What indicators should we look out for to know to hit pause to test messaging? (many launches go to quickly to test messaging before it hits market)

Agreed that often in the race to get a product to market, teams will put their best messaging idea forth, run it out for a quick test and then launch. I think there are a few ways to check that you’re on the right path or if pausing is required.

1. Internal comprehension - at least in the case of Upwork we’re lucky that we collaborate with many freelancers internally. So when they see the messaging and find it confusing or have a lot of questions about a launch that are clearly not obvious through the product or available messaging, that’s a good time to pause. So use your internal folks to give you a read on potential issues with the messaging.
2. Target audience comprehension - when you launch, you may hear feedback from your most vocal sales reps and the loudest voices in a community forum. That said, these may not be your target audience. If however, you hear negative or confused feedback from the very people you designed the messaging for, it’s time to pause and circle back with this audience to understand what’s going on and how you can bring more clarity.
3. Unintended audience comprehension - a nuance to the point above is that you may have customers outside of your target for whom this feature isn’t valuable but due to messaging confusion you feel are at risk for churn or reduced engagement. In that case, pausing and refining your messaging for these secondary audiences can be important.

Getting messaging right is hard. We tend to get biased on our own messaging and copy after staring at versions of it for hours and days. It is important to get objective pulse checks from people closely resembling your target audience.

If the message tends to focus heavily on features and the product’s benefits vs. the customer outcomes, that’s a sign of missing the mark. I always say the story should not be about what the product can do for you, but about what you can do with the product. The latter is about empowerment - which is what your customer likely wants to see and hear.

This is one of my favorite topics, and one I'm going to be writing an article on, so I'm glad to see you asked it here! A big red flag as a PMM is when your customer base is incredibly polarized in the satisfaction of a feature or product. When you have half of your customers who absolutely love it, and the other half absolutely hate it, there is a really good chance that the messaging/positioning isn't consistent. The people that hate it, were probably "sold" something that the product doesn't actually do - so when they go to implement, they're unhappy. Another good indicator of this, is when your PM has a ton of feature requests that goes against the intention/purpose of the product. When you start to see things like this, time to hit pause and dig deeper. Find out how it's being positioned by Demand Gen, Sales, and Services. Look at the support tickets and feature requests for things that are really out of scope. Talk to unhappy customers and find out what problem they were hoping to solve when they purchased your product. Then talk to your really happy customers, and find out what problems they were trying to solve when they bought your product.  

Then, when you have all of that data, find the common ground. Are your unhappy customers mostly larger companies? European companies? Legacy development companies? Financial institutes? etc etc... and you'll start to narrow down the target, positioning, and messaging issues. Then it's time to re-align your messaging around 1) what the buyer's problems are that need to be solved and 2) the problems that your product ACTUALLY solves for. Then re-enable your sales and marketing, to leverage this new messaging.  

You'll know it's working when renewal rates increase, support tickets decrease, and most importantly out-of-scope feature requests dissapear. And if you're not watching all of these things for your product, you should be - Product Marketing is much more than just writing headlines :)