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Reading time: 5 minutes

Welcome to the Pride,

Emerging risks. Evolving policy language. And losses that now regularly cross eight figures.

This is not a job for generalists—it's a domain for brokers who advocate like litigators and operate like boardroom strategists.

Here’s why this report is worth five minutes of your time:

1. It breaks down the exact pre-loss infrastructure and post-loss tactics elite brokers use to protect high-stakes clients when the pressure’s on.
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2. It reveals how carrier relationships, not just policy forms, determine your success when a claim hits, and how top brokers build real leverage behind the scenes.
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3. It shows how advanced tech—AI, analytics, and digital platforms—is transforming claims advocacy from reactive paperwork to proactive strategy.

But first, let's define what real claims advocacy means...

The LION POV: What Claims Advocacy Really Means

Claims advocacy isn’t paperwork.
It’s art. It’s war. And peace.

It’s your broker fighting like a trial lawyer when a carrier delays, denies, or lowballs a legitimate claim.

It’s someone who knows policy language better than the carrier’s own counsel.

It’s the difference between a seven-figure shortfall—and a full recovery.

Most brokers treat claims like customer service tickets.
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Submit the notice. Wait for the adjuster. Accept the offer. Hope you don’t ask tough questions.

The best claims advocates operate like outside counsel—only they know insurance law, carrier psychology, and how to flip a denial into a recovery.

The Hedge Fund Claims Story

Flip learned this the hard way.

Second year as a broker. Hedge fund client.

A routine SEC document request spirals into a full investigation—and then a lawsuit.

The firm’s leadership is buried in legal briefs. Partners should be managing portfolios. Instead, they’re managing panic.

That’s when the real value of insurance became clear.
Not just coverage.
But coverage that actually works when everything goes sideways.

Competent defense counsel. Backstopped negotiations. A client able to focus on business while experts managed the crisis.

But Flip never forgot the core lesson…

The carrier you choose matters more than the form you buy.

Why Choosing the Right Carrier Is Everything

A bank client came to us after being told $55 million was the max recovery on a claim.

We weren’t satisfied.

Two months later, we negotiated an additional $15 million. Same claim. Same facts. Different broker.

That $15M didn’t come from better paperwork. It came from carrier trust, built over time.

Some carriers see claims as problems to minimize. Others see them as promises to fulfill.

Choose wrong, and you’re fighting two battles:
One against the plaintiff—and one against your own insurer.

We’ve seen towers implode from the inside. Carriers pointing fingers. Legal fees stacking. Bad faith claims flying. $50,000/month in coverage counsel—just to argue about who pays first.

That’s not insurance.
That’s institutional malpractice.

Elite brokers prevent this by selecting carriers based on claims philosophy, not just premium.

They know who has authority to settle without seven committee approvals.
Who leads with partnership—and who lawyers up on Day One.

The Claims Intelligence Test

“Can you name three real claims where each of our carriers showed their true colors?”

If your broker cites marketing decks instead of war stories, you have your answer.

The Pre-Loss Infrastructure Elite Brokers Build

The real battle is won or lost before claims are ever filled.

Elite brokers build infrastructure before disasters strike. They build the system in advance.

They maintain relationships with claims teams who understand complex financial institution exposures. They conduct quarterly meetings to review your specific risks. They create notification protocols that work at 2 AM on Saturday.

Most importantly, they understand that the first 72 hours determine whether you're looking at a $5 million settlement or a $50 million verdict.

Especially in cyber, every hour matters.

When ransomware hits, you need forensic teams on the ground.
PR controlling the narrative. Regulatory counsel handling 50 states of red tape.

Elite brokers don’t scramble. They execute.

Infrastructure Test:

• Who are our claims reps, by line of coverage?
• When did we last meet about our claims response playbook?
• Can our plan activate in under 2 hours?

If they're scrambling for answers, you'll be scrambling when claims hit.

When AI Transforms Claims from Reactive to Predictive

The specialty insurance market will hit $279 billion by 2031, growing at 10.6% annually (source). One in five specialty policies results in a claim. (source)

That’s not chance. That’s certainty in disguise.

Which is why elite brokers have weaponized the same technology that's revolutionizing risk: artificial intelligence and predictive analytics.

Machine learning algorithms now predict claim outcomes with superhuman accuracy. They identify optimal settlement windows. They flag coverage issues before they become disputes.

But tech without strategy? Just expensive software.

Or as we say:
​“Giving AI to the wrong broker is like giving night vision to someone who’s never fired a shot.”

The elite use digital portals for real-time tracking—and combine it with human judgment forged from 100+ war stories.

They understand rocket docket jurisdictions.
They coordinate between defense and coverage counsel.

They know when to fight—and when fighting loses value.

If they’re managing claims through email chains and Excel?
You’re already behind.
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LION Specialty has built the industry's first AI-driven bad faith loss model specifically for insurance companies. We've compiled over 20 years of bad faith loss data, carrier behavior and decoded the patterns behind delays, denials, and underpayments. Using this data, we can forecast your institution's potential bad faith claim frequency and severity before the next loss hits. If you're interested in modeling your program’s exposure, contact us here.

The LION Lens

Your insurance program isn't tested when you buy it. It's tested when you need it.

The difference between elite claims advocacy and standard service can be measured in eight figures.

Material claims over $10 million have jumped from 8% to 19%.When that moment arrives, the quality of your broker determines one thing:

Whether you're explaining a managed outcome to your board…
Or a preventable disaster.

And none of it matters if you’ve chosen the wrong carrier.

Because even the best broker, the broadest form, and the highest limits can't overcome a partner who treats claims like liabilities instead of promises.

Your Six-Point Broker Audit:

1. Do we have pre-identified experts for each exposure?
2. Can you walk us through each carrier’s claims philosophy—with real examples?
3. Do you offer real-time tracking and predictive analytics?
4. Have you orchestrated complex defense strategies?
5. What recoveries have you secured on similar claims?

If the answers are vague, defensive, or MIA—you already know.

Because when the claim hits, there’s no trophy for second place.

Just settlements left on the table—and explanations owed to your board.

For more insights on protecting your institution, see our analysis of the one insurance mistake that could cost your financial institution millions and our detailed breakdown of recovering $250M in claims for clients.

The Bottom Line

If this all feels overwhelming—we get it. That’s why we’re here as guides and advocates.

Not just to sell policies.
But to build real protection.

If you're unsure about your current claims readiness, let’s talk.

We’ll review your carrier lineup, audit your claims playbook, and give you an honest read on where you stand.

If you’re a director or officer, your personal assets are in the blast zone.

That’s why we created the D&O Contract Vigilance Blueprint—a free 5-day email course that helps you:

• Secure better D&O coverage
• Spot overlooked gaps
• Protect your personal and institutional assets

​>>> Get the D&O Contract Vigilance Blueprint​

Don't wait until a catastrophic claim hits to find out your institution is under-protected.

Thank you for reading today's edition!

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Simply copy-and-paste the link below:
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Stay Covered,

Natasha & Mark “FLIP”
​Co-Founders
LION Specialty

P.S. Most directors don’t look at their carrier lineup until after a claim hits. By then, it’s too late. Let’s change that.