Scaling an Insurance Agency – Q&A with Hotaling Insurance

An Insurance Agency’s Unrelenting Pursuit of Growth

Buckle up – you’re in for a real treat today with this Q&A!

You’ll hear from Jason Cavallo from Hotaling Insurance on how he and his team are growing rapidly and continuing to serve their amazing customers. Jason shares some helpful insights that will be sure to help you and your own insurance agency get to that next level of growth.

Hotaling Insurance

OLI’s goal with every agency is to fuel growth by leveraging our entrepreneurial drive, insurance market influence, technology, and back office support systems. When working with Hotaling Insurance, our goal was the same.

Let’s hear from insurance agency COO and Producer, Jason Cavallo from Hotaling Insurance, on how he’s better positioned for growth because of our partnership and relationship.


Jason Hotaling of Hotaling Insurance

How did you get into insurance?

“An internship led to an offer and the rest is history. I wasn’t supposed to be ‘in’ insurance. It just happened.”

Tell us a little more about your agency. Do you write all lines of insurance? Have a niche? Future growth goals?

“No one thing or niche practice defines our organization. We are a full-service risk management family office. We have several practices and partner companies that complement our insurance client’s business needs. Our agency is all encompassing and yes, we write ‘all lines’ of insurance. The collective of intellectual capital throughout the organization is remarkable with our current team. We are very strong in construction, real estate, professional organizations, and hospitality. Our growth goals are that we want to do ‘more!’”

What were your primary considerations when deciding which aggregator to use?

“Number One: Do business with people you like, trust and can count on. That’s why I went to Heffernan first* and was led to OLI. When I learned about OLI, I quickly realized the searching can stop – OLI is for us. Michael Hotaling, our Director of Operations and I, worked closely to ensure the partner we chose could keep up with our growth. We continue to have 40%+ growth year over year and a great part of that growth has been the commitment from and support of OLI.”

How important was it for you to have binding authority with your carrier appointments? 

“This was the ‘second’’ paramount [consideration] for us – We needed access and the ability to communicate, effectuate change and negotiate with the carriers versus the traditional model of having that ‘third party’ between us and the carrier. That can be polarizing. We don’t feel that at all with OLI in fact, it’s empowering to know that OLI has our back when we need some additional support, but they are in no way in our way of growth.”

How does your OLI experience differ from other aggregator experiences? 

“When I joined Hotaling and was ultimately tasked with being Chief Operations Officer, the first thing my team and I did was examine every appointment and relationship for access that we had. The insurance aggregator I inherited was great at what they do for small regional firms, however, we had goals to be national and were well on our way already with our Miami office just being launched. They couldn’t keep up with our growth nor support the regional underwriting we needed [so] we mutually decided to part ways. Since we have parted ways, that side of our business (via OLI) has been meaningfully different.”

Your agency has been growing rapidly, what has the experience been like adding on new staff/producers?

“I feel like we are onboarding new folks every week – Monday starts. The rush is incredible, the energy is contagious, and we all beam with pride in the result of our unrelenting pursuits.”

Beyond market access, what additional support do you receive from OLI?

“[OLI has] been prodigious with onboarding our new employees with training/s within the OLI affiliate portal. Demonstrating how to use the direct-bind portal/data entry so Hotaling receives commissions properly for the OLI carriers we access and place business with. I am also told that you all often help with password access/resets (timely) to the OLI affiliate sites which is critical, where we are not admin but OLI is.”

How do you spend your free time outside of work?

“When we are not at work, we are working remotely with family, but my free time is spent with my wife and family either watching my sons play sports or relaxing poolside with my Frenchie (Astro, he’s awesome!) or we’re traveling somewhere new when we can. We also take the time to pay it forward as often as possible with several organizations which I am proud to say was one (of the many great) takeaway/s from my experience with Heffernan Insurance Brokers*.”

We’re out at karaoke – what is your go-to song to sing? 

“Depends what we’ve been imbibing on… While I don’t search for a karaoke bar, there have been times where we stumbled onto one and well, simply… New York State of Mind, Billy Joel. Unless of course it’s one of those “seedy” joints and then, easily, any Zac Brown Band song (not just Chicken Fried) LOL.”

Anything else you’d like to share about OLI or the partnership?

“We couldn’t be more appreciative of the partnership and we’re looking to be your most significant broker-partner so get ready!”

*Jason developed his insurance expertise while working as a producer at Heffernan Insurance Brokers, the parent company of OLI Insurance Services, Inc. 


As you could see from Jason’s story, Hotaling Insurance Services was in an interesting situation poised for growth. By working with us, we were able to provide Jason and the Hotaling team with the insurance aggregator support they needed to take their growth to the next level. Our tools and resources are carefully created for the insurance agencies who know they need help and are searching for answers. 

If you have any questions about our services, how we can help you, or if we can help you do what we did for Hotaling, please contact us to start the conversation.

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