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Chartwell Insurance Services




As our featured business for September, we interviewed Rebecca Woan, Founder and CEO of Chartwell Insurance Services. Read the full interview below!


S&S: When did Chartwell Insurance open? Tell us a little about the history of the company.

RW: Chartwell Insurance Services was my maternity project when my youngest was born. She is about to turn 17. I didn’t know anything about babies and thought I would be bored. Needless to say I was pretty busy but I did have a chance to put a business plan together. For some time before my daughter was born I was sure that individuals of emerging wealth and the affluent needed an insurance advocate who focused solely on the needs of those individuals, rather than as a sideline accommodation to commercial customers. Having some time off from work with the baby gave me the chance to put my thoughts together and create a business plan although not much else than that.


S&S: What different kinds of insurance options do you offer?

RW: We provide coverage options for homes, automobiles, collections, domestic workers compensation (especially important when employing nannies and house managers), family office coverages and non-profit directors and officers liability.


S&S: Tell us about the Chartwell Insurance team.

RW: The Chartwellians, as we call ourselves, are a group of individuals committed to assisting and educating our clients. We work together as a team which is very helpful to clients.


S&S: What qualities do you look for in an employee?

RW: Beyond experience either in arts or insurance, I like to see responsiveness and a sense of immediacy. Our clients expect answers immediately and it’s critical that we respond right away. If a job candidate doesn’t follow through promptly on an email exchange, is late for an appointment or changes an appointment I’m not inclined to reschedule. The ability to write is also important because so much of our communication is through email.


S&S: Any tips when shopping around for insurance options/companies?

RW: Most people don’t realize that there isn’t an advantage to have different brokers shop the program for you. Some markets will be locked after the first broker quotes.

We suggest that the process should be about broker selection. A good broker will present the options. What the client needs to do is to find the broker they believe is most capable of taking their program to market and of servicing the account. Ask the broker which companies they represent with direct contracts (as opposed to a wholesaler), You can verify this by checking on the company website under the “agent finder.” If you don’t find the agency listed they likely work through a wholesaler and don’t have a direct contract with the insurance company. This means they can’t negotiate directly with the underwriter.


S&S: Tell us about the process of purchasing insurance through Chartwell. Do you start this process in person or via your website?

RW: At Chartwell, we say “Start with a conversation not a click.” If you go to our website you can leave your contact information and we will call you.


S&S: Have you received any awards or accolades you would like to mention?

RW: I was named one of the top women in insurance by American Agent and Broker in 2013.


S&S: What sets Chartwell apart from other insurance agencies?

RW: We are a boutique agency specializing in property and casualty insurance for the affluent and high net worth individual. Our objective is to advocate for our clients. The highest compliment we receive comes from our clients who work for our insurers and want us to represent them because they know how persistent we are in pushing the underwriters to offer the best program for our clients. Also, we are involved in claim settlement. We don’t just tell our clients to call an 800 phone number. Instead we are available 24 hours a day for our clients who experience an emergency.


S&S: We know you are headquartered in Chicago. Do you only provide services to those local in Chicago? Or do you service clients nationally?

RW: While we are based here in Chicago we work with clients everywhere in the US, those who have homes overseas as well as foreign nationals working in the US.