Bohemian Coding, you asked for our thoughts on Sketch’s new pricing and versioning plan, below are mine. There were some gaps in your outline, so I’ve made some assumptions. If any are incorrect, I apologize.
Paying $99 each year instead of $99 every couple years after a major release, is not a big deal. As Sketch has grown it’s feature set and reliability has expanded to the point where it now feels “cheap”. So I’m cool with paying a little more for a better product. But be honest about it. It has nothing to do with fairness to users who bought a 3.8 release in comparison to those that bought a 3.0. The 3.0 users paid more money for a lesser product. It all evens out. What it’s really about is making more money. And that’s fine. As I said, I think your product is currently underpriced.
I hate subscription pricing models, doesn’t matter whether it’s Spotify, Adobe, or Verizon. They are decidedly anti-user. It saddens me that you’re dipping your toes into this path, but I’ll reserve condemnation until you fully cross over. But unlike Adobe, who bricks your software the second you stop paying for your subscription, Sketch will let you keep using the version you’ve purchased in perpetuity. It’s a quasi-subscription. Except it’s not. There’s one giant problem, and that’s that any file that is created in a new version is unusable. So if I get a file from a friend, or download the new iOS GUI Kit and it’s a Sketch 4.4 file, but I only have Sketch 4.3, that file is worthless. And eliminating the concept of major releases will make this more difficult. For this path forward to be a smooth one, you need to resolve backward compatibility issues, and continue to differentiate yourself from everything people despise about Adobe.
Declining User Base
I’ve worked with many developers that have purchased Sketch because at it’s current price point it’s economical for them to be able to view layered files as a part of their workflow. This will cease to be the case with your new pricing structure.
A word of caution, this new model will drastically alter the expectations placed on Sketch and Bohemian Coding. Historically there has been great pressure, as you noted, to pool major features into major release to encourage users to upgrade and new users to sign up. Now the pressure will be in 12-month cycles. If you’re not releasing major features within that rolling window then you will face potentially large group of users who need to renew their license/quasi-subscription without feeling like the received worthy value from their previous one. Communication will become even more important now. A public roadmap, as some have suggested, may be a good place to start.