In your Product Management career, what have been some of the most challenging applications to support?

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I’ve worked on 2 different products that were built on proprietary internal architecture from 20+ years ago that were a nightmare to work on. Lots of dependencies, lots of knowledge silos, and little desire from other teams to help you solve your solution. In both cases, prototyping with newer architecture (AWS cloud instance) allowed us to prove the concept and strategically integrate over time rather than having to rely on the existing tech stack.

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Were there times you considered the “battle” wasn’t worth it and you’d like a change of scenery? I’m feeling that way now and this current economy makes it harder to leave.

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Those I had to integrate with government technology and systems that required me to implement what would typically be non-necessary middleware and conversion layers.

The data may have one leading zero, two leading zeros, or no leading zeros as one example and updates had unpredictable behavior. These were just the types of anomalies that routinely came up.

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Yeah I mean it was a new vertical so it had to be explained what it was, why we needed to do it, and then why we needed additional infosec as well.

The bigger headaches are the unexpected fire fights from data issues from the various state and federal systems and having to explain it on wbr and mbr’s because it creates the impression that it was our tech that was buggy.

It was application called "the boss".

Software is easy to handle. It the personality of insecure bosses when overshadowed by more talented reporters, that's the most challenging situation to be in. It's like walking on eggshells around them.

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