In your opinion, how much time and effort does messaging & positioning for a product take?

This can really depend on what the product is, how large and complex it is, how well defined the challenges and use cases are. In terms of thinking about messaging and positioning of a product from scratch (in an ideal world), you should think about giving yourself time to go through a few steps: 

1. Market research to understand your target audience, their needs, pain points, and preferences. This often involves customer surveys, 1:1 interviews, focus group, competitor analysis, and analyst reports and marketing trends. This can take anywhere from a few weeks to several months, depending on the depth of research required.

2. Forming your messaging and positioning: Based on step 1, start to formalize your product positioning and messaging, including taglines, elevator pitches, challenges, use cases and benefits. 

3. Testing and refinement: Now that messaging and positioning is formally documented it’s time to start testing it. Test it internally and externally. And try to do a mix of quantitative and qualitative testing. For qualitative - talk to your go-to-market teams and get their feedback, pitch the messaging to analysts and get their early feedback, talk to a few customers and get their feedback. For quantitative - you can test using tools like UserVoice for customer feedback and surveys, and tools for A/B testing your messaging like Optimizely and Google Optimize to name a few.

Once your new messaging is launched, think about how to monitor and optimize that messaging over time as the product evolves which affects the positioning, or its differentiators, or the main challenges it’s trying to solve. A couple of ways I’ve done this in the past is (1) quarterly surveys to customers to help validate our messaging still holds true, (2) quarterly check-ins with analysts to make sure the messaging still resonates with what the market needs, (3) ad-hoc check in with go-to-market teams to get their feedback on how the content (ex: pitch decks) is performing with customers.