Do you prioritize messaging your freemium product or your paid product and why?

1. I’d actually prioritize messaging your overall product and what your vision is for the full functionality of your product. I say this mostly to point out that having messaging that’s wildly different between plans usually means you need an overall messaging framework first.
2. That said, I always think you should be messaging the full value of your product when it’s at it’s most powerful, and encourage prospective and current customers to use the best version of your product. When you show the power and value provided in your paid product as your overall message, you’re putting your best foot forward.

I think it's important to start with your business goals... In general, the goal of a freemium model is to grow your user base and then engage those users to upgrade to a paid version of your product. But before you even get started down that road, you need to have clear understanding of the value of your paid product and each of the features for your core personas (what do my customers care about, what problems do we solve, what additional value do we deliver that makes them feel like a superhero at work, etc.). 

I would always prioritize your paid product messaging and positioning first - get that to a place where it's really strong and clearly articulates the value. Then start building your freemium messaging as an offshoot of that core messaging. With freemium, you have 3 major goals - 1) making sure that the value is clear so that people will want to take the time to try it, 2) making sure you have clear differentiation between the free and paid versions of your product and 3) having a clear upgrade path between the two products. Depending on your business model, that journey may be a couple months or as short as 14-30 days. Either way, it's important that you have a consistent brand experience (and messaging!) from freemium sign-up to paid renewal.