Declaration of Independents: Todd Dailey

• By: Will Jones
• October 1, 2026

Todd Dailey

President, Chief Operating Officer

Insurance Management Group

Indianapolis, Indiana

Dailey’s approach to technology at Insurance Management Group follows a simple hierarchy: people, process, then technology. Guided by the belief that employees who are well supported deliver better client experiences, Dailey places more emphasis on process than technology to ensure employees have what they need to succeed.

“Those processes should be shaped by listening to the people doing the work, understanding what is already working well and learning from top performers,” he says.

“Technology should come last because it only magnifies the quality of the process underneath it,” Dailey adds. “If the process is poor, the technology can make the problem worse, but if the process is strong, technology can make it more effective.”

Keys to being a data-driven organization?

Making sure the data is clean enough to trust, building dashboards that are easy for people to understand and creating forums where leaders and teams can look at the information together. The data by itself is not enough.

Lessons from carrier background?

What gets measured gets managed. If you are looking at the right things and making the information visible to your team, it helps the organization understand where it is succeeding and where it needs to improve.

Adopting new technology and driving buy-in?

Start with the problem, not the technology. If you begin by saying, “Here is a shiny new tool,” people may not immediately see how it fits into their day. But if you start with the issues your team is experiencing, adoption feels very different.

After that, it helps to identify champions. These are the early adopters who are excited to experiment, test things and work through the kinks. Then you need to celebrate wins visibly. When other people see how the tool is helping a peer save time, solve a problem or serve a client better, they are more likely to lean in.

How do you share data with your team?

We sit down with team members and review the numbers together. We talk about expectations, goals, client experience and anything the data may be showing us. If a metric has dropped, we do not want the conversation to feel like, “You need to get this up.” We want it to be more collaborative: “What do you think happened? How can we help? How can we better support you?” That turns the numbers into a mutual conversation. It helps people feel like the data is there to support them and help them improve rather than to punish them.

What is Premium Logic?

Premium Logic came out of our own need inside the agency. When I came to Insurance Management Group in 2018, I was pulling massive reports out of our agency management system (AMS) and trying to get useful information from them. It was difficult to get the data I wanted in the way I wanted it. So we built a central intelligence system around the data and analytics we needed across the agency. It started as an internal tool. But as we worked with other agencies and shared best practices, we realized a lot of them had the same challenges. Some of those agencies asked whether we could build something similar for them, and that eventually became Premium Logic.

What do you love most about working for an independent agency?

I love being close to the customer. At an independent agency, you have proximity to the customer, can understand their needs and find creative ways to add value and serve the community. I also appreciate the people in this industry. The independent agency channel is relationship-first and hospitable, and I have really enjoyed working alongside those people.

Advice for an owner who is grappling with technology, artificial intelligence (AI) and data?

Start experimenting. With analytics, agencies often put dashboards in place, then discover data quality problems, which can reveal process issues that need to be fixed. You do not see those things until you start looking.

The same is true with AI: Test it thoughtfully, do not put client data into free tools and be comfortable working backward as the technology uncovers areas that need improvement. If you wait until every process is perfect and all the data is clean, you may never start.

How are you embracing AI?

Our approach has been experimental. We built a closed-loop system that connects to different AI models, and we have an enterprise-level subscription with Claude that a sample of our users can use. We are also experimenting with insurance-specific AI tools.

At the same time, we are trying to stay grounded in the basics. There is a lot of value in simple things like chat, spreadsheets, summarizing information and asking for clear explanations. If people use those capabilities consistently, there is a tremendous amount of value there.

Soft market strategy?

In a softening market, retention becomes even more important because new business can be tougher. But retention itself is a lagging metric, so we try to focus on the leading indicators that help drive retention. Are renewals getting out on time? Are we having midyear check-ins? Are we doing the things that lead to a client staying with us?

Measuring the client experience?

We use net promoter score (NPS), post-renewal feedback and simple ways for clients to tell us how things are going. That feedback helps us identify issues, but it also has a positive internal effect. When the team sees good feedback from clients, it reminds them that the work they are doing matters and that they are making a difference.

Will Jones is IA editor-in-chief.