As part of my experience, as CEO & part of Executive Management, one of the key challenges that we faced is around technology and value.
Sharing one of my experiences with you: As CEO of a Startup Motor Insurance Co (100% Online)
Getting directly into the context: An IT System was chosen before I started my tenure there. What started as a 6-month implementation for one LOB with USD 2M budget turned out to be 18-month project & USD 10M actuals - end of it, we were not happy campers.
As head of the Company, I did not know a lot about IT & it's working. I also did not know to whom to turn to for right advice and support. We were a start-up company, with very lean team. Targeting the sky - we were in a rush to get the IT going. It was very crucial to our starting & running of the business. We wanted to empower the customers to do everything online! (shop, buy, pay, report and what not!). And be The Swiss Geico......
We encountered a lot of issues, and we did some amends in the journey - kind of quick fixes - thinking that they would somehow take care of the issues & get us back on track. We did not understand the magnitude/gravity of the twists & turns to reach destination! It felt - we were at the bottom of the pit, even the nearest was not in sight!
So, I started thinking - if we were going this wrong, there must be something wrong with the way we have approached this whole thing - technology.
In hindsight, I realize that we have not asked ourselves any questions before embarking on the journey and during the course too. We did not even know that we have to ask the questions. A Project Manager was all we had - we left it to him to deal with IT. We wanted results and no headache.

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