AMA: HubSpot Former VP of Product and Solutions Marketing, Vidya Drego on Messaging

That's a tough call. What we've found recently is that as we've adapted our messaging for an enterprise audience, it's resonated less with small businesses. Some companies choose to vary their messaging by audience size (e.g. Shopify) others have one-size-fits-all messaging regardless of size. I think another option is somewhere in between where there are different reasons to believe, proofs and sometimes even value propositions depending on the size of the prospect or customer (but with other aspects of the messaging ladder remaining the same). I think it's difficult for messaging to work for all size audiences though so if the differences are extreme, it's probably wise to force a strategic decision about what audience to focus on before trying to write messaging to work for everyone.

As I mentioned before, I always try to align positioning to where the product is going and where the company wants to be. Messaging can then roll out in several phases until it realizes this ideal positioning. Ideally, you have an understanding from research of what your prospects and customers believe are the key features and reasons to believe that deliver on your ideal value prop. With that, you can determine how often to adjust messaging as you evolve your product offering.

I truly believe messaging should be a living, breathing thing that gets updated periodically. How often though can be challenging. It's often not feasible to update it at every product launch or, if decision making takes a long time, it can be tedious to update frequently. This is where I think aligning on year or multi-year positioning that reflects the future state of the product roadmap can be helpful. Then, you can think of messaging as evolving in several steps until you realize that ultimate value. If your positioning anchors to where the roadmap is going, then you can decide in advance at what point you've delivered enough of the value to update the messaging.

Positioning and messaging both help you explain the value you deliver. I've always thought of positioning as something that lives internally within a company to help the organization contextualize their product or service within their category. It's the strategy by which you choose to communicate your value. The messaging is the words they use to explain this to the outside world. The two are very related and in some companies with a mature offering, they may be mostly the same. For companies that are earlier stage, your messaging may reflect the immediate nature of where you are while your positioning captures where you plan to go.

We use a messaging ladder (a slightly customized version of many i've seen online) but are increasingly using a broader framework to connect our messaging to the buyer journey. The framework we use to structure the messaging doesn't dictate how often we update the messaging. For this, we try to anchor our positioning on our product vision at least 1 year out and figure out evolutions to our messaging that help us realize that long-term positioning.

It's pretty difficult to get a straightforward read on the effectiveness of your messaging and positioning but there are a few things you can do to ensure your messaging is more likely to succeed. 1) During the process of creating the messaging, work with your market research team to test aspects of the messaging with prospects and customers. This can be both quantitative test of words or descriptors you use as well as qualitative tests where you actually test aspects of a pitch with customer. 2) Get input early and often from your sales, customer success, and support teams. 3) Use A/B testing to evalute how the messaging resonates on your website, search, social copy. Once you've created the messaging, you can use your channel metrics to track how well it's resonating but give it time. Any change of messaging takes a while to take hold with the audience (be it sales or customers) so don't be in a rush to make an update just because you see metrics dip initially.