The Acme of Tech Cluelessness
If I've learned anything in three decades working with enterprise tech, it's this:
The older the organization, the worse its systems are likely to be.
Call it Simonβs First Law of Enterprise Systems. Since I like graphs:

Is the law absolute? Of course not. I've seen small organizations and startups immediately screw up their new systems. Plenty of larger ones run tight ships. On balance, though, Simon's First Law holds up. (Why New Systems Fail contains plenty of studies to this effect.)
Car Insurance Chaos
Case in point: I recently switched car insurance companies. We'll call the new one ABC here. (Fun fact: The real outfit set up shop in 1864.)
After pulling the trigger, the following happened over the next week:
- ABC kept sending me updates on my initial quoteβagain, after I purchased the policy. (I can only imagine what type of antiquated CRM it's running.)
- I could not access my new policy on either ABC's website or in its primite iOS app. Customer service advised me that its systems (plural) weren't working for new customers. You know, the ones most likely to cut bait.
- Making matters worse, ABC's iPhone app didn't support Apple Wallet, a tool that arrived in 2012. Save a photo like nervously try to find it when pulled over like it's 2007.
- To track my mileage and safe-driver discount, I would have to regularly snap photos of my car's odometer and send them to ABC. (By contrast, consider my previous insurance provider, Lemonade. It let me plug a simple dongle into my automobile's OBD-II port. No photos and uploads necessary.)
Within a week, I canceled my coverage and returned to Geico. True to form, ABC sent me a reminder for my active quote the next day. You just can't make this stuff up. (Maybe it sent more, but I added some code to my sophisticated Fastmail filters.)

Simon Says: I dodged a bullet.
In a way, I'm happy that I experienced this level of tech ineptitude with ABC right out of the gate. Things would have been much worse if another car had hit mine or vice versa months or years down the road.
Give ABC credit for lasting so long. If it doesn't fix its enterprise systems and mobile app soon, though, its days as a viable independent entity are numbered.

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