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Insurance is Frustrating

steve901879
Apr 12, 2025
1 min read

Updated: Apr 16, 2025

We often hear insurance is broken, our clients disagree.

First, to establish the brokenness of insurance by correlating the value buyers place on it.

If you value insurance at zero, then any inconvenience is too much.

But when you’ve spent your career perfecting, litigating, and negotiating corporate insurance (D&O, Tech E&O, EPL, Cyber) for complex companies, you have a different POV.

Insurance isn’t broken, it is hard (frustrating) to get it right.

But there is solace - once your broker gets it right, just once, you can just renew it each year with minor inconvenience.

Much of today’s innovation in insurance has focused on ease - automating applications, speeding up quotes, simplifying UX. That’s a great step. And for certain types of P&C insurance (property, auto, small commercial) convenience alone may make sense.

But corporate insurance isn’t convenience-driven - it’s consequence-driven.

D&O, Tech E&O, Cyber, EPL - these are not off-the-shelf products for companies with any complexity. They are sophisticated contracts designed to respond when a company is under real pressure:

A board is named in a lawsuit.
A regulator launches an investigation.
A key employee files a claim.
A funding round is disrupted by a pending dispute.

These moments aren’t rare anymore. They’re part of the operational reality for investors and tech companies. And in those moments, the structure of the policy, not how fast you purchased it, determines the outcome.

I’ve been on both sides of these situations - inside the claims, on the broker side, and as an attorney across the table in negotiation.

And I’ve seen something few talk about: It’s easy to dance around simple coverage language when you need settlement leverage.

In a dispute, vague language becomes a tool. In a deal, exclusions can be used to stall or squeeze. In litigation, unclear terms open the door to pressure tactics and second-guessing.

That’s not theory. That’s the reality of corporate risk.
And when the policy isn’t clear (when it wasn’t negotiated thoughtfully) the insurance company will structure it to exclude the most common claims. I.e. it will rarely hold up the way the buyer hoped it would.

(Happy to discuss hypothetical scenarios if you DM me)

Insurers write thousands like it, and they’re tracking every claim, industry trend, and governance signal.

If a buyer shrugs off the process, views insurance as just compliance, or chases speed over substance, insurers notice.

They don’t see confidence.
They see a red flag.

A company that treats insurance casually may treat risk casually too - and that’s exactly the kind of exposure insurers limit coverage for.

If you push for speed and pricing above all, don’t be surprised when you get a fast quote…with low coverage and little advocacy.

For over 15 years, I’ve seen one pattern hold true:
Sophisticated companies don’t just buy a policy - they shape it.
They work with a broker they trust
They compare coverage across markets
They ask smart questions about exclusions and definitions
They involve their GC and CFO - not just to sign, but to understand
They plan for scenarios most buyers aren’t thinking about

When a claim or investigation hits, they aren’t scrambling.

They planned for it.

The next wave of insurance innovation isn’t about faster portals.

It’s about applying professional judgment at the point of placement.

That means:
Educating the buyer—not oversimplifying the product
Asking better questions—not fewer
Aligning coverage with how a company actually operates and grows—not just what a form says it should pay

Because the value of insurance doesn’t show up when you buy it.

It shows up when you need it.

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