How can a SaaS company test pricing without ending up with a large group of customers that are on strange plans?
Don’t worry about it.
Assuming you are growing very quickly on a percentage basis (i.e., it’s fairly early) … your pricing today really doesn’t matter much. A few years out, these customers will only account for a tiny % of your revenue.
But you do want to improve your pricing for all go-forward deals.
So tweak and experiment away. Don’t worry if you end up with 132 different pricing plans in your first 264 customers. Yes, that’s annoying. But what really matters is driving deal sizes up for the next 264,000 customers.
We obsess way too much about pricing “at the moment”, and not enough about where pricing and deal sizes will take us.
Take the time to run the right ongoing experiments, even at the risk of a little pricing plan nuttiness in the present.