Free trials are tricky. If your product is good, then you want as many people to try it as possible. On the other hand, although some percentage of the people who try the product will convert to paying customers, many won’t. You can fool yourself into thinking more people are interested in your product than actually are. You won’t know whether you have a viable product or not until the trials are over.
With Hyperion, both the benefits and drawbacks were magnified. My customers are non-profits with tight budgets and I knew many purchases required approval from a board. Requiring a champion to go in front of a board and argue for an increase in the budget would be a major barrier to adoption.
On the other hand, because it was a software product used for a yearly event, offering a free trial would mean postponing income for a long time.
That said, because of the high-risk nature of the use-case, and because adopting the software would mean changing process and training hundreds of volunteers, I knew that if they used it for the first year it would be a significant sign of interest (and I would have some reason to think they would convert).
All in all, I decided to make it free for the first year. I won’t really know how many customers will end up converting until the middle of next year, but I’m optimistic.