A two-person startup already uses twenty-eight other tools

When company really starts using Slack it replaces the whole communication system of company, think at the level of replacing the complete Exchange/Outlook system, the whole intra-company email.

It's pretty big deal. And that's why they can charge that level of subscription.

E.g., we use Uberconference for videoconferencing. We thoroughly looked at a bunch of others and chose UC for its functionality, price, and simplicity (every conference gets a simple phone number, no stupid 9-digit code plus pin plus participant id). Six months after signing a 3-year agreement (my bad. rookie mistake) I had to resist my CEO’s insistence that we switch to a different provider when we were courting them as a client. A few month later, sales went out and bought 10 mf’ing Zoom licenses without consulting anyone because some client hadn’t heard of UC and asked if it was the budget solution.

Thank god our new CFO confiscated all the corporate credit cards and moved us to reimbursement with Concur. Of course, he later unilaterally selected NetSuite (for something like $40k a year!) and insisted on coordinating the roll out himself. It has been a months long dumpster fire, but he still won’t give my team admin privileges lest we try to see other’s salaries.

We use a lot of AWS. One of our red-teamers mostly used but occasionally built some of our infrastructure. He left the company last month. Yesterday, salesman from Digital Ocean reached to ask if we are still interested in going forward with the departed colleague’s plan to move all our infrastructure to DO.

So for all you folks stuck in big companies, when you wonder why your IT department is so behind the times and won’t let you use Postgres instead of MariaDB or Gitlab instead of Bitbucket, remember my experience. It’s because no matter how smart you folks are as individuals, in the aggregate you are like toddlers. You dump all your toys on the floor and then chase after some other kid’s shinier toy. Your poor CIO is left cleaning up your mess in the middle of the night after stepping on a Lego brick.

(All that said, my job isn’t bad and my company is way less dysfunctional than most start ups. I get that start ups are chaotic, and the basic nature of my job is to wrangle it.)

This should be very similar to a code review, but seen by CTO, CIO, and CEO (whichever combination is most relevant) so that big unexpected, costly structural changes don't cost long term disfunction and pain.

For example, I used to use the MixPanel free plan in a project and went over the limit and suddenly the plan cost around a thousand dollars per year.