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Meet Annmarie Westerfield


Annmarie Westerfield is the current COO for the Anthony S. Cupo Insurance Agency. She has enjoyed membership with Big I NJ for over 25 years and has served on the board of directors for the past two. 

Her insurance career started at the young age of just 14 where she used a typewriter at her part-time data entry job. Thankfully that didn’t thwart Annmarie from pursuing a lifelong career as an agent, despite it being her ‘until I’m a teacher’ job.

Why did you choose a career in insurance? What initially brought you to the industry?
When I was 14 years old my father said, “It would be a good idea for you to get your working papers and look for a part time job.” At the time our neighbor was a bookkeeper at a local independent agency and they were looking for a file clerk. (Side Note: this was 1981 so they still used typewriters!) I started working at the agency after school and over the summer all the way through college, quoting simple auto policies, typing applications, filing, answering the phone, and doing simple data entry. After college, I was looking for a teaching job during a time when the market didn’t have a lot of open teaching positions so I ended up taking a job at an agency “until I found a teaching job”.  They sent me for my license and the rest is history!   

How has being a member of the association impacted your career? 
I can’t imagine being in this industry without being a member of the Big I. Insurance is such a unique industry. We really need as many resources as possible to keep current on market trends, coverages, legislative matters, and insurance company ratings and offerings. When I have a question about anything pertaining to insurance in general, the first resource is always Big I NJ. That may be by attending an event, asking other members, or by visiting the website or Big I University. Big I NJ is one of the most valuable tools I have at my disposal and I would advise anyone thinking of joining to just do it!  The products are great and the staff is the best!

What do you see as the greatest opportunity for our industry over the next 5 years? 
We have an opportunity for the “passing of the torch”.  Agents preparing to leave the industry have so much knowledge and talent and it is our opportunity and obligation to pass that knowledge onto younger people in the industry so they can to take that experience and use it in new and different ways going forward.   

What technological breakthrough, device, or innovation, do you think will have the greatest impact on insurance over the next 5+ years? 
In my opinion, it is going to be AI. I confess that I don’t really know all of the ways it will change our business, but rest assured it will.  At a recent board meeting I saw first-hand how ChatGPT works and my jaw literally dropped at what it can do. It’s fascinating, but also a bit frightening!

What advice would you share with individuals just starting out in the industry?
Knowledge is power.  If you only learn about one type of insurance, or one job function, you will limit yourself. Take every opportunity to try new things, take new education courses, and attend industry functions (Big I NJ has great events!). Eventually you will settle into the role that suits you best, but if you can build a foundational knowledge about our industry, I promise, you will succeed.

What are you most looking forward to accomplishing during your time on the board?
I hope to help strengthen our program utilization for agents by getting the word out on what’s offered and how it will help agents. I would also like to focus on engagement and education for our members. There is so much available if you just know who to ask or where to look.  

What one hidden gem – as it relates to benefits/resources - do you think more Big I NJ members need to be taking advantage of? 
The Ideal Traits job searching tool, which is offered at a discount to members. You can advertise open positions and have it broadcast out to numerous job boards, access templates for job ads or assessments to send to applicants, and more.  It really makes a very challenging process of hiring much easier.

Who is your mentor?
My biggest professional mentor was my first boss, Dave Madden.  I worked at his agency for almost 20 years from high school through adulthood. He started as a one-man shop in his basement and grew to be a very successful Morris County agency. I learned so much from him - I don’t know that I will ever have another mentor like that.  

What is your greatest motivator?
My greatest motivator is being able to contribute in a meaningful way, no matter what I am involved in.  Financial reward is great, but I need to feel like I am a part of something, to be able to make a difference.   

What is the best professional advice you have received?
Don’t be afraid to take a chance.  Raise your hand and say “I will try it”. Don’t be afraid to fail.

What's something that most people are surprised to learn about you?
I have a great sense of humor and I love to laugh!