Here is one I actually shipped. What happened, what I did, and the stack if you want to run it yourself.

This one started with the market moving under us. The golden era of license-based SaaS pricing was ending, and usage-based models were becoming the expansion engine across the industry. Ours was still a pure per-seat license. That sounds stable until you see the exposure: when revenue is a function of seat count, every contraction at a customer is a contraction in your revenue, with no other lever. A team shrinks, your ARR shrinks with it. You are not pricing the value, you are renting chairs. And underneath it, nearly half our active users sat on the free plan, using the product every week, never paying.

And this was not a tune-up. It was the first pricing and packaging change since the company started: off good, better, best, onto a multi-product, usage-based model. The upside was obvious. So was the downside, which is why half the work was mitigation: sizing the migration impact on customers, and running a tight loop between testing, building, and deploying before anything touched the base.

There were three ways to go: raise the per-seat price and hope, chase the free base with a harder paywall, or repackage around value and redraw the free-to-paid line. The paywall is the lazy read. It punishes the symptom. We fixed the model underneath first, and the conversion followed.

The existing base got handled deliberately, in two moves. The new packaging became leverage for strategic renewals and expansion conversations first. The rest of the base migrated after the new-customer motion was optimized, so the hardest conversations happened with proof in hand.