Great post and I totally agree. I recently talked to my financial advisor about my current company and we went through all the numbers for various pricing scenarios (of a public offering) over the next 4-6 year, at various valuations. From his point of view, he encourages me to stay the course - quite the opposite from most of the tech friends I know (most usually don't stick around after a few years).
On a side note, I haven't used it in a long time, but why all the hate on Jira? I mean, I remember it does everything including making my breakfast for me, but is it really that bad? I don't remember it being that bad, but maybe others would like to chime in on why they like/dislike it?
JIRA is what you make of it. My comment is that it requires a ton of gardening to keep it useful. You probably need 1 person for every 5-10 devs who has JIRA-wrangling as a primary responsibility that eats a significant chunk of their time. Part of this is the nature of project management, but part of it is that JIRA's workflows for basic tasks like "close as duplicate" or "do this action on all issues linked to issue X" are terrible and require way too many clicks. In shops that don't properly allocate people to this task, it's extra debt that just piles up and becomes a mess, so I could definitely picture some of the hate being as a result of those experiences.
The author may also be using "JIRA" as a proxy for a heavily pre-planned waterfall culture with a big emphasis on time tracking, doing what you're told, fake-metrics success theatre, etc. (cf. https://hackernoon.com/12-signs-youre-working-in-a-feature-f...)
I hate it because it feels incredibly crusty. Nothing seems to update without hitting F5, there's annoying amount of jargon and poorly named fields everywhere, and in my company it's also tied into everything from client billing to asset management, presumably because it's sold as something that does everything including breakfast, and all that noise seems to permeate into every ticket type (I can't search for a ticket type or field anymore, there are over 400 types so the autocomplete is useless, I just ask PMs to make them.)
I'd love to see us move to Phabricator (https://www.phacility.com/phabricator/) but the problem is it's developer oriented and there's already man-years invested in that Jira monstrosity, it'd be a tough sell and probably just end with us spread out accross both...
JIRA isn't a tracker, it's a tracker construction kit.
If you put the legos together right, it's great. If you build a turd with it, it's gonna suck. That aside, it's slow and gets in your way a lot. IMO it's the way to go though.
JIRA is not that bad. It was pretty stagnant for a while but they've been improving it. I think JIRA is an invaluable knowledge capture tool, particularly when you're tracking down a difficult root cause and you want to keep a bunch of people in the loop.
Jira is not fun. The things about it that make it suck is that it's used for employee time tracking in a round about way. Most teams can get by on a simple issue tracker (like github issues or buganizer), but once you get bigger, you need something that manages everything like JIRA, which eventually becomes part of you justifying your existence at a big company.
I'd highly recommend checking out alternatives. The one that impressed me (for a particular situation) the most recently is Clubhouse. Compare based on your needs. Enterprise needs with established products are not the same as a startup, as you know or will soon.
Yes, some companies prefer / require / demand self-hosted installations. Some do it for logical, financially responsible reasons too.
Numbers-wise (measured on a 'per company' basis), I would tend to disagree with the 'most' part of your sentence. Aren't there are many more 'smaller' companies happy to use hosted services as compared with companies that require self-hosted ones?
On a side note, I haven't used it in a long time, but why all the hate on Jira? I mean, I remember it does everything including making my breakfast for me, but is it really that bad? I don't remember it being that bad, but maybe others would like to chime in on why they like/dislike it?