Why Insurance Deserves Better Software

I didn’t start Chestnut because I wanted to build software. I started Chestnut because I was tired of seeing smart, committed people in insurance waste their time fighting bad software.

Most folks outside the industry don’t realize how foundational insurance is. Behind every business expansion, new hire, or home purchase is an insurance product making it possible. Yet the systems underpinning this critical industry are - frankly - embarrassing.

Carriers are running billion-dollar books of business on technology older than some of their producers. What’s worse, the people tasked with driving modernization - CIOs, COOs, distribution leaders - aren’t failing because they lack vision. They’re failing because the available options weren’t built for the complexity they face today.

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Good Enough Is No Longer Good Enough

Legacy platforms have convinced this industry to accept the unacceptable:

• Modernization projects that run 2x over budget and still fail to deliver business value
  
• Commission runs so brittle they require days of manual QA
  
• “Configurable” platforms that still need vendor engineers to make basic updates

That’s not just inefficient. It’s dangerous. It leads to compliance risk, missed payments, frustrated producers, and executive teams flying blind.

If software is the system of record for how you acquire, pay, and retain the producers who grow your business - why settle for anything less than world-class?

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Your People Deserve Better

The truth is: bad software burns out good teams. Every time a producer doesn’t get paid on time, someone in operations spends hours fixing it manually. Every time your comp plan changes mid-cycle, someone in IT scrambles to write a workaround. Every time legal updates your producer contracting language, someone in compliance spends a weekend re-uploading PDFs.

These aren’t edge cases. This is daily life at most carriers.

When we talk to COOs and CIOs, they’re not asking for magic. They’re asking for tools that actually work - for software that respects their workflows, their data, and their people.

That’s what we’re building at Chestnut.

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The Time for Change Is Now

Change in insurance is hard - we get it. But the cost of doing nothing is rising. It’s time for a new generation of insurance infrastructure. Not just modern for the sake of being modern - but better, easier, more insightful for the people who use it every day.

Your software should be a source of competitive advantage, not a liability.

We’d love to show you what that looks like.

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