Randy Wentworth

  • Personal Lines & Claims Manager, Chalmers Insurance Group
  • 200xrandy-wentworth
InVEST Graduate Leverages Connections and Builds Successful Career

Randy originally wanted to enroll in nursing school, and he did just that after graduating in from Sacopee Valley High School in Maine. But he later realized that route wasn’t for him, and thought of a career option he learned about in high school.

Randy had participated in InVEST, a non-profit IIABA program that provides insurance education and career awareness to high school and college students.The InVEST program at his school provided an opportunity for students to run mock insurance agencies and later move to onsite work study with several agencies in nearby Portland, Maine.

While looking before college, he found a job with Commercial Union Insurance as a claims clerk.

“My intent was to keep the job just until the following semester, then go back to school,” Randy said. However, he quickly realized insurance was a great fit for his career goals and personality. From the start, he could go places in the company, felt challenged and enjoyed helping clients.

In 20 years, Randy started as a typist, became a claims processor, then a workers compensation adjuster, and eventually a senior property adjuster. He eventually became a personal lines underwriter for six years. During that time, he earned a business degree, taking two courses a semester.

Randy then hit another career milestone and was hired as an agency manager for the Chalmers Insurance Group. As a way of giving back, he and other Chalmers' employees reached out to several local high schools to establish InVEST programs.
“In my current position, I realized the importance of InVEST,” he said. “And Chalmers has other employees who are InVEST grads -- some of our best workers.”

InVEST continues to perpetuate the independent agency system. For more information, visit