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The Problems We Solve

The CFO seemed confident when he called. Solid midwest dude. Strong operator.

"Our renewal is in good hands," he told us. "We've had the same agent for fifteen years. Great relationship."

That agent was their largest producer—their most trusted partner. Letting him handle the corporate D&O placement felt natural. Comfortable.

When we ran our standard review, we found twelve significant coverage gaps. Fraud exclusions that could have gutted a claim. Allocation language so vague it was a carrier gift. Notice provisions that were a trap waiting to spring.

None of it was intentional. It was just what happens when a "comfortable relationship" substitutes for systematic process.

How do we know this pattern? Because we see it every month.

Regional and mutual insurers, MGAs, and mid-market financial institutions operate at a structural disadvantage when it comes to insurance.

You're expected to make board-level risk decisions without the infrastructure, data, or market leverage the largest firms take for granted. The complexity of your exposures rivals that of much larger institutions—regulatory risk, fiduciary obligations, cyber exposure, directors and officers liability, but the resources available to manage those exposures don't scale down proportionally.

The gap isn't your fault. It's structural. And it shows up in three specific ways: limited access to expertise and global markets, an intelligence deficit that leaves you guessing on major decisions, and a transactional broker relationship that creates risk instead of reducing it.

We built LION Specialty to close those gaps.

The Access Problem

Expert brokers often overlook mid-market financial institutions because smaller premiums don't generate enough commission to justify senior-level attention. The math is simple: a $2 million account pays a fraction of what a $20 million account pays, so the $20 million account gets the experienced team and the $2 million account gets whoever's available.

The result is predictable.

You're served by generalist brokers who lack direct relationships in the global specialty markets where the best capacity and terms originate. Your submissions get filtered through wholesalers or layers of corporate bureaucracy, narrowing your options and weakening your negotiating position. Carriers that would compete aggressively for your business through a direct relationship offer narrower terms through intermediary channels.

Meanwhile, your competitors in the Fortune 500 get senior partners, global market access, and carriers bidding against each other for their business. You get off-the-shelf coverage and a take-it-or-leave-it renewal.

We bypass that structure entirely. Our team has direct, senior-level relationships with decision-makers in London, Bermuda, and U.S. specialty markets. These relationships were built over two decades of renewals and claims recoveries. When we bring a submission to market, it goes directly to underwriters who know us, trust our risk assessment, and compete for the business.

You get the same global leverage typically reserved for the largest financial institutions. Your premium size doesn't determine your service level.

The Intelligence Problem

Many of you operate in an information vacuum when it comes to insurance decisions.

You rely on outdated benchmarking reports, anecdotal carrier commentary, or generic industry summaries written for institutions ten times your size. When your board asks whether you have the right limits, you don't have credible peer data to answer the question. When your CEO challenges the pricing, you don't have analytics to back up your position.

When market conditions shift mid-cycle, you find out at renewal, months after the information could have helped you.

The modeling tools, carrier evaluations, and decision-grade intelligence that larger institutions use to optimize their programs? Many mid-market executives don't even know these resources exist in the commercial market. They use sophisticated analytics to buy reinsurance but make primary coverage decisions on instinct and broker assurances.

We provide boardroom-grade analytics tailored to financial institutions. Our benchmarking platform compares limits, retentions, pricing, and structures across real peer programs—actual data from institutions like yours. We pair this with loss modeling, scenario analysis, and carrier performance evaluations based on how carriers actually behave during claims.

The result: you defend decisions to your board with data. You quantify trade-offs instead of guessing at them. You walk into renewals knowing what's achievable because you have current intelligence on pricing trends, capacity shifts, and carrier appetite.

The Process Problem

The typical broker relationship is transactional. Applications go out in the fall, quotes come back a few weeks later, you bind coverage, and you don't hear much until the cycle repeats next year.

There's no ongoing education on what your coverage actually does, even though everyone needs that refresher annually. No tabletop exercises preparing your team for how a claim unfolds. No methodical renewal strategy that starts early enough to fix problems before you're locked into them.

We've seen the consequences too many times. A prospect calls us ten days before renewal with a bad deal, no data to support their concerns, and no time to get back into the market. Their broker ran a transactional process, and now they're stuck with whatever's in front of them.

Our renewal process starts 150 days out and ends 30 days before expiration.

That timeline creates room to maneuver—room to negotiate, explore alternatives, and handle complexity without pressure. Every client receives annual stress testing that examines coverage against real-world loss scenarios. Ongoing education that keeps your team current on what your policies actually do. Claims preparedness exercises that ensure you know exactly what happens when something goes wrong. Consistent communication throughout the year so you're never wondering what your broker is doing on your behalf.

You're never surprised. Never rushed. Never making major decisions with incomplete information.

The Client Benefit

You deserve the same talent, access, and intelligence that Fortune 500 financial institutions receive.

The fact that your premiums are smaller doesn't mean your risks are simpler or your board's expectations are lower.

We solve for access, intelligence, and process—the three structural disadvantages that leave mid-market financial institutions exposed. When those gaps close, insurance transforms from an administrative burden into a strategic asset. Programs perform under stress. Boards get answers they can trust. And executives operate with confidence that their coverage will respond when everything depends on it.

Thank you for reading today's edition!

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Stay Covered,

TASH & FLIP