Wanted to write in support of annual discounting.

Most people who need WordPress-related software for a business purpose are going to buy it when the need it for a project, not wait around until the one time during the year they can get a discount.

OTOH, some people who want to purchase the products for their own use find the prices too high to be comfortable for their budget and would not normally buy, but are willing to buy when discounted.

In other words, I believe the discounts target a market that generally differs from the market that buys during the rest of the year. If the discounts are not offered, then only the latter are captured as customers instead of capturing both.

Of course there may be other reasons to not want to capture the discount-seeker market; i.e. they may have higher support burden, but offering infrequent discounts is not necessarily problematic simply because of the discount's affect on margins. Sure there might be crossover cannibalization, but I'd be willing to bet the crossover is minimal.

All that said, mine is just an different opinion on the matter and the only way to know for sure is to test. But testing is hard and most vendors in the WordPress space don't have the resources nor the volume to test properly, and even so it would hard to test without at least one year of discounting to evaluation.

So, I make this counterpoint for those who are trying to decided on discounting to give them more than one perspective.

P.S. I have no dog in this hunt today. I have not done any WordPress work in a while so I am not planning to make any 3rd party purchases for the foreseeable future, and certainly not any Black Friday deals.