When looking at license options, there are a few things to consider.
First, how many people will use the system and what features do you expect them to use? Sometimes licensing is different based on both number of users and the features of the software. So for instance, you may have five superusers and 10 regular users, which would force you into two separate bundles of software.
The next thing to look at once you determine the number of users is the frequency of their system usage. If you have highly transient employees for instance, it may be advantageous to look into some shared licenses. In this case, you may have four or five infrequent users sharing a license.
Beyond that, you need to look over the period of expected usage and the projected employee churn rate. If the company is about to ramp up resources or plans to have a large layoff, then you need to see what this fluctuation will do to your user agreements. You don't want to over provision licenses, and you don't want to under provision -- unless the licenses are easy to scale up or down. In general, with bulk deals, scaling is in lots of 50 to 100, as opposed to one at a time.
Finally, when you have all that information on hand, it really boils down to dollars and cents. If you can buy a bulk pack of licenses and you feel you will consume the majority of them, it may be fiscally beneficial to look at bulk licensing. If you don't believe you will hit that mark -- either today or in the near future -- you should calculate the per user license to see where the break-even mark may be.
For example, suppose bulk licensing was $15,000 for up to 100 users, while individual licenses were $185 each. If you needed 85 licenses, then the bulk option would be less expensive. This would also mean that there are 15 seats available for potential hires to use over the term of the license.
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