Leading a Third-Generation Agency: 6 Questions with Dana Dattola

Award winners, Leadership, Small Commercial Lines, Talent and Culture, Technology

As a third-generation agency principal, Dana Dattola knows that she can’t settle for the status quo. In the midst of her transition to full ownership of Weaver & Associates (in 2025, she will purchase 100% of the agency from her parents), she has led the agency to embrace digital tools, create a video production studio, transition to remote work and more. All this helped Weaver win the 2021 Agent for the Future Award for Outstanding Large Agency.

We talked to Dattola about how she decided to take over the family business, her experience as a woman in commercial insurance sales, how her agency has handled remote work and more.

What drew you to the insurance world?

I grew up seeing my parents have a lot of flexibility. We were able to go on a lot of vacations. We had a good lifestyle. They were always at my events and all the things for school. I went to college not knowing I was going to come back to the agency, but always having in the back of my head that it’s not a bad career path. I was thinking about maybe going into mortgage business, but I graduated in 2008 right when everything imploded, so I took a job at the agency. So I sort of fell into insurance, but I knew it was a good option.

Tell me a little bit about your experience as a woman in insurance.

If you go to any agency anywhere in the country, you’ll probably find that a majority of the account managers and servicing staff are female and the majority of the producers are male. That was how our agency was before I came in. My grandpa and my dad were the primary producers, with an office of 20 women servicing their accounts. There are a lot of women in insurance, but not a lot of women in production or leadership positions. I cannot think of one time in my career where the competition I’m going up against to earn an account is a woman.

There is a shift happening with business owners – most don’t see sex as much as previous generations. There’s less of the old boys club approach of having a three-martini lunch and writing an insurance policy on the back of a napkin. That does exist, and those accounts are hard to win over as a female. But overall, I’m finding it’s not super difficult to break through and get conversations started with business owners. But you do have to know your stuff. I think, as a female broker, you do have to prove you are smarter and more knowledgeable than your competition.

What do you like about being in insurance sales? 

I like to meet new people. I like to get out. I get that high from bringing on new business. Also, the beauty of sales in insurance is that you have limitless income potential. This is a really good business. It’s not a sexy business. Most people don’t think, “I want to be in insurance when I grow up!” But once you get in it, you have the flexibility and you also have endless opportunity.

I have some friends who are very high up in Fortune 500 companies. We went into careers at the same time, and at first, I was making commission only, while they were making more. But now they’ve kind of reached a cap, while with insurance, you can keep growing.

Flexibility has become even more important as the result of COVID-19. How is your agency handling remote work?

We give a lot of flexibility for our staff. Family comes first. As a mom, I get that. We’re not forcing anyone to come back to the office. We have a lot of employees who continue to work remote. I don’t really care if they are doing laundry or picking up kids, as long as they get their work done.  I do have a lot of male peers who are less apt to give that kind of flexibility. I meet with a lot of agency owners who say, “Oh no, we have to get them back in the office. They’re just sitting around at home.” But I trust my staff.

Now, I do think we are missing out on building company culture working remote. We do a big Brady Bunch Zoom call every morning at 8:30 with our entire team just to check in and say good morning. We’ve gotten good feedback from that, but we’re always playing with how to keep everybody connected when we’re not in person.

In your AFTF Award application, you talked about improvements in your agency’s technology. Why do you think it’s important for your agency to embrace digital?

It’s the future. My ideal client is like me: a business owner that is in growth mode. They want ease of use. They want quick responses. They want that personal customer service, but they also want things to be easy.

There are a lot of statistics about the third generation failing in businesses. My grandpa started the agency, and my parents were able to continue what he was doing. But when you get to the third generation, your consumers have changed. They have different needs. We need to stay relevant, because if we’re not growing, we’re dying. So that’s really the catalyst behind it.

What advice would you give other agents to be an Agent for the Future?

The hardest part is taking the first step in bettering yourself or your agency. It can feel overwhelming when you think about all that needs to be done, but don’t let that delay you from taking that first step.

Agent for the Future™ Staff

Agent for the Future exists to help independent insurance agents succeed. On AgentForTheFuture.com, we share insights from agents and industry experts.

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