Not to say this would have worked at your company, and not to say it's perfect, but I think the "HACK" of the bottom-up approach for software like JIRA or others is that it is priced in a way where you can get your team at a company using it and showing demonstrable value from using it on a free or very low-cost (AKA your personal credit card) tier.
Then, when you go to make it official, you have much more power in the negotiation.
If it's working well, making the "shadow IT" SaaS tool an official purchase typically goes:
Team Lead: Everyone is using this tool, we're about to go above the free tier and need to purchase it.
IT/Finance: You should have gone through the process, you need to fill out these forms.
VP/CEO (to IT/Finance, seeing value of tool): Just get it done
I think maybe I wasnt clear. No one tried to keep us from licensing anything. Pretty much any solution was fine with then assuming it wasn't a security nightmare.
> Just get it done
Getting it done is a process heavy, minimum 4 month process because of purchasing rules. That's the problem I'm calling out.
Whether it's IT or Finance (purchasing rules), CEO/VP have the power to force them to make an exception or change their process if there's a clear business benefit.
I'm talking about 10K+ global employee companies. No VP wants to listen to my problem licensing Jira. And prices changes like that happen on the scale of years.
Exactly. Then taking it a step further. GP at VC firm makes the round at their "portfolio" companies and see your product on every screen, or hearing about your product from every team they go to, and then wanting to speak with you because clearly someone is doing something right.
Then, when you go to make it official, you have much more power in the negotiation.
If it's working well, making the "shadow IT" SaaS tool an official purchase typically goes:
Team Lead: Everyone is using this tool, we're about to go above the free tier and need to purchase it.
IT/Finance: You should have gone through the process, you need to fill out these forms.
VP/CEO (to IT/Finance, seeing value of tool): Just get it done