There are two ways for Insurance Companies, Banks, Private Equity firms, MGAs, and insurtechs to approach complex risk in 2025:

1. Rely on generic solutions, potentially overlooking critical gaps.
2. Partner with specialized expertise that delivers clarity and tailored protection.

Many sit in the first category, often underserved by mega-brokers.

Your institution has unique strengths and ambitions. 

But is your risk management truly aligned? 

Or are you unknowingly exposed due to:

–  Coverage gaps hidden in the fine print?

–  Lack of access to sophisticated global markets?

–  Decisions made without credible peer data or advanced analytics?

–  Impersonal service that doesn’t grasp your specific operational realities?

The bigger problem?

You're leaving strategic advantage on the table and potentially facing significant financial or reputational risk down the line.

The solution?

Transform your risk management from a necessary cost center into a strategic asset through a bespoke, expert-driven partnership.

That’s my focus at LION Specialty.

My approach combines:

– Penetrating technical analysis honed by deep experience (including handling complex Fortune 100 accounts) to uncover what others miss.

– Global market access (London, Bermuda) and perspective, crafting solutions beyond standard domestic offerings.

– Process mastery & advanced analytics delivering clarity and confidence, not complexity.

– Authentic human connection, building partnerships that thrive.

(informed partly by my wellness background as a Pilates instructor… sustainable success requires balance)

–  Are you serious about closing critical coverage gaps?

–  Are you ready for risk management bespoke to your institution's needs?

–  Is it time for a partner who brings both sophisticated expertise and a refreshingly collaborative approach?

Let's connect and explore how we can elevate your strategy together.

Natasha Kiemnec

I was 24 years old, the youngest person in the room by at least 15 years.

And I was terrified of asking the wrong question.

The client was one of Aon's marquee accounts. The meeting was high-stakes. Everyone around the table had decades more experience than me.

So I stayed quiet.

I nodded along. I took notes. I tried to look like I belonged there.

But halfway through the conversation, something wasn't adding up.

The numbers the client was describing didn't match the risk exposure we'd outlined in the proposal. It seemed like a pretty basic disconnect, but no one was addressing it.

I figured I must be missing something obvious. These senior leaders would've caught it if it mattered, right?

But the gap kept nagging at me.

So I took a breath and asked what felt like the most obvious question in the world:

"Can we walk through how you're calculating exposure? Because I'm seeing a difference between what you're describing and what we've modeled."

The room went quiet.

Then the client looked at his CFO and said, "That's a good question. Can we?"

Turns out, they'd been using an outdated methodology. And no one on their team had flagged it because they all assumed someone else understood it.

My "obvious" question uncovered a $2M gap in their coverage.

That moment taught me something I still carry today:

Technical excellence doesn't come from pretending to know everything.

It comes from being curious enough to ask the questions everyone else is afraid to raise.

Now, when I'm mentoring the next generation of actuaries at LION, I tell them this:

The questions you're embarrassed to ask? Those are usually the ones the room needs to hear.

Because the most dangerous assumption in any technical field is that someone else has already figured it out.

Your lack of experience isn't a weakness. It's permission to question the status quo without ego getting in the way.

So ask the obvious questions. Challenge the assumptions. Speak up when the numbers don't add up.

That's how you build real expertise—not by faking confidence, but by staying relentlessly curious.

What's one question you've been afraid to ask in your work that might actually be worth raising?

Natasha I.  Kiemnec, ARM

Managing Partner & Co-founder of LION Specialty | Global Financial Institutions & Private Equity Broker | Classical Certified Pilates Instructor

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In my first broker role, I caught what 3 senior brokers missed in a major insurance program.
And there's such a simple reason why:

I actually read the policy.

All 200 pages.
Every endorsement. Every exclusion. Every definition. 

The senior brokers had reviewed the summary of coverage.

Confirmed the limits. 
Negotiated the premium. 
They'd been doing this longer than I'd been alive.

But on page 157, buried in a definition nobody checks, was language that invalidated coverage for the majority of the client's operations.

"Financial Interest" was defined to exclude any subsidiary with less than 50% ownership.

The insured had 47 subsidiaries. 31 were minority stakes.

Their biggest exposure - a 49% stake in an overseas operation - had zero coverage.

Massive uncovered liability. 
Exposed for years.

When I raised it in the meeting, the room went silent.

The senior brokers pulled up the policy. Read the definition. Re-read it. Called the carrier.

That's the unfortunate truth about coverage summaries.

Carriers write them. Carriers set what counts as "standard." And carriers count on brokers not reading page 157.

At LION, every team member - from associate broker to partner - reads every policy.

Not summaries. Not excerpts. Every single page.

Because experience without diligence is just confident ignorance.

And ignorance at page 157 can destroy everything.

~

Every Friday we share insights that cut through insurance complexity.
Comment 'brief' and I'll get you on the distribution!
LION Specialty 🦁

Legally, a drone is an aircraft.
That one definition nearly created a multi-million dollar uninsured loss.


I was reviewing a policy for an insurance carrier client.

We reached the "Aircraft and Operational Machinery" exclusion.

The CFO stopped me.
"Wait. We use drones to inspect property claims. If this exclusion stands, are we covered?"

Technically? No.

If the policy excludes "aircraft," and the FAA defines a drone as an "aircraft," the carrier can deny the claim.

Most brokers would wave this off.

"It’s a standard exclusion. They know what you do. It’ll be fine."

I don't rely on "fine." I rely on the contract.

We added a carve-back:
"This exclusion does not apply to the use of unmanned aircraft for claims handling and loss assessment."

One sentence.

Total protection.

Standard forms are written for hypothetical companies.

Manuscript policies are written for your operations.

How many "standard" exclusions in your policy are silently blocking your actual business operations?

Book a review. We usually find the first gap in 15 minutes.

A single word just split a federal court ruling.


Most financial institutions treat their Crime Bond and their Cyber Policy as two separate safety nets.
But a recent ruling (Hartford vs. HSB) just proved why that is a dangerous assumption.

The Bond was dismissed. The Cyber policy survived.
The difference wasn't the loss itself. It was the definition of "Causation."

Here is the nuance that most programs miss:

1. The Bond: Often excludes losses where an employee is "tricked" into sending money (Social Engineering). It requires the computer itself to be the cause.

2. The Cyber Policy: Applies a more permissive "direct result" standard that holds up even when human error is involved.

If you are relying on a $250k Social Engineering sublimit to cover a seven-figure wire fraud loss, you are exposed.

I’ve spent years architecting programs for financial institutions, and I always look for this specific friction point.

You cannot map these coverages in silos. They have to work together.

We broke down the full legal framework in this week’s Boardroom Briefing.

Comment "BRIEF" and I'll send it over.

Eighteen years in insurance taught me what no training manual covers.


Here are the unspoken rules that matter most:

1. Relationships outlast resumes.
The best placements don't come from knowing the product. They come from knowing the underwriter who can make an exception. Build the relationship before you need the favor.

2. Saying "No" is a skill.
Early in my career, I said yes to everything. I learned the hard way that overcommitment leads to mediocrity. Boundaries create the space for excellence.

3. Ask the "Junior" questions.
I was 24, manuscripting policies with General Counsels. I asked questions that probably annoyed them.
But asking when you don't understand builds expertise faster than pretending you do.

4. Own mistakes immediately.
Coverage errors happen. The brokers who survive own them fast. The ones who spiral try to hide them. (This one I learned early days from my parents.)

5. Physical discipline supports mental performance.
You cannot sustain high performance on declining physical capacity. Insurance rewards endurance. Train for it.

Nobody told me these rules at 22.
I learned them through trial, failure, and watching others burn out.

What has been the key to your most career success?

Ps. Also! Make the most of the travel, and make it fun.

Eight auto insurers paid New York $19 million for the same mistake.

Hackers stole driver's license numbers through their online quote tools. These were the same tools insurers use to capture new business.

Hartford paid $3 million. Liberty Mutual paid $2.7 million. Farmers paid $2.775 million plus extra penalties for not reporting on time.

These weren't sophisticated attacks. DFS warned about these exact vulnerabilities in 2021. Four years later, companies were still exposed.

The department has now collected $144 million in cybersecurity penalties across 27 entities.

The message is clear. If they found violations in your most basic public-facing application, what else are you missing?

And if you miss the 72-hour breach notification window, you pay twice. Farmers and Infinity learned that the hard way.

We break down regulatory signals like this every week. Comment NEWSLETTER for the link.

Your broker is either your greatest strategic asset...
...or the most expensive false sense of security you'll ever buy.
The difference comes down to three things: 

how deeply they know your world, whether their systems were built for it, and what happens when a claim hits.

A generalist broker works hard. 

They juggle manufacturing on Monday, healthcare on Tuesday, and your credit union on Wednesday. 

That effort is real. 
But effort and immersion are different animals.

After 15+ years serving only financial institutions, we've reviewed hundreds of FI programs. 

We've seen what breaks. 

We know that a mutual bank's volunteer board creates different D&O exposure than a community bank's paid directors. 

We recognize the regulatory triggers that turn routine exams into coverage events.

Pattern recognition compounds over decades. 

A generalist sees your program once a year. 

A specialist has seen your exact problem a hundred times—and remembers how it played out.

Financial institution risks don't behave like other industries. 

Your exposures intersect in ways that require fluency, not familiarity. 

Cyber meets professional liability. 
Regulatory action triggers D&O. 
Crime losses cascade into reputational damage.

A broker who doesn't live in this world can't see these connections coming.
Immersion determines whether your coverage works when everything depends on it.

🦁

Florida homeowners just got 8.7% rate cuts.
That's the headline. Here's what actually happened…

CFOs, CUOs, and board members at regional insurers, mutuals, and MGAs…

I've watched litigation costs shape premium volatility more than any catastrophe season. 

Florida used to account for 8% of national homeowners claims while generating nearly 80% of litigation costs.

After 2023 tort reforms, the state dropped from 2nd to 10th in national nuclear verdict rankings. 
Seventeen new carriers entered.
 Private capacity returned. 

Now rate relief is flowing across homeowners, auto, and commercial lines.

That's not just a Florida story. 

Seven states built the blueprint.

Meanwhile, financial services topped the 2025 breach list with 387 incidents in H1 alone. 

Experian predicts AI agents will overtake human error as the leading cause of breaches next year.

Two patterns converging. 

One board conversation.

We unpack all three developments in this week's Friday Five Boardroom Brief.

Read the full breakdown in this week's Boardroom Brief. Comment "BRIEF" below and I’ll get you on the distribution.

P.S. one of my favorite places to travel for work! does your job take you anywhere cool?

At the American Bankers Association Risk Management Conference in Orlando?

I’m on the Brightline Trains on my way up. 

Would love to meet up! Send me a note. 

(And yes, I changed my hair)

Twenty-seven reciprocals formed between 2017 and 2024.

Eighteen of them launched in just the past year. Premium volume grew 83% in two years.

Traditional carriers pulled out of Florida and other cat zones after massive losses. Reciprocals stepped in to fill the gap. They now bring $51 billion in premium capacity to the P&C market.

The sector runs in two tiers now. Established players like USAA, Farmers, and Erie have fortress balance sheets and decades of history. The newcomers bring innovation, but eight of them scored below 30 on ALIRT's financial strength scale.

AM Best called reciprocals a "compelling answer to market gaps." Policyholders control rates, strategy, and overhead. Insurer and insured interests align because they're the same party.

If you're a financial institution evaluating a reciprocal partnership, understand the model first. Surplus notes provide initial capital. Management fees fund operations. Subscriber control creates alignment.

DM me if you want to talk through how these structures actually work.

The difference between Lloyd's manuscript forms and domestic policies, explained 
(because insurance contracts are complicated and most people never see how they’re actually built):

Lloyd's is a marketplace of syndicates.

Each syndicate underwrites risk independently. And brokers with the right authority can draft custom manuscript forms specifically for their client's exposure.

But Lloyd's syndicates don't hand manuscript authority to just anyone.

You earn it.

How? Through decades of trading relationships. Clean claims reporting. A track record of accurate underwriting.

We earned ours over 20 years.

When does Lloyd's make sense?

3 situations where I recommend it:

• Complex FI risks that don't fit standard domestic forms  
• Need for affirmative coverage language (not just silence on coverage gaps)  
• Operations that span multiple coverage lines in ways domestic carriers won't touch

The structural difference is massive:

Domestic policy: 200+ pages of assembled forms, endorsements, and exclusions bolted together. 

You're hunting through layers to figure out what's actually covered.

Lloyd's manuscript: 40 pages. Custom-drafted for the specific risk. 

Everything in one place.

Clarity vs. ambiguity.

Lloyd's isn't always the answer.

For straightforward risks, domestic markets are faster and often more cost-effective.

But for certain FI risks - especially those with unique exposures or operations that don't fit the standard boxes - Lloyd's is the only option that makes sense.

Because you need coverage that actually responds when there's a claim. 

Not coverage that leaves you in a 3-year coverage dispute.

By the way…

Every week we share curated insights that cut through insurance chaos and help you make the best policy decisions.

Join here: https://lnkd.in/garzxSxG

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Classical Pilates Certification 

Associate in Risk Management - Enterprise Wide Risk Management (ARM-P)

Advanced Open Water Scuba Diver

Co-Founder & Managing Partner

NFP is a leading insurance broker and consultant that provides employee benefits, property & casualty, retirement, and individual insurance and wealth management solutions through our licensed subsidiaries and affiliates.Our expertise is matched only by our personal commitment to each client’s goals.

Senior Vice President

Vice President

JLT Specialty USA is the U.S. platform of the leading specialty business advisory firm Jardine Lloyd Thompson Group. Our experts are specialty focused and have extensive experience in industries and products serving leading U.S. and global firms. We focus on complex areas of industry or product need, where innovation and optimization are critical. 

Our specialty team has clear alignment around our clients’ best interests and are judged and rewarded based on our clients performance. With decisive insights, our team is fact-based and analytics-driven to create the best insights and value for our clients. 

Our culture enables a rewarding and challenging environment to attract and develop the best talent in the industry. We encourage creativity and are free to challenge conventions. With teamwork and collaboration, we are working together to share knowledge, solve problems and deliver the best solutions for our clients. 

Jardine Lloyd Thompson is one of the world’s leading providers of insurance, reinsurance and employee benefits-related advice, brokerage and associated services. JLT’s client proposition is built upon its deep specialist knowledge, client advocacy, tailored advice and service excellence. JLT is quoted on the London Stock Exchange and owns offices in 40 territories with more than 10,600 employees. Our global foundation is unparalleled and provides experts worldwide in 135 countries. 

For further information about JLT, please visit our website www.jltus.com

Broker Director and Officer's liability insurance for clients around the globe.

Assistant Vice President

Development Intern

Developed Business Plan

Intern

Managing Partner & Co-founder of LION Specialty | Global Financial Institutions & Private Equity Broker  | Classical Certified Pilates Instructor

French

Most executives discover their D&O coverage gap the day they get sued—not the day they sign the policy.


Here's the brutal part:

CFOs and general counsels spend weeks negotiating premium rates and policy limits. But the language that actually determines whether you're covered? Most never read it.

I've reviewed hundreds of D&O policies. And the same technical gaps show up over and over.

These aren't edge cases. They're the exact provisions insurers use to deny claims when executives need coverage most.

Here are 3 policy traps that sink real claims:

1/ Fraud exclusion language with a "dishonesty”trigger

Vague fraud exclusions let the insurer deny coverage based on allegations alone—no final judgment required. Executives are left funding their own defense. 

✅ Protective: "Fraud as determined by final non-appealable adjudication"
❌ Risky: "Fraud resulting from dishonest acts" (no adjudication requirement)

2/ Hammer clauses forcing lowball settlements

This provision penalizes you for rejecting settlement offers the insurer wants to take.

Refuse a settlement? The policy limits your recovery to what you would've paid if you'd accepted.

✅ Protective: No hammer clause, or "modified hammer" (insurer shares excess costs)
❌ Risky: "Insurer's liability limited to settlement amount offered"

3/ Representations language that outright excludes coverage and relies on all being material

If your policy application becomes part of the contract, any misstatement—even unintentional—can be used to deny 

This includes statements made by people you don't even know about facts you can't verify.

✅ Protective: "Severability of applications" + "only material items to acceptance can be used to deny"
❌ Risky: "Application is part of this policy and all statements are warranties"

I've seen GCs negotiate policies for months and yet miss some key details like these

Which of these gaps exists in your current D&O policy?

The AI honeymoon is over for insurance.

78% of P&C insurers are using generative AI in some capacity. But Only 4% have scaled it across their organizations.

And that gap should tell you everything.

I've been watching this play out with carriers for the past year. Everyone bought the tools. Everyone ran the pilots. Everyone presented to the board about transformation. Now the boards are asking a different question: where's the return?

The carriers who actually scaled past the pilot phase did something different. They didn't start with "we need an AI strategy." They started with "renewals are slipping" or "quote turnaround is killing us" and worked backward from there.

Look at where the big carriers are placing their bets. State Farm, USAA, and Allstate hold 77% of all insurer AI patents. They're protecting claims automation, telematics, customer service. Boring stuff. Stuff you can measure.

For the carriers I work with, the question I keep asking is:

Can you tie your AI spend to a number? If the answer is no, that's worth a conversation before your next board meeting.

P.S. If you want to talk through how AI deployment is showing up in underwriting conversations, DM me.

“The stiff and unbending is the disciple of death. The gentle and yielding is the disciple of life". 


A quote from the Tao Te Ching. 

In building a business, being around friends at different phases of life, from different cultures, marrying someone of a different ethnicity, and trying at all times to immerse myself in culturally rich cities, I’ve found this to be true to almost an unnerving point. 

If you’re not willing to bend
Change your habits
Continually grow
Apologize for your wrongdoings
Shift your path based on another 

You’ll find yourself in the same place for most if not all of your life. 

I was reminded of this quote in finishing the book Atomic Habits by James Clear . 

While on the face it’s about habits, I took away more the ability to

- take what is automatic and make it a deliberate practice 
- Learn to master the process of narrowing your focus to truly the most important element of success
- Constantly review and reflect

And more importantly than anything learning to fall in love with the mundane. 

Why does any of this matter?

Because it’s what makes people great. 

To be applied anywhere of deep success:

Successful entrepreneur
White glove service
Professional athlete 
Fighter pilot
The charismatic wealthy friend who seems to have it all 

Which all comes with the desire to master as task but always being willing to grow. 

Most do not have this level of discipline especially these days with AI, social media, and attention spans being less than 10 seconds. 

So for those who fall in this camp.  I applaud you, and hope to meet you someday!

Happy Saturday. 

Ps. A brand that definitely has this dedication to constant improvement and refinement! Their location in France was quite the experience!
Ruinart

The single biggest leverage point in any insurance negotiation is time.


Most brokers start the renewal process 30 days before expiration.
They flood the market with submissions. They cross their fingers. They hope for appetite.
You get daily emails asking for "just one more thing" while trying to close your quarter.

We operate on a 150-day cycle.

Day 150: The Strategy
We map out exactly where we are headed. We identify the story we need to tell before we ever open a submission file.

Day 120: The Build
We construct the submission. We test every angle of the risk narrative.

Day 90: The Approach
The carriers see our first approach now. We are reading the market, not reacting to it.

Day 60: The Options
We have your options locked down.

Day 30: The Bind
Bindable terms in hand. No drama. No surprises.

One client saw their limits jump 25% at flat premium simply because we had the runway to position them properly.

You negotiate effectively when you control the clock.

If your renewal is July 1st, we should be starting right now.

DM me "TIMELINE" and I'll share our 150-day execution roadmap.

The client didn't trust me. I was young, the account was complicated, and standard solutions wouldn't work.

This was a $250K commercial account with exposure across 3 different liability classes. The existing broker had left gaps in coverage that put the client at serious risk.

And I had one shot to prove I could handle it.

Here's what I did to turn a skeptical prospect into a 7-year partnership:


Step 1: I stopped pitching standard packages

Most brokers would've pulled out their usual markets and called it a day.

Instead, I spent 6 hours reviewing their operations, claims history, and contract language. I found 4 specific exposure gaps the previous broker had missed—including one that could've cost them $100K+ in an uncovered claim.

I presented those findings before I ever mentioned a single carrier.

Step 2: I built custom manuscript forms for their unique risks

This client had operations that didn't fit into standard ISO forms. So I drafted manuscript policy language that actually addressed their exposures.

I used my background working with London syndicates to structure coverage that matched their real-world risk profile—not just what was easy to place.

Step 3: I showed them the math on every coverage decision

For each coverage gap, I laid out:

• The specific scenario that could trigger a loss
• The dollar amount they'd be exposed to
• The premium cost to close the gap
• My recommendation (and why)

No insurance jargon. No pressure. Just clear trade-offs so they could make informed decisions.

The outcome?

They signed. And years later, they're still a client.

Not because I sold them the cheapest policy or had the flashiest pitch.

Because I did the work to understand their business and gave them coverage that actually protected them.

That's what client-centric risk management looks like.

If you're a broker or risk manager, here's my question: What's one thing you could do today to understand your client's operations better before you present a single policy option?

I'd love to hear how you approach complex accounts.

If your insurance coverage doesn't work in a simulation, it won't work in a crisis.


We don't just place the coverage and file the binder.

We stress-test it.

Before the program binds, we run "Mock Claim" scenarios against the proposed language.

We simulate the specific nightmares that keep the C-Suite awake:

1. The Friday Night Hack

A ransomware event hits at 6 PM. Who do we call? Does the "Breach Response" definition actually trigger immediate counsel, or are we stuck waiting for carrier approval?

2. The Regulatory Subpoena

A short-seller report triggers a stock drop. The SEC calls. Does the policy cover the "Informal Investigation" costs, or does it only trigger after a formal Wells Notice?

3. The Nuclear Verdict

A jury awards $50M. Does the excess tower sit flush on top of the primary, or is there a gap in the attachment point that leaves you exposed?

We usually find the cracks during the simulation.
It is infinitely better to find them in a conference room than in a courtroom.

You stress-test your software.
You stress-test your financials.
Start stress-testing your risk transfer.

Ready to see if your program holds up?

DM me "STRESS TEST" and let's run a scenario.

Ps. This is how we react when we hear of another prospect’s program not working and they need a LION!

There is a quiet dysfunction that plagues even the best mega-brokerages.


It’s the account manager who doesn't remember the coverage conversation from six months ago. It’s the service team that treats every interaction like a fresh start. It’s the senior partner who shows up for the sale, then vanishes until the renewal.

How do we know this?

Because we lived it for decades.
We thrived inside the machine. We did exactly what the industry required: we wore "exhaustion" like a badge of honor.

Long hours. Weekly travel. Drinking too much.
We kept telling ourselves, "It's just the business. It's just the way it is."
Reality: it was grueling and massively unhealthy.

It became crystal clear when my co-founder Flip and I walked away from it all at the end of 2022.
It took us six months just to decompress.

I spent that year getting certified as a Pilates instructor.
Four hundred fifty hours of training.
I watched high performers show up depleted, push through, and then return to environments that broke them down.

My insight was sharp:
"The workout wasn't the problem. The recovery system didn't exist."

Meanwhile, Flip was coming to the same conclusion from a different angle.

A friend recommended The Blue Zones Kitchen.
He started studying Okinawa and Sardinia—places where longevity is a system, not an accident. 

A concept which I’ve long been interested in since my nana lived to 103!

We realized the industry’s problem wasn't training, technology, or talent.

The problem was that the people serving you are running on empty.

So we asked: "What if we built a brokerage using Blue Zone rules?"

A place where high performance doesn't require normalizing anxiety.

This is what we built—and why a "Corporate Blue Zone" is the safest place for your risk program to live.

If you didn’t catch it, we wrote about this in our Wednesday intelligence which dropped yesterday. Want a copy - comment WEDNESDAY.

This is what we want every client to experience. 

White glove service:

getting back to you quickly, not wondering where we are, and knowing we will always come through for you. 

Creativity and “bespoke” solutions:

So many brokers move through the motions but actually understanding a client’s risk profile means the difference between average and exceptional results. 

To feel like they are our only client:

We strive for high touch, responsive, creative, early, easily reached, results oriented, and positive so that every client feels like they are our only client. Their size, location, and risk profile does not matter in terms of our attentiveness - each one is equally importantly. 

Thanks Brooke!! This made our week!

General Counsel at American Coastal Insurance Corporation

We made the switch to Lion Specialty and immediately saw exceptional results. Everything highlighted in their recent newsletter mirrors our own experience — responsive service, technical expertise, and a true solutions‑focused approach. The Lion team delivers exactly what they promise, and the impact on our placements has been clear. A great read from a partner who really follows through.

https://lnkd.in/eskSdDcQ​

Open article: What Fortune 500 CFOs get that you don't by lionspecialty.ck.page

Your D&O policy protects the company. But when you get named personally, does it protect you?

Securities lawsuit risk has climbed to $13.7 trillion. AI disclosure pressure keeps growing. Personal exposure for executives is no longer a concept.

Side A coverage gaps. Exhausted limits. Severability failures. These determine how personal assets get exposed when claims get serious.

Coverage that exists on paper differs from coverage that performs when you're the one being named.

Most brokers serve institutions. Fewer serve the executives who lead them. That distinction matters when a regulatory investigation or shareholder action makes your D&O policy suddenly personal.

What financial institution executives actually need from their broker: time back in your day, personal protection that holds up under pressure, and board-ready answers when your directors start asking questions.

If you haven't examined how your D&O program would actually perform under stress, now is the time.

P.S. We built a 5-day email course on the D&O mistakes we see most often. Comment BLUEPRINT and I'll send it.

Executives, there are two ways to protect your personal assets and your financial institution’s balance sheet in 2025…

1. Buy insurance. Hope it works.

2. Engineer a risk management program so resilient, it becomes a strategic asset.

Many still do the first. 

Even the sophisticated ones.

That’s why I’ve spent 25 years - and over 85,000 hours - mastering the second.

From building multimillion-dollar divisions at Marsh, JLT, and NFP…to recovering over $250 million in claims for clients…to founding LION Specialty, a boutique insurance firm built for the institutions who can’t afford to settle for off-the-shelf solutions.

Today, I help financial institutions, private equity firms, and insurance carriers, MGAs and ILS funds:

→ Navigate the global insurance markets.
→ Gain direct access to the best underwriters in the U.S., Bermuda, and Lloyd’s.
→ Structure D&O, E&O, Cyber, and complex P&C programs that hold up under real-world stress.
→ Align coverage with board priorities and capital strategy, not just next year’s premium.

We stress test programs annually like regulators would. 

We optimize every renewal. 

We've honed our claims playbook over three decades. 

Because in our world, you don’t get rewarded for being insured. You get rewarded for being prepared.

Building the New Standard:

At our insurance brokerage firm, LION Specialty, we’re building more than a brokerage. 

We’re building the broker of the future...

→ Delivering boardroom-grade insights to thousands of institutions through our weekly "Boardroom Briefings," and daily insights via our social platforms.
→ Attracting elite talent through a high-performance compensation model and culture.

Our mission: 

Obsess over every detail, so you don’t have to. 

Obsess over our execution. 

So you feel like you’re our only client! 

If your institution is ready to rethink insurance as more than a commodity - and turn it into an edge - I’d welcome an opportunity to connect! 

- Mark “FLIP” Flippen 

Mark Flippen

A Lloyd's underwriter once told me:
"I am not betting on the spreadsheet. I am betting on the people."

That advice saved my clients millions over the last 20 years.

I was 28 years old. I was sitting across from him at my first PLUS event. He was a veteran underwriter from a well known Lloyd’s syndicate. 

He had been u/writing D&O since before I was born.

I had my stack of papers. My charts. 5 years of loss data. I was all ready to go thru the math.

He didn't look at the papers. He looked at me and asked one question…”If the building burns down, will they try to save the furniture, or will they let it burn?"

This was an inv mgmt account. Why was he asking about the building burning down!

Still makes me chuckle. 

That moment though. It changed how I viewed the trade.

The "spreadsheet" broker thinks risk is a math problem. They think if they tweak the deductibles enough, if they best position the financials the risk diminishes.

The "Trading" Broker knows risk is a human problem. We don't just sell your data to the market. We sell your character to the market.

What’s your move when it hits the fan. 

When we bring a deal to market, we don't just send the PDF. The submission. We tell the story of the management team. We explain why you are a safe bet.

20 years on, that underwriter is still right. The spreadsheet tells you the price. The story tells you the risk.

And the best terms always go to the “people,” w the best stories.

I Help Executives Turn Insurance Into A Competitive Asset & Protect Their Personal Net Worth | Managing Partner & Co-Founder of LION Specialty | Expert in Corporate Liability Insurance 

There are two ways to protect a financial institution in 2025:

1. Buy insurance. Hope it works.
2. Engineer a risk management program so resilient, it becomes a strategic asset.

Many still do the first. Even the sophisticated ones.

That’s why I’ve spent 25 years — and over 85,000 hours — mastering the second.

From building multimillion-dollar divisions at Marsh, JLT, and NFP…to recovering over $250 million in claims for clients…to founding LION Specialty, a boutique insurance firm built for the institutions who can’t afford to settle for off-the-shelf solutions.

Today, I help financial institutions, private equity firms, and insurance carriers:

→ Navigate the global insurance markets.
→ Gain direct access to the best underwriters in the U.S., Bermuda, and Lloyd’s.
→ Structure D&O, E&O, Cyber, and complex P&C programs that hold up under real-world stress.
→ Align coverage with board priorities and capital strategy, not just next year’s premium.

We stress test programs annually like regulators would. We optimize every renewal. We've honed our claims playbook over three decades. 

Because in our world, you don’t get rewarded for being insured. You get rewarded for being prepared.

Building the New Standard:

At my new insurance brokerage firm, LION Specialty, I'm building more than a brokerage. I’m building the broker of the future...

→ Delivering boardroom-grade insights to thousands of institutions through our weekly "Boardroom Briefings," and daily insights via our social platforms.
→ Attracting elite talent through a high-performance compensation model and culture.
→ Making every client feel like they’re our only client.

If your institution is ready to rethink insurance as more than a commodity — and turn it into an edge — let’s talk.

- FLIP

Weekly Boardroom Risk Intelligence

CEO & Co-Founder, LION Specialty | Insurance Broker | 25+ Years Helping Insurance Companies, MGAs & Insurtechs Protect Their Executives & Balance Sheets | $250 Million Claims Recoveries | Corporate Liability Specialist

I drove into Boulder, Colorado with a bonfire raging in the bed of my pickup truck.

It was 1999.

I was on a date with a lady named Julie. I was trying to show her my rugged outdoorsman self. A couple of years before I had completed my Outdoor Semester in the Rockies. 

Grand plan. I’d take her camping and show her how cool I thought I was! 

A little camping trip in the foothills would be the perfect spot. But it started pouring rain, so we threw everything (including the charcoal grill) into the back of my Toyota Tacoma and bailed.

I thought the fire was out.
The 60mph wind on the highway had other ideas.

By the time we parked, flames were licking the tailgate. She was terrified. I thought, "Well, that’s it. She’s never going out with me again."

She didn't run though. 
She laughed. 
And then she helped me put it out.

That was 25 years ago.
And that lady has been helping me put out fires ever since.

She was there when I was fired two months before our wedding.
She was there when we moved across the country to NYC with nothing but a plan.
She was there when I walked away from a cushy salary to start LION Specialty from scratch.

In business, we talk a lot about "partners."
But the most important partner you will ever choose isn't on your cap table.
It’s the one waiting for you at home.

Find the person who will ride with you when the truck is on fire! 

And never let them go.

A smooth renewal usually means nobody looked.

A mutual insurance company brought us in to review their own program. Their biggest agent, the one who sells for them, had been handling their corporate D&O and E&O for years. Long-standing relationship. Comfortable renewal. Felt efficient.

The problem is incentives.

That agent's job is to maintain a smooth, profitable relationship. Not to run a technical review that exposes gaps and creates friction. The renewal feels easy because it's just a rollover of last year's terms.

We ran their program through our 8-point stress test. Market positioning. Carrier selection. Coverage structure. Benchmarking against peers. Limits. Retentions. All of it.

We found over a dozen significant coverage gaps.

Problematic fraud exclusions buried in the policy. Vague allocation language that lets carriers decide how much of a claim is their problem versus yours. Notice provisions that were a trap.

A relationship renewal will miss these 100% of the time.

We put our manuscript form next to the vanilla form they'd been sold. The difference was undeniable.

The technical review was the foothold. That's what proved acumen over convenience.

They now trust us with their entire P&C and financial lines placement.

I had two uncomfortable conversations last week. And sadly, I plan to have a dozen more before the quarter ends.

First with a CFO, next was General Counsel. 

Back-to-back insurance policy reviews. Many executives would rather have oral surgery than do an insurance review. Believe me, I get it.

But both execs looked at the coverage concerns we found and asked the exact same question. 

"Why didn't my broker catch these?"

After two decades, I still hate answering that question. Because the answer gets uncomfortable. The gaps we find are rarely complex. 

They’re systematic service failures. Your broker just wasn’t looking, sir. Or worse, they don’t have the skill set to see these, madam. 

• Fraud exclusions that trigger too early.
• Allocation language that is vague on purpose.
• Notice provisions that fail during a crisis.
• D&O and E&O programs that don't talk to each other.

Last week weren’t "typos." They were foundational risks that are leaving these executives’ personal assets exposed. And the balance sheet with a false hedge.

Why this is happening now…

For years, the mega brokers have moved business that doesn’t generate $1M in commission into Small Business Units. The aspiring big brokers have copied this model like lemmings. That means one broker handling 200+ accounts at a time. Even a super broker can’t manage that kind of load.

And we all know the super brokers aren’t in the small biz units. 

So your program — which is meant to protect the board, the balance sheet, and your personal assets 
— gets transactional service. 

Add to that the recent agitation. 

All that broker consolidation you’re reading about in the industry rags. 
Your "trusted advisor" is distracted by their own merger. Their new company bogged down w internal crap. Your team is in flux. And litigation might be blocking you from the talent you actually hired.

All the while...

We are in a market with the most favorable terms we've seen in years.
But you can't access them if your broker is distracted, or just hitting renew.

If you are a CFO or GC at a financial institution and you haven't stress-tested your program in the last 12 months, let us help you. 

Grab a time on my calendar. Link👇🏻

Your coverage either works when you need it, or you find out it doesn't.

PSA: you can’t automate the knife and fork, yall. I know, some of you are bummed out. Nor can you AI the lunch convo or the fight across the country to close the deal. Sorry!Those were my reminders this week. 

No Zoom or Microsoft Teams calls with a PowerPoint. Just face to face with a new client whose deal we won at the lunch table! Ok, full disclosure we did bring a PowerPoint. Old habits die hard! 

We also took this cool picture with a Steel LION after the win. 

Then we waited for new client to drive away. Then TASH and I had a round of high fives and a fifteen to twenty second dance party in the parking lot of Cap Grille to celebrate! 

Man, it was awesome.
Winning new clients never gets old. 

P.S. hard to compete w a team that’s having fun! 

LION Specialty

"Be a student of the game." You’ve heard it a million times. But here’s why every young professional specializing in anything should consider it. 

( especially in our industry ) 

It’s arguably the best advice I ever received as a young insurance pro. 

Just behind: “be nice to everyone, you never know who you’ll be working with or for!” And if you are just starting out, it’s the only advice that matters.

How that simple phrase changes everything:

1. The "Game" makes it fun.

If you view this industry as a "job," you will burnout.

You will dread the paperwork. You will resent the long hours. But if you view it as a Game, your competitive instincts kick in. Every sales call is an at-bat. Every renewal is a playoff game. Every deal you bind is a point on the scoreboard.

Suddenly, you aren't "working." You are playing to win.

2. The "Student" makes you dangerous.

Most people in this industry are "tourists."

They know enough to pass the exam, but they don't know the deep mechanics. When you commit to being a Student, you stop skimming the surface. You read the policy forms on the weekend. You study the exclusions. You figure out why the underwriter said no, so you can make them say yes next time.

The tourists get paid a salary. The students of the game build empires.

Don't just show up for work today.
Study the playbook. Learn the rules.
Then go win your game.

What was the best advice you got early in your career? 

P.S. 2012 this is me in my first nice suit in my first nice apartment in Hoboken! 

I had been playing the game in NYC for a few years by then and it was starting to pay off!

After 25+ years in insurance, I've watched too many talented people sacrifice too much for “success”... 

The traditional insurance model is:

→ Individual producers grinding alone
→ 60+ hour weeks disguised as "dedication"
→ Compensation structures that pit teammates against each other
→ Knowledge hoarding as competitive advantage
→ Burnout treated as inevitable

( for pros trying to be elite ) 

So we‘re building something different..

An “Insurance Blue Zone.” Seems a bit woo woo at first! But, give me another min here…

When we look at the world's actual Blue Zones - regions where people live to 100+ at extraordinary rates - you see their longevity comes from their systems.

And the principles that create longevity in Italy, Japan, California are ones you’ll see in LION.

1. Purpose Over Performance

Blue Zone communities have ikigai - reason for being. 

At LION, we solve problems that matter instead of chasing revenue targets. When your work has meaning beyond metrics, sustainable intensity replaces destructive grinding.

2. Community Over Competition

Centenarians in Blue Zones live in tight social networks. 

We structured LION as "Elevated Ensemble" - shared success, collective expertise. Knowledge flows freely because everyone wins when anyone wins.

3. Movement as Medicine

Blue Zone residents walk naturally throughout their day. 

Our workflows eliminate artificial urgency. Steady progress over frantic sprints. 150-day renewal orchestration instead of 90-day panic cycles.

4. Stress Resilience, Not Stress Avoidance

Blue Zone communities face challenges but have strong support systems. 

We embrace complex risks but tackle them systematically as a team. "Crucible Forged"—edge earned under pressure, together.

5. Sustainable Rhythms

Blue Zone eating patterns: regular, moderate, mindful. 

Our workload design prevents feast-or-famine cycles. Consistent quality over erratic heroics.

These principles have led to:
→ 92% team retention over 20 months
→ 30% faster project delivery
→ Zero compromise on quality
→ People actually want to be here 

We stopped asking, "How do we make people work harder?"

And started asking, "How do we help people thrive longer?"

Most firms push until people break.

We built a system where excellence is the natural outcome of sustainable practices.

The insurance industry treats burnout like a badge of honor.

But the world's healthiest communities prove that longevity will always beat intensity.

P.S. I wrote about our Blue Zone in our latest “Wednesday Intelligence,” blog series yesterday. See link in comments…👇🏻

You cannot read the label from inside the bottle. Yet so many smart MGA executives try to anyway.

Over our 20+ years, we’ve seen a lot of factors that drive this. We saw it four separate times just last year.

Each time, the MGA had brilliant in-house people who understood financial lines. Some were ex-underwriter friends we had traded with in the past. A few had even been underwriters and brokers.

Love you guys, but this is how you get out over your ski tips!

You’re smart. Tons of experience. And because of this keen institutional knowledge, you try to structure your own D&O and E&O insurance deals. 

The thought: "why do we need a broker? We know our business better than anyone."

In all our cases last last year they were right. They did know their business better than anyone.
But they recognized their gap was knowing the global market.

They realized they were operating with a sample size of one.

They only saw their data, their history, and their specific exposures. So they made a strategic move.

They decided to zoom out.
They stepped out of their silo and used us to help them access the global market—London, Bermuda, the US.

By partnering with a specialist team, they gained visibility into where the capacity was hiding. They knew which levers to pull to create more competition.

The transformation…

→ They leveraged our proprietary Lloyd's form to get broader coverage than they could have negotiated alone.

→ They created the right competition that drove down their pricing.

→ They have the LION process and platform in place to stress test their program annually now too! 

They didn't need us to be "smarter" than them.

They just needed a better map.

And they were smart enough to ask for it.

The value of a specialist broker isn't just "doing the transaction."

It's the process you use to see the whole deal.

how elite MGAs go to market:

Moltbot's this week's headline. Agentic AI is the real story.
But here's what the tech press missed...

An AI that actually does things went viral last week. 44,000 developers. Cloudflare stock up 14%.

And this is exactly what's coming for insurance. Every function. Every department. Every part of the value chain. In many ways it's already here. 

The shift:

For two years, AI meant chatbots and document summaries. Useful. Not transformational.

Agentic AI is different. You give it a goal. It figures out the steps. It executes.
And it's the part that changes everything.

Underwriting:

Submissions that will auto-triage, pull loss runs, check appetite, and bind small risks — no human touch required. 

Your underwriters stop processing paper and start making judgment calls on the risks that actually need them.

Claims:

Systems that don't summarize files — they will help adjudicate. 

Real-time settlement for straightforward losses. Fraud detection running in the background. Your senior adjusters focus on complexity and negotiation, not data entry.

Distribution:

This one's uncomfortable. Consumer AI agents that will shop carriers via API. Price, coverage, claims reputation — all compared in seconds. Carriers that don't embrace this will lag behind those that do in many parts of the industry. 

If your quoting process requires too many phone calls and PDF applications, you become invisible to the next generation of buyers.

The risk nobody's underwriting:
Moltbot also proved the vulnerability. Prompt injection — one malicious message, and the AI acts on it automatically.

Silent AI risk. Accumulation exposure. Most cyber and E&O towers weren't built for this.

The board issue:

Everyone's asking about AI strategy. Few are asking about AI exposure.

If you've gotten this far and you dont know what Moltbot is...We broke it down and the security issues in yesterday's Friday Five Boardroom Brief. Link in the comments.

Like it? Subscribe. 

We do it every Friday. It's the fastest growing insurance newsletter in the industry! Because it's written by people actually in the market, not just reporting on it. 

Stay covered y'all 🦁

Median jury awards climbed from $21 million to over $51 million in five years.

Yet, risk costs? Still trending down. 

Thermonuclear verdicts exceeding $100 million appeared 27 times in 2023. In the previous decade, there were roughly three.

Traditional exposure models are becoming dangerously outdated.

Plaintiff attorneys use what's called the "Reptile Theory" to bypass logic entirely. They trigger primal survival instincts in jurors. The goal is to make the jury feel like the defendant's conduct threatens the community's safety. Once that switch flips, rational damages calculation goes out the window.

The nationals are responding with million-dollar defense strategies.

But regional and mutual insurers have an overlooked advantage: community presence.

Your adjusters living in town and coaching Little League is better verdict prevention than anything the nationals can buy. Jurors are less likely to deliver nuclear verdicts against companies they see as neighbors.

The era of predictable verdicts is over. Your D&O limits need to reflect that.

P.S. We built a 5-day email course on the D&O mistakes we see most often. Get started here: https://lnkd.in/gVzZgGPW

Is this the biggest 2026 risk exposure for financial services firms? Especially for regional, mutual insurers, MGAs and insurtech & fintech companies? 

Last year a Chinese hacking group attacked 30 institutions at the same time. 

But they didn't have 50 hackers.

They jailbroke Anthropic’s AI coding tool (Claude Code) gave it access to command lines and file systems, and pointed it at targets.

The AI did 80-90% of the work autonomously. It scanned networks, found weak spots, and broke in at machine speed. Thousands of attempts per second.

It failed most of the time. 

Hallucinated credentials. Tried to steal documents that were already public. Clumsy.

Yet clumsy at machine speed is still dangerous. It only has to get lucky once. And while your security team chases all the noise, the real attackers slip in the back.

Meanwhile, many of your cyber policies were written for human hackers. 

Most policies are silent on AI attacks and autonomous AI agents. And while silence in some of your other lines of coverage like D&O and E&O might be favorable to you. Silence for this type of new attack in cyber insurance is dangerous.

There’s virtually no case law yet to show us how the ambiguity in coverage will work. Will it favor the insured? Or the insurer? 

If you’re buying cyber you should read this. 
If you’re writing cyber you should read it, too. 

If your policy doesn't say "Artificial Intelligence" explicitly, you might be holding a blank piece of paper when the claim hits.

We broke down the full Salt Typhoon event and what it means for cyber renewals. Comment NEWSLETTER for the link.

And if you’re not on our distribution and you want weekly updates and breakdowns like this, join 2500+ financial institution executives receiving our Boardroom Briefings. 

https://lnkd.in/gP22wvyF

P.S. The diagram below shows the different phases of the attack.

Florida just dropped from 2nd-10th in national nuclear verdict rankings. And that’s only part of the story.

Seven other states are running their own similar tort reform plays. With a half dozen others right behind them. Strong momentum nationwide. 

Some highlights of our National Tort Reform update in this week’s LION Specialty Boardroom Briefing…

→ Georgia banned anchoring
→ Louisiana moved to a 51% fault bar
→ Third-party litigation funding is now being treated as a national security concern

As it should be! 

Is this the sauce that helps replenish much needed capacity across the nation? You tell us…Let it rip in the comments below. 👇🏻

In other news…the tale of the most unusual market I’ve seen continues. 

Experian’s recent cybersecurity annual report is out. Financial services companies are the #1 target for cyber attackers  -  387 breaches in the first half of 2025 alone. Significant cybersecurity risk profile volatility, but the soft market cycle remains for cyber insurance. 

Grumblings from the market aside, it continues to amaze me! 

If you want these summaries, along with our takes on how these events are moving the global insurance markets, and you’re not subscribed to our weekly Briefings? Comment "GAMETIME" below and we’ll get you on our distribution…

Over 2,500 financial services executives receive this quick five minute skimmable read every week now. 

The LION Specialty “Friday Five”Boardroom Briefing! 

Stay current / stay covered yall!

P.S. Want to map your litigation exposure by state? DM me  -  happy to walk you through what we're seeing on recent renewals.

I didn’t call the "Claims Hotline."
I called Mike. He thinks the burgers at J.G. Melon are the best in the city.
Unless he can get you to Queens for the Fillmore's Tavern burger!

Contrary to popular belief, claims aren't paid by logos. They’re paid by people.

When the worst day of your career happens. Or when the lawsuit lands in the WSJ, you can feel incredibly small. Or defensive. You feel like you are up against a faceless machine designed to say "No."

And in many ways, that’s right. 
There also another side. 
That’s way more human. 

Because behind every "Big Carrier Name" is a claims adjuster. A guy like Mike. 

Behind every reservation of rights letter is a person making a judgment call.

If that person sees you as a "File Number," they will stick to the rigid letter of the contract. They may look for reasons to minimize the cost.

But if they see you as a Partner.
Or better yet, an actual human being they can get a burger with everything changes.

This is the human side of Claims Advocacy that no one talks about.

It not about War Rooms like many will tell you. It’s about the relationship capital teams like ours have built long before the disaster happens. 

We’re not just emailing these adjusters when things go wrong.
We know them. We respect them. We view them as allies, not adversaries.

Because we have built that bridge, we can pick up the phone and turn a conflict into a conversation. We can say, "I know what the exclusion says Mike, but let's talk about the intent."

And because there is trust, they listen.

You can have the perfect policy language and still lose the claim if you have the wrong partner.

Where are my claims people at?

Stay covered out there everybody!

Mike Approved Executive Guide to Claims Advocacy 

What do DEI programs and billing fraud have in common?

For those of us around during the credit crisis years, you’ll likely remember when 19 of the top 30 banks got crushed, the last time the DOJ dusted off the Civil War Era False Claims Act! 

That was for lending services. 
Now it’s diversity, equity and inclusion. 

DOJ just launched False Claims Act investigations into corporate DEI programs.

Billing fraud? Nah. 
Not defense contractor over-billing either. DEI practices.

CFOs, GCs, and board members at regional insurers, reciprocals, and mutuals…maybe all financial services companies. 

This could affect you if your institution has federal touchpoints — SBA relationships, TRIA coverage, federal program participation.

In my 20+ years placing coverage for financial institutions, I've seen the pattern:

→ Whistleblowers can initiate lawsuits even if DOJ declines — and collect a percentage
→ The investigative phase alone imposes significant document production and reputational costs 
→ The time to build the paper trail is before anyone asks for it

If you want the framework sophisticated institutions use to treat compliance as balance-sheet protection…

…read about it in this week's LION Specialty ‘Friday Five’ Boardroom Briefing.

Comment "BRIEF" below if you're not on our distribution…

Stay covered out there everybody!

P.S. If you're wondering whether your certifications create FCA exposure, let's talk. 

DM me

And join 2,500 financial services executives reading our weekly Briefs…

https://lnkd.in/gP22wvyF

There is a quiet dysfunction that plagues even the best brokerages. 
We built something different. Inspired by the world's Blue Zones. Regions like Okinawa and Sardinia where people live longest due to their systems, not their genetics—we designed an environment for professional longevity. We call it the Insurance Blue Zone.

There is a quiet dysfunction that plagues even the best brokerages. It’s the account manager who doesn't remember the coverage conversation from six m

LION Specialty's Blue Zone

How to know if your insurance coverage will actually respond during a claim—in under 3 minutes:

(buyers, trust but verify your structure)

After 20+ years negotiating coverage for financial institutions and private equity firms, I've found every program that actually works passes three tests.

Swipe through to see if yours would pass →

AXIS surveyed 500 CEOs and CISOs. The results expose a fault line rifting in boardrooms across the country. 

( operators, here’s the summary ) 

CEOs are 10 points more optimistic than CISOs that AI will strengthen cyber defenses.

But here’s the contradiction that should concern you:

— 82% plan to increase cybersecurity budgets over the next 12 months
— 75% plan to cut cybersecurity headcount because AI tools will make remaining staff more productive

Wait, what? 

Read that again. Budgets up. People down. While AI-driven attacks are viewed as the greatest emerging cyber threat. And possibly the biggest risk profile threat for insurance operations. 

The generational gap runs even deeper…Only 23% of executives over 55 believe AI improves security. 77% of those aged 35-44 do.

Meanwhile, CISOs rank “Shadow AI”or unauthorized tools employees deploy without IT oversight — as their top risk.

AXIS’s Lori Bailey put it plainly: “While it is now commonplace for CEOs to champion AI as a catalyst for innovation and efficiency, CISOs tend to see it as a new frontier of exposure and control.”

Your board probably has this same disconnect.

For our regional and mutual insurance company clients…

If your last cyber briefing came only from the CEO, you’re missing half the picture. And your D&O policy doesn’t care which executive was more optimistic.

We break down governance gaps like this every Friday. 

Here’s a link to last week’s Briefing:

https://lnkd.in/gNcA_WhF

If you like it, please sign up!

P.S. we’re also developing a 5 minute audio version too, if you prefer to listen. Here’s a sample…

My claims advocate opened the file and started naming people, not policy provisions. That taught me everything about how claims actually work.
It was my first big claim. SEC suit against an investment management client.

We bring in Ed, our senior claims advocate and attorney, to help manage the response. I'm expecting him to dive into the policy. Start reading provisions. Analyze coverage grants. Review exclusions.

Instead, he opens the file and says: "Ah, good. We got Greg."
(Greg was the underwriter.) Then he says: "And my buddy Sarah handles claims for Greg and their team."

He knew them by name. Knew their track records. Knew how they operated.
I thought we were there to review coverage. To design response. He taught me we were there to work with people.

Policies don't respond to claims. People do.

The policy language matters. But the people interpreting that language matter more. Ed spent the first 30 minutes teaching me about how Greg and Sarah work. Not about their company—about them specifically.

How Greg approached gray coverage situations. How Sarah worked with brokers during claims. What their track record looked like on similar situations.

He said: "These are good people to have on a claim. They won't be easy. They'll be tough. But we always seem to get to a reasonable place with them."

That was the tell. "A reasonable place."

Here's what I learned: most claims aren't black and white.

They're not "this is clearly covered" or "this is clearly excluded." They live in gray areas where the policy language could go either way.
And in those gray areas, the people on the other side of the table often determine the outcome.

Some carriers approach gray coverage asking: "How can we deny this?"
Others ask: "How can we cover this?"
That difference is everything.

Twenty years later, the people are still how we select carriers.
My teams don't just evaluate policy forms. We evaluate who will be in the room when our client's business is on the line.

Because coverage is only as good as the people who honor it.

Let's connect if you want a broker who's been through this before.

Executives Guide to Claims Advocacy

“ Everybody can be great... because anybody can serve. You don't have to have a college degree to serve... You only need a heart full of grace. A soul generated by love." Dr. King

A health insurer embedded an off-the-shelf AI solution into their claims process. Regulators asked how it worked. 

The company said they didn't know! 

Florida's insurance commissioner is now pushing two bills that would require humans in the loop whenever a claim is denied.

Other state regulators are watching.  

Rep. Hillary Cassel filed HB 527. Sen. Jennifer Bradley filed SB 202. House Speaker Daniel Perez declared December 8-12 "Artificial Intelligence Week" with subcommittees examining AI across their jurisdictions.

Commissioner Michael Yaworsky outlined his framework to the Senate Banking and Insurance Committee: disclosure when AI is used, auditing that confirms systems do what they're supposed to do, and a human in the loop who actually understands the technology.

He's not calling for AI elimination. "I'm not an opponent of AI," he told lawmakers. But he wants carriers to be able to explain what their systems do.

The bills aren't law yet. But the regulatory direction is clear.

Quick question: if someone asked your team to explain what your AI systems do, could they?


P.S. We built a 5-day email course on the D&O insurance mistakes we see boards make most often and how to fix them. Comment BLUEPRINT and I'll send it.

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The Battle

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