How do you quantifiably test messaging? Rather than relying on anecdotes from the revenue organization?

This is a great question! Given messaging is such a subjective topic - it's super important to quantifiably test and iterate on it to ensure it lands well in the market. Here's a few strategies and tactics you can use to quantifably test it: 

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 qualitative tests where you test specific aspects of your pitch and differentiated value or quantitative tests of words or descriptors you use.

2. Solicit early feedback from Sales and Customer support teams - We’ve recently done this super effectively at Hubspot, by essentially recording a Loom video of our pitch (keep it under 5-7 minutes) and following that up with a Google form with specific questions to solicit sales and customer success feedback on the pitch, differentiated value, use cases, imagery used etc. 

3. Leverage platforms and tools such as Wynter - This has been another effective platform we’ve used to test messaging effectiveness and gain specific feedback on what resonates and doesnt with your prospective buyers. Wynter allows you to crowdsource and get real-time feedback from your target customers. 

4. A/B test on your website, ad copy, social copy, search copy - these are simple and effective ways to test a couple of different messaging options with your prospects in real-time to see what resonates most.

5. Email test your messaging to prospects - This is a tactic you can easily use to test different subject lines, body copy, CTA’s to see what resonates most.

My first question is: what's the reason for not relying on your revenue org? Is there a lack of trust, challenges with prioritization, or something else? The best, most differentiated positioning means nothing if it's not being used throughout the customer journey – and since the majority of marketing orgs are focused on driving leads to a sales team, that messaging better be consistent at every stage of the marketing funnel. I view our sales partners as essential in building, validating, and activating our messaging. 

Since much of the intel we gain from sales teams is rooted in the present challenges our target audience is facing, I tend to work closely with them to identify key pain points, then validate with new and existing user research (both in-house and sourced with third parties), broad customer surveys (key trends based by audience), and by talking to customers any opportunity I have. To that end, I'll often volunteer to present a product pitch, volunteer for booth duty, or present our roadmap, just to have face-time with customers; we're providing direct value, so folks rarely object when I ask a few additional, discovery questions, or drop-in new messaging just to observe their reactions. 

The best messaging, though, doesn't just address the current problem, but future problems (and in an economic downturn, economic opportunities) that we are best positioned to address. So, vision-building is often more of a conversation and ideation exercise with my product stakeholders. Simply, intel from sales/customers is great for messaging that gets heads nodding, and the product vision conversations are what I use to get people excited about the future. Together, that's the peanut butter and chocolate of messaging. 

While this question was specifically about quant tools, it's essential to start with that qual research. Some really talented UX partners taught me that qualitative data is essential before building out quantitative research – I treat messaging the same way. 

On the quant side, here are a few things I've seen work:

• Message testing with friendly customers/customer-facing teams (either via an ad hoc or existing VOC community – ask them for quant and qual feedback in exchange for swag, donations to a cause, or access to new features)
• Painted door exercises (A/B test landing pages and ad copy with variations of content to measure CVR)
• Sales training & correlative win/loss rate (train teams in new messaging and observe changes in win/loss and customer segments over time using tools like Gong)

There are a few ways you can validate your messaging: 

• I like to start by doing a customer listening tour. Spend some time getting to know your target customer and pay close attention to the way that they are describing their process and pain points. When you unveil your final messaging, it's important that you're speaking to your audience in the words that they use to ensure that your message resonates. 
• I also like to look at market trends and SEO insights to help inform the direction. I'll often spend time on third party review sites like G2 to understand how they're defining categories and features. It's also helpful to comb reviews of your own product and your competitors to again understand how the market is tending to describe certain features and functionality. It's always helpful to root yourself in what your audience already knows, how they're talking about things, and how they're already searching for things in their own words. 
• When it comes to true messaging, like the actual six words that are going to appear in big bold leaders at the top of your website, you can conduct user tests to understand how this message resonates. This takes time and resources, so I'd only recommend this for really big projects, like a total repositioning of your product vs. a small feature launch. Have your team mock up your top 2-3 messaging variations and see how the audience responds through guided interviews. Alternatively, you can incorporate message testing into surveys or run A/B test on paid ads to see what converts. 

You can use a slew of KPIs to measure effectiveness.

1. Conversion rate: the percentage of people who take a desired action, such as making a purchase or filling out a form, after being exposed to the messaging.
2. Click-through rate: the percentage of people who click on a link or call-to-action in the messaging.
3. Engagement rate: the percentage of people who interact with the messaging, such as liking, commenting, or sharing it on social media.
4. Customer satisfaction: the level of satisfaction and loyalty expressed by customers who have interacted with the messaging and product.
5. Brand awareness: the percentage of people who are aware of and recognize the brand and its messaging.
6. Sales revenue: the amount of money generated by the product as a result of the messaging.
7. Net promoter score: the likelihood of customers recommending the product to others based on their experience with the messaging.

Use a messaging evaluation framework like Message Layers.

The way to improve messaging is to break it down into five components, measure, and work on each separately:

↑ Clarity (I get it)

↑ Relevance (it’s for me, helps with my specific challenges)

↑ Value (I want the promises)

↑ Differentiation (I get how this is different)

↓ Friction (resistance, doubts, anxieties)

When you conduct back-to-back message testing, you get to see how your copy scores on all of the above.

You also see the improvements for each one of those elements in every iteration and notice the changes in your sign-up rate, lead quality, and volume.

If you don't want to do this manually, a tool like Wynter will automate it for you.

In addition to great advice in other answers, there are a few other things to consider:

• Most message testing is artificial. People are asked to carefully read and ponder the message before giving feedback. This isn't how people process messages in the real world. There are techniques that can be get at "System 1 thinking" - the automatic and near instantaneous process people will use when encountering your messaging in the wild. This can be as simple as only displaying the message for a few seconds before taking it away. The careful reading is also useful, but later.

• Get feedback on critical dimensions. Ask what brands come to mind when they read the message - see if yours is in the list. Test if the messaging is differentiated, or sounds like what everyone is saying. Is it motivating. Is it memorable (check what they remember later in the conversation). Is it credible? Is it relevant?

• Pit the messaging against competitors. Show people a mix of your messaging and competitors. Real customers will be looking at messaging from a variety of companies. Does yours win out?

All of these things can be rated as on quantitative scales. Hope this helps.