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Insurance Strategies for Business Owners in a Bad Market

March 27th, 2025

3 min read

By Jerrett Phinney

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Insurance Strategies for Business Owners in a Bad Market
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You’ve got clients who haven’t filed a claim in five years. Yet, they’re still getting slapped with rate increases. You’re the one delivering the bad news every renewal, and frankly, it’s getting old.

The traditional market is unpredictable. Rate hikes often feel arbitrary. And when market cycles shift or carriers pull out of specific industries, your clients are the ones left holding the bag.

At Captive Coalition, we help independent agents bring solutions to clients who feel stuck. Whether it’s restructuring how they approach coverage or stepping into the captive space, we help agents move from reactive to strategic.

In this article, you’ll get a full breakdown of strategies your clients can use when the traditional market stops working, including what to do before, during, or instead of another renewal conversation.

Traditional Market Alternatives You Can Offer Your Clients

If your client is frustrated with the same broken renewal conversation, here are three alternatives within the traditional market that still give them more control—and give you something new to bring to the table:

Retrospective Rating Plans

These plans adjust the final premium based on actual claims performance. Your client pays an estimated amount upfront, and after the policy period, it’s reconciled:

  • Fewer claims? They pay less.

  • More claims? They owe more.

Retros are ideal for businesses with improving or stable risk profiles that want their insurance costs to reflect real-world performance.

High-Deductible Plans

For clients who are confident in their risk management, this structure shifts the “frequency layer” of claims to them. In return, they get lower premiums, but they may be asked to post collateral.

Some plans include aggregate deductibles to cap total out-of-pocket exposure, which makes the risk more manageable for clients who want upside without unlimited downside.

Self-Insured Retention (SIR)

With an SIR, your client pays claims directly up to a threshold. The carrier only steps in once that amount is hit.

The upside? Lower premiums. The trade-off? Your client must have the financial strength and discipline to manage those early claims efficiently.

Each of these strategies can help clients regain some control without abandoning the traditional market. As their agent, your job is to help them weigh the risk-to-reward ratio—and decide if it's worth it.

Can You Negotiate with the Current Carrier?

Sometimes. And it’s worth a shot, especially if your client doesn’t want to leave but needs a better deal.

Here’s how to position it:

“We want to stay with you, but this renewal doesn’t reflect how well we’re managing risk. We’re looking at other options, but we’d rather make this work. Is there anything that can be done?”

It’s a subtle power move that tells the carrier two things:

  1. You’re loyal, but not blindly.

  2. You’re watching the market and willing to act.

However, if your client has no intent to move, and you’re submitting applications year after year just to “check the box,” carriers will catch on. And eventually stop playing ball.

The Industry’s Dirty Secret: Why It’s So Hard to Shop the Market

You might already know this, but your client probably doesn’t:

Only one broker can represent them to each carrier at a time.

That means when large brokerages flood the market with submissions, they block other agents, or “block the market,” from getting quotes, even if your client wants a second opinion.

They’re not trying to win your client’s business by being better. They’re just making it harder for anyone else to compete.

Carriers hate this, too. Underwriters get burned out reviewing the same account six times, knowing it’s not going anywhere.

And if your client renews year after year without moving, underwriters stop taking their file seriously, especially with 1/1 renewals when everyone’s swamped.

This is why clients who think they’re “shopping the market” every year often aren’t. They’re trapped and don’t even know it.

Have You Talked to Your Client About Captives?

If your client is tired of feeling powerless in the traditional market, it’s time to introduce a model that works in their favor.

Captive insurance flips the script:

  • They take on more risk

    But it’s risk they’re already managing well.

  • They gain control over premiums

    Renewal pricing reflects their loss history—not everyone else’s.

  • They profit from performance

    Fewer claims = retained underwriting profit.

And here’s the kicker: captives don’t care what the traditional market is doing. No market cycles. No underwriting fatigue. No mystery at renewal.

It’s not for everyone, but if your client is entrepreneurial, financially stable, and already using high deductibles, SIR, or retro plans, they’re closer to captive-ready than they think.

Help Your Clients Take Control of Their Insurance

The traditional market is unpredictable. Whether your client stays in the system or steps outside of it, you can expose them to structures that reward how they actually run their business. Bring options other than “renew and repeat.”

Start with these articles:

Want to learn more about captives? Become a member of Captive Coalition for FREE to access additional resources, tools, webinars, and training to better help your clients and maintain your book of business.