[toyg]

As somebody who has built quite a few of these internal extensions through the years, technical hurdles were never the problem.

The problem was to persuade managers that they were worth the effort, persuade workers that I wouldn’t “screw up” their preciously-pristine browser, and persuade IT not to use their “UNAUTHORIZED SOFTWARE!!11!” flamethrower. In short, exclusively people-problems.

Keep that in mind, in terms of who you need to sell this to.

[kkevv]

Haha, thank you for sharing your insight!

How did you push through all the people-problems? Was the productivity gained from the extensions the angle you pushed?

[toyg]

Obviously, and it typically requires triangulating alliances (users & managers vs IT, or users & IT vs managers, occasionally IT & managers vs users but that's often a symptom the tool is not good).

One big issue most managers care about, is long-term maintainability. When you sell this, you should probably advise customers to have more than one person skilled up and responsible for maintaining the resulting tools. I was often bounced because "once you leave, nobody will know how to fix this" (which is fair, and happened more often than not). Making it easy to share projects is key.

[kkevv]

Gotcha, thank you so much for the advice. Maintainability, especially with something uncommon like a Chrome Extension, must seem really sticky.