Insurance agency’s been growing for 37 years.

The personal touch is alive and well at the Killingsworth Agency. While television and radio tempt customers to buy online, Killingsworth’s 30-plus employees say their expertise and customer relationships make it worthwhile to get a comprehensive insurance picture from a live agent who has a customer’s best interests at heart.

Internet fans can do business or request online quotes from Killingsworth for auto, commercial auto, general liability, homeowner, homeowner flood, manufactured home, motorcycle, recreational vehicle, renters, truck, watercraft and wind.

They’ll also work with customers over the phone.

Owner and president Dianne Killingsworth Waldron professes a 37-year passion for insurance. The key to her success never changes: “You treat people the way you’d want to be treated; you care. Our customers are never going to complain that someone didn’t take the time to treat them right.”

Brooksville native Waldron didn’t plan a career in insurance. She needed a job and found one at a local insurance firm. She opened her own agency on January 7, 1974.

“It was just me, $150 and a lot of ambition,” Waldron smiled.

She rented a tiny 12 by 16 foot space in uptown Brooksville without plumbing or air conditioning. “The desks sat on Coke crates,” she reminisced, “Yet people came and bought insurance.”

Six months later she hired an assistant. They had two chairs that swiveled so customers could face either desk. Sometimes people sat on the steps waiting for quotes.

Nine months later Waldron bought the former “Orange Mart” fruit market on South Broad Street. Again, no air conditioning. “I didn’t have the money,” she recalled. “I just knew I had to buy that building. People sat in cars with the air conditioning on, waiting for quotes. It was so hot. People dealt with us in spite of it, because we did a good job is all I can figure.”

She purchased the Killingsworth (Candlelight) Plaza April 1, 1997, and built the Spring Hill branch about 10 years later.

According to Waldron, her three daughters – Lori, Lisa and Leah – are “all insurance people. They’ve all worked for me and have input into the family business.”

Waldron is especially proud of her four grandchildren. She tries to make life a little easier so her daughters can spend more time with their children. “I didn’t have that choice. I had to work and raise three little babies,” she added.

Being an independent agency, Killingsworth has relationships with dozens of insurance companies, which Waldron said lets them find the best options for customers with virtually any type of history.

There have been many opportunities to help customers throughout the decades. “From people with losses,” Waldron said, “to just being able to help people understand the insurance business, to show them what they need and keep their rates down.

“We give advice as a plan, not a momentary fix. A cheap quote may not really be the right thing. Many find that out when it’s too late. People need to know they can have a good agent and still save money.”

Most Killingsworth employees have been with the agency for years, many right out of high school. Some left to pursue college, marriage or other pursuits, and later returned. There’s even one mother-daughter team.

“A lot of my employees had no experience,” Waldron said. “Like me, they just needed a job. We help our agents with training and have high standards.”

Brooksville office manager Danielle Healis explained all agents are required to have a “4-40″ customer service license. The agency encourages and pays for expansion to a “2-20″ property and casualty license. Healis said all but a handful of their agents are 4-40s.

Healis loves the challenge of everyday changes dealing with insurance, adding, “Dianne is very good with her employees, promoting from within, working to develop your full potential. I’ve been here 22 years because we push building relationships with our clients, but more because of my relationship with Dianne.”

“She’s my right hand in Brooksville,” Waldron stated.

Spring Hill manager Karen Mack has been with Killingsworth 26 years. She remembers Waldron pulling up orange crates for clients in their “Orange Mart” location: “Everything was manual. We looked up policies on microfiche. We typed bills in 3-parts; yellow copies went into our desktop calendars. You should have seen them.”

Healis demonstrated how through their now-paperless system they pull insurance company data into their proprietary information without having to print.

Mack has managed Spring Hill since about 1988. She said Waldron is wonderful, the agency’s like family, and the office is her second home.

She advocates one-on-one customer relationships, explaining, “Customers should see the face of someone selling something like insurance. Our instantaneous access to motor vehicle reports and other information lets clients know immediately what they’re going to pay.”

The agency is big on community support. Healis is on the board of Operation HeartFELT (Feeding Empty Little Tummies), feeding homeless or displaced Hernando County children.

Waldron has been active with the Hernando Builder’s Association since 1979, and says the outreach that evolves from that is amazing.

At least twice a month Killingsworth attends events throughout the county, offering information and giveaways. “Agents must represent Killingsworth at a minimum of four community functions yearly,” Healis said.

“It’s just been growth, growth, growth,” Waldron concluded. “Not that it’s easy, but if you work hard, care about people, and treat them like you want to be treated, that’s success.”

The Killingsworth Agency is open Monday through Friday 8:30 a.m. to 5:30 p.m.

Jody Bowes writes regularly for Hernando Today. She lives in Spring Hill and can be contacted at

Insurance agency’s been growing for 37 years.
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