- Sign up for free or with a credit card, but you'll run into problems (or at the very least friction/complications) if you end up trying to use if you something serious
- Speak to a salesperson and have your CFO sign the company up for a long-term strategic partnership.
The examples that you gave are less clear-cut though. Trello Business is $12.50 per month, and supports Google Apps SSO. Trello Enterprise supports general SSO, and costs $20.83 per month. Slack pricing is $6.67/mo for Standard, and $12.50/mo for Plus with SSO. None of these are costs that should really make or break the profitability of a company; considering that the business is using them to generate revenue or to reduce its expenses, how do they compare to other things like property/facilities expenses and employee salaries/benefits?