Converting free trials better

the freemium model is such a powerful go-to market strategy. slack's infamous success story rides on the back of their 30% conversion from free-to-paid. check out this deep-dive here: https://dgajsek.com/growth-study-slack/.

there is such a fine line between giving away too much and not giving away enough. usage data, success milestones, and ultimately desired outcomes help software companies understand the moving target to optimize conversion from free to paid.

for those in the IH community that offer free trials or free versions of your product, how have you discovered that line between maximum conversion and consistent value? what specific usage metrics do you monitor? what specific success milestones do you track? and how do you track it?