“When you're solving new problems, that's a great time to think about that as well. If you create a really big new feature that solves a new job to be done or solves an existing job to be done in a much better way, that's a great opportunity to introduce that higher price tier… it's a lot easier than just raising the price across the board.”

Launch a new tier alongside a new feature — not as a standalone price hike

Bundling a price increase with a meaningful new capability reframes the change as added value rather than a take. Existing subscribers self-select up to the higher tier because they're paying for the new thing, not absorbing a hike. Time price changes to coincide with substantive feature launches.