48:28 PM

Christopher was amazing, very educational and super helpful.

Ana G., 3/29/2023 5:50:31 PM

Because Christopher knows about what he is presenting to you, which makes you confident about making the right choice. He will also always be looking for the best options not only making sure we have the best coverage but also a good deal as in terms price.

Heather R., 3/23/2023 1:29:35 AM

The process was smooth and easy. Everything was explained perfectly.

Daniel S., 3/17/2023 4:29:35 PM

Chris was very knowledgeable and provided prompt answers to my questions.

Jennifer L., 3/7/2023 5:19:51 PM

Christopher was very easy to work with. He made suggestions that work best for our family. Looking forward to continuing to work with him.

Dustin M., 3/3/2023 4:25:55 PM

Chris was extremely helpful and patient throughout the entire process! He explained everything about my current and new policy with me and talked me through each step! I would highly recommend him anytime!

Laura H., 3/3/2023 2:15:06 AM

Informative, clear and kind. And fast!

Kyle O., 2/28/2023 4:37:01 PM

Not only was James polite and positive but knowledgeable! He would have answers to my questions before I even asked them. 10/10!

Lori M., 2/27/2023 10:35:30 PM

Christopher Draegert was amazing! Fast and very detailed. And the price could not be beat. Trust me, I shopped around.

Amy H., 2/17/2023 1:57:31 AM

James was great!

Adam H., 2/17/2023 1:57:05 AM

James was fantastic! He not only helped me save some money on my policies but took the time to go over every coverage type that made sense for me and my family.

Maribeth W., 2/16/2023 7:11:16 PM

James was very helpful in finding me a better rate. Very knowledgeable about insurance

Steven L., 2/14/2023 5:45:06 PM

Chris really knew his insurance- better coverage less money and love covered for 12 months.

Christine M., 2/13/2023 2:30:46 AM

Throughly explained all aspects of the policy. Able to answer all my questions and concerns. Wonderful personality.

Maria S., 2/12/2023 5:58:38 PM

very good customer service

Eden M., 2/12/2023 4:14:42 PM

It was a pleasure talking to Christopher for 2 reasons....very competitive rates, but moreover honesty and simplicity going to every detail of insurance. Definitely I'll call him again.

Kelan S., 2/3/2023 1:22:15 AM

James was very knowledgeable and enthusiastic throughout the whole process.

Paul D., 2/2/2023 2:28:47 PM

Excellent customer service and knowledgeable in their field, would highly recommend.

Manus R., 2/2/2023 2:26:32 AM

Very helpful, saved me lots of money

Pawan K., 2/1/2023 4:34:46 PM

Excellent Advise on Insurance selection and reasoning behind it by providing competetive pricing.

Kerry A., 1/25/2023 4:29:43 PM

James, you were awesome and thanks for all the help and taking the time! Kate will be calling you when she is ready.

Courtney B., 1/7/2023 4:25:16 PM

Jack H., 1/1/2023 8:24:17 PM

I was able to get better homeowners coverage for the same amount of money and save on my auto. Chris did a great job and was very informative.

Nicholas N., 12/28/2022 6:30:08 PM

Christopher is a fantastic agent. Incredibly knowledgeable and enthusiastic about insurance. He knows his stuff.

Kelly A., 12/27/2022 5:19:15 PM

Christopher easily is the best insurance agent I have ever had. He researches, listens very well, and customizes insurance to needs. This is no "one size fits all," this is a great human taking time to listen and help. I will readily refer him, as I know he will take great care of whoever I do refer, and they will get great insurance based on their specific needs!

Gregory A., 12/14/2022 6:00:10 PM

Chris was wonderful, spending time actually analyzing our needs and presenting in a way that we felt he was looking out for our best interests in every way.

Jodeen G., 12/11/2022 1:27:05 PM

James was friendly and helpful. I will recommend

Irmgard K., 12/10/2022 4:59:00 PM

Christopher is really easy to work with and knows a lot about insurance. I appreciate him taking the time to go through the policy and coverage with me. Highly recommended!

Adam J., 11/29/2022 5:54:48 PM

This company is great and Christopher is awesome.

Jordan Z., 11/29/2022 5:53:45 PM

It was very easy to get switched over and I feel Christopher hit the ground running with all our needs! We are sort of a special difficult situation and he handled it quickly and effortlessly. I look forward to never having to deal with anyone again and we have found our forever company!

Jason R., 11/12/2022 4:48:48 PM

Customer service

Salina S., 11/10/2022 8:32:24 PM

I've never sat down with anyone who is as knowledgeable and thorough about insurance as we are.

Salvador S., 10/22/2022 1:14:46 PM

I know, Chris for a long time and he is a very good person. If you want honesty and good services Chris is the best.

Shammara E., 10/19/2022 1:24:55 PM

Good service and communication, patience....

Cynthia F., 10/6/2022 4:06:44 PM

James was very helpful &knowledgeable. He made the process go very smoothly.

Kamil A., 9/19/2022 6:26:14 PM

James is an amazing person. The best to talk to and is the most likeable and personable agent. He’s the reason I switched over. Best agent in the world! 007 nah it’s 00J

Kamil A., 9/19/2022 1:26:14 PM

James is an amazing person. The best to talk to and is the most likeable and personable agent. Heâ€™s the reason I switched over. Best agent in the world! 007 nah itâ€™s 00J

Tiffany F., 9/15/2022 12:00:22 PM

Very through!

Alvertis F., 9/13/2022 1:39:34 PM

Grade A customer service!

Harmony C., 9/12/2022 10:08:31 AM

James has been more than accommodating. He has explained everything in detail and has met all the insurance needs we had. He has been available when we needed him. I look forward to continuing working with goosehead for my insurance needs.

Benjamin L., 9/1/2022 3:52:11 PM

James was GREAT to work with and you can tell he loves his job. Thank you!

John S., 8/28/2022 8:05:40 PM

Christopher Draegert's customer service skills and sincerity.

Sarah B., 7/29/2022 11:14:35 AM

Very friendly, helpful, and personable

June M., 7/9/2022 8:49:29 PM

Helpfulness of agent!

Jordan A., 6/20/2022 9:22:01 AM

James was excellent and really helped me understand my coverage and the value it provides.

Kristin K., 6/19/2022 11:24:49 AM

Great service!!

Felix B., 6/1/2022 10:07:13 PM

Very professional

Danielle B., 5/22/2022 11:18:43 AM

James went above and beyond to not only get me a better rate and coverage but also thoroughly explaining the ins and outs of policy coverage. I will recommend James and Goosehead for all insurance needs moving forward. Thanks for all your hard work!

Eric J., 5/20/2022 10:04:04 AM

Christopher Draegert was exceptionally knowledgable and very friendly.

Kelly C., 5/15/2022 11:08:15 AM

Chris was great

Mark B., 5/13/2022 11:14:52 AM

Christopher was great. Made everything easy to understand and make the whole process simple.

Alexis O., 5/11/2022 10:43:43 PM

James was very helpful and informative every step of the way. He was there to answer every question I had and was very knowledgeable. Also I appreciated his thoroughness in figuring out which home insurance plan would work best for my family and I. James made the home buying process less painful and I appreciate all of his help!

Sean D., 5/10/2022 12:58:56 PM

Chris was top notch, knowledgeable and followed through with exactly what he said he'd do.

Christian D., 4/17/2022 7:01:42 AM

James was great, very helpful and he saved me money!

Christopher D., 4/6/2022 11:21:05 AM

Super detail oriented, covered all bases

Julie U., 3/21/2022 3:45:17 PM

James was very knowledgeable and he helped me with my insurance needs while saving me money and getting me even better coverage than what I had before. 5 stars!!!

Karen A., 3/18/2022 3:25:09 PM

James was very helpful, explained the coverage options so I could make the best choice. He is very knowledgeable and went above and beyond to make sure he educated me and that I understood everything I had available to me.

Amanda R., 3/15/2022 8:41:36 AM

Friendly and honest service. James is great at laying out all the pros and cons and walking you through the what ifs. It doesn't get better than that!

James A., 3/14/2022 1:25:18 PM

James gave great service, helped me obtain an Umbrella policy,l and Flood insurance!

James A., 3/14/2022 1:24:12 PM

James gave great service, helped me obtain an Umbrella policy, and Flood insurance!

Christopher D., 3/12/2022 10:50:32 AM

Christopher is amazing, super knowledgeable, and helpful. Was able to show me the value of an Umbrella, and flood insurance. I like knowing I'll have coverage if I need it!

Barbara D., 3/10/2022 12:03:43 PM

Knowledgeable about product, friendly and courteous

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