First, amazing to see the growth of building something people want, largely self-directed and self-funded.
Pricing, after naming in coding is a really slippery concept.
1) You could draw a line in the sand and move new feature into paid plans. This might be tough.
2) If you move enterprise type features (sso, custom domains, branding) into an enterprise “call us” plan it will not be suprising. Many companies buy software this way.
Generally speaking, it will be helpful to discover your pricing gates where people can make a decision without an approval. Usually that’s $250/mo, $500/mo, all the way up to $5k depending on the industry and size of client.
The path ahead is to test one hypothesis of pricing, or many. You could make one interpretation of how to reorganize your feature to plans, to realize it needs ongoing experimentation. It would not be unusual to adjust your plans more than a few times.
3) My best advice is to recommend a flexible pricing experiment engine, I’m a fan of using/implementing a feature flag management system in combination with a subscription management system. It can built in grandfathering (good karma and referrals), but also provide data on every type of plan you’ve tried.
We ended up being able to run multiple pricing structures of the same features to address much more of the product. It became a differentiator because competitors could not bill as discretely and effectively.
I have a few (dozen) pricing articles I’d be happy to email your way. I’d have to dig them up and publish them to a link for you otherwise I’d share them now.
Relevant background: I bootstrapped an online learning system which also took off due to solving user problems and not copying others.
Over time, competitors copied more and more of what we built but we were able to accidentally delay it for several years.. the best thing we did was talk to customer segments liberally but avoid startup hype circles and not pitching to people who weren’t potential customers or allies. For better or worse, startup circles are full of folks looking to poorly implement an idea or space they didn’t understand and in some industries existing competitors they were building to maintain a desktop centric past.
If you are working in a historically slowly evolving area (as I am in EdTech), many people look to others on where to go, which is very odd.
Happy to connect and chat offline, my email is in my profile.