Before You Build the Tech, Understand the Risk

Why most insurtechs still aren’t ready for the enterprise insurance market.

By Steven Barge-Siever, Esq.

In insurance, it all sounds the same at first. A policy is a policy. A broker is a broker. Property & Casualty (P&C) covers everything, right?

But once you're on the inside - especially at the enterprise risk level - you see things for what they are:

Not all risk is created equal. Not all coverage is “commercial.” And not all brokers are in the same business.

Yet many insurtechs continue to treat billion-dollar companies and sidewalk cafes like they're buying the same product. And this is why my professional colleagues see no threat from insurtechs.

If you want to build real tech for real risk, you need to start with the fundamentals: Understand the risk. Learn the language. Respect the complexity.

Not All Insurance Is Commercial. Not All Brokers Are Equal.

At the small business level, insurance is mostly standardized. A general liability policy for a boutique or barbershop can be quoted online in minutes. It works — for commoditized risk.

But once your business has:

• A board of directors

• Venture investors

• Sensitive data or AI decisioning

• Multi-jurisdictional employees

• Enterprise customers with indemnity clauses

…you’re in another league.

You’re not buying coverage. You’re protecting capital, leadership, and reputation.This isn’t “commercial insurance.” This is corporate risk.

Visual Contrast: BOP vs. $15M D&O Tower

Barbershop BOP	Series B Fintech D&O Tower
$500/year premium	$15,000,000 in policy limits
Covers slip-and-fall	Covers regulatory subpoenas, securities claims
Standard ISO wording	Custom manuscript language
Retail quoting platform	Broker-led negotiation + legal review
Application: 1 page	Application: financials, cap table, governance
Low-impact litigation	Board/investor-level personal liability

One isn’t better than the other. But they are not the same product.

And yet, most insurtechs treat them as though they are.

Where Language Collapses, So Does Credibility

We see it all the time: platforms built for scale that collapse everything into the P&C or “commercial” bucket. Nuance disappears. Risk is flattened. Vocabulary collapses.

And it’s not just a branding issue. It’s a functional problem.

“When I hear a founder say they’re automating the ‘entire commercial insurance market,’ I know they haven’t spoken to a single wholesale broker.” - Managing Director, National Brokerage

A Real Breakdown: When Generic Coverage Meets Complex Claims

I worked with a Series B Fintech company whose previous broker bundled Cyber and Tech E&O into a generic “commercial package.” Sounds good, feels efficient.

The problem? The policy's Definition of Professional Services to excludes financial services.

My first thought - their broker is out of their depth. That’s what happens when you treat real risk like a template.

Language Is the Product

In this world, language is risk. Policies are legal contracts. Claims are legal disputes. Words determine whether you’re covered or denied.

If your AI can’t correlate:

• Company specific operations with risks and related coverage requirements,

• Professional liability vs. Lender Liability vs. Cyber vs. Media Liability

• What a company needs to consider in regulatory coverage

  
  

…then you’re not just behind. You’re dangerous.

Where Upward Risk Management and Undr AI Come In

At Upward Risk Management, we serve complex clients. We’re not a volume shop. We’re the firm that gets called when things are complicated.

We work with:

• Growth-stage companies with board-level liability

• Fintech and AI companies navigating novel claims

• VCs and GCs who want audit-ready, defense-tested coverage

• Brokers seeking expert partners for E&O, D&O, Cyber, and EPL

That’s why we built Undr AI - to do what generic insurtech tools can’t. It doesn’t just extract terms from policies. It interprets them. Understands them. Flags risks before they become claims.

A Final Word for Founders Building in Insurance

If you're building in this space, ask yourself the following, and feel free to reach out to us.

• Could a top broker rely on your platform without rewriting the outputs?

• Would a seasoned underwriter trust it to explain a coverage tower?

• What is it designed to handle - a $500 BOP or a $15M D&O Side A layer?

If not - slow down.

Talk to brokers. Learn from litigated claims. Build with humility, not just speed.

Because the insurance industry doesn’t need faster clicks — it needs smarter systems.And it won’t trust you unless you earn it.

The Bottom Line

When the risk is small, any broker - or bot - might do. But when it gets complicated?

You need someone who speaks the language, understands the liability, and sees around corners. That’s what we do at Upward Risk Management. And that’s why we built Undr AI.

Upward Risk Management

When expertise is nonnegotiable.