Reflecting on My Technology Leadership Journey and Job Search Challenges

I've been in technology leadership roles at the Director level for about 10 years, and I'm starting to feel like I've been misled by two different employers in similar ways. Recently, I've been searching for a new job because I believe it's easier to find new opportunities while still employed. As I've reviewed VP-level job descriptions, I've noticed that they align closely with what I've been doing in my previous roles—about 80% of the responsibilities match. The only differences seem to be regular meetings with the C-suite and board, which I have had some exposure to, and top-level decisions where my input was significant. To make matters worse, I recently checked the LinkedIn profile of a former CIO I reported to, and it reads like a summary of my daily responsibilities at that company. I had previously asked the CEO if I would be considered for the CIO position when they were hiring, and he told me no without providing a reason. At the time, I assumed it was due to a lack of experience, but now I'm starting to doubt that explanation.

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