The Middle Market Property Insurance Rollercoaster: How to Stay Steady in a Shifting Market

Akram Chauhan
7 min read80 views
The Middle Market Property Insurance Rollercoaster: How to Stay Steady in a Shifting Market

If you’ve been in the property insurance world for a while, you know the feeling. It’s like being on a rollercoaster. For years, we’ve been on that slow, clanking climb to the top—rates going up, capacity shrinking, and everyone holding their breath.

And now? It feels like we’ve just crested the peak and are starting to head down the other side.

After what felt like an eternity of rate hikes (seven straight years, to be exact), the market is finally shifting. Capital is flowing back in, and suddenly, there’s a whole lot more competition. This is great news in many ways, but it also brings a new kind of whiplash. How do you navigate a market that’s changing so quickly?

I recently got some great insights from Tom Krause, who leads Middle Market Property at Westfield Specialty, and he really put words to what a lot of us are feeling. “I would say rates are under pressure,” he told me. “If you look back about seven years, property rates have increased quarter over quarter. And there’s a point in time where the market pushes back on rate increases after 7 years of quarter over quarter increases.”

It seems we’ve hit that point. So, let’s break down what’s really going on and how you can find a steady hand to guide you through the ride.

So, Why the Sudden Change?

Remember the chaos after Hurricane Ian? It feels like yesterday. A lot of carriers got spooked, and frankly, who could blame them? Many pulled back, stopped writing property altogether, or seriously re-evaluated their books. Even huge players like some Lloyd’s markets hit the brakes for a bit.

That retreat created the tough market we’ve been living in. But in the background, those carriers were busy. They were reorganizing, adjusting their rate structures, and figuring out how to move forward.

Now, that capital is coming back with a vengeance. Tom mentioned that for many industry veterans, “2023 was probably the best property market that we have ever seen.” But that peak is over, and now “it’s retrenching and there’s pressure on rates.”

For carriers, this means it’s time to be smart. It's no longer about just riding the wave of rate increases. As Tom put it, “Now it’s up to us to go through our books of business, decide what types of accounts we want to keep, how we want to continue to diversify our portfolio, and at the end of the day, make profits for our organizations.”

This is where you start to see which carriers have a real strategy and which are just chasing the market.

The Often-Overlooked "Middle Market"

Let’s be honest, the middle market can sometimes feel like the middle child of the insurance world. It’s not the small, easy-to-place business, but it’s also not the massive, complex account that gets all the attention and resources.

This is exactly the space where a specialist approach can make a huge difference. Westfield Specialty has carved out a very specific niche here.

“We define middle market as any account with values of $100,000,000 or less,” Tom explained. But there’s a key detail: “The caveat is that our minimum TIV that we will accept has to be over $5,000,000.”

This positions them perfectly to serve those businesses that are too complex for a simple out-of-the-box solution but might get lost in the shuffle at a carrier focused on jumbo accounts.

How to Be Consistent and Flexible at the Same Time

In a market that’s constantly changing, you want a partner who isn’t changing their entire game plan every six months. It’s exhausting.

What’s interesting about Westfield Specialty’s approach is that their core appetite hasn’t really wavered since they launched their property division back in August 2021. “The appetite that we had then, we continue to have today with some minor tweaks,” Tom said.

But here’s the important part: those "tweaks" are all about flexibility. It’s not about changing what they want to write, but how they can write it.

“We have the ability now in our middle market portfolio to use different levers,” he noted. This is huge. It means they can get creative. They can offer:

  • Condensed primary coverage with smaller limits.
  • Quota share primary options (where they share the risk with another carrier).
  • Excess coverage capabilities.
  • Even full limits policies on certain accounts.

Think of it like having a whole toolkit instead of just a hammer. Whether a client needs an all-risk policy or just single-peril coverage for something specific, they can build a solution. “If you are a contracted producer with us,” Tom added, “there are very few scenarios with which we cannot help you, provided the request is reasonable.”

It All Starts with a Simple Conversation

Technology is great, but insurance is, and always will be, a people business. A good underwriter doesn't just look at the numbers on a page; they want to understand the story behind the risk.

Westfield’s process starts with five simple but powerful questions:

  1. What is it?
  2. Where is it?
  3. How was it built?
  4. When was it built?
  5. What is the catastrophe exposure?

“That right there tells us a good portion of the risk story,” Tom explained. But that’s just the opening line of the conversation.

From there, they want to know the context. “If you’re the broker, I would like to know if it’s your renewal or new business to you. Tell me what your challenges are,” he said. “Are there losses? Is your incumbent carrier giving you a hard time?”

This is what you get when you work with a team of seasoned pros. These aren't rookies learning the ropes; they’re people who’ve been on the retail side, the wholesale side, and even the reinsurance side. They’ve seen it all.

Using Tech to Power Human Connection (Not Replace It)

Okay, so they love to talk. But in today’s world, you also need to be fast. This is where a smart use of technology comes in.

Westfield has invested in tech that can essentially pre-underwrite a submission. “We have technology that can take the risk that brokers submit and triage it, if you will, on a scale of one through five,” Tom said. This immediately gives the underwriter a sense of whether it’s a perfect fit, a potential fit, or something outside their appetite.

But the tech does more than that. It cleanses the data and runs it through modeling before a human ever lays eyes on it.

The result? Speed.

“This helps us with speed to market,” Tom confirmed. “Now it gets to the point where, irrespective of what the effective date is, if it’s something that we really like, we can knock it out so much quicker than we could even a year ago.”

The beauty of this approach is that the technology handles the grunt work, freeing up the underwriters to do what they do best: talk to brokers and solve problems.

Just Pick Up the Phone

For all the talk of tech, the biggest takeaway for me was the relentless focus on personal communication.

“We have found…that what really makes a difference is our team using the phone and having thoughtful conversations,” Tom shared. “We like when a broker calls us and says, ‘I’m not really sure if this is a good fit, but what do you think about this?’ Those are the most fruitful conversations.”

It’s about being accessible. No hiding behind emails or portals. “Pretty much anybody that I deal with, they have my cell phone,” Tom noted. “We don’t like to hide behind the computer.”

In a market this fluid, that kind of access is invaluable. Having someone you can call or text when you’re in a pinch with a client can be the difference between winning a deal and losing it.

As we look ahead, the market will keep doing what it does: shifting. The key is to find partners who are built for the long haul. The ones who want to be there for you in the hard markets and the soft ones.

As Tom said, the ultimate goal is to “come up with creative solutions that they can take to the market.” And really, in this business, that’s what it’s all about.

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Risk Management Underwriting Market Volatility Insurance industry outlook Business Insurance Commercial property insurance Commercial insurance trends middle market property insurance property insurance market insurance market trends property insurance rates insurance capacity insurance market pressures insurance market shifts insurance carriers Westfield Specialty Tom Krause insurance competition insurance pricing insurance market conditions

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