7 Principles of Great Messaging

If you’re familiar with enterprise GTM, you know all too well that your value proposition ultimately boils down to saving your customers time and money, or reducing risk. The challenge lies in saying the right words, at the right level of depth, to the right people—in convincing your target audience that you deeply understand their pain and can uniquely solve their problems. The framework is simple: you need a clear positioning statement, a well defined target audience, your value pillars and your supporting proof points. And of course your messaging doc should be a living breathing document that evolves over time.?

I’ve had the privilege of crafting category-defining messaging from scratch four times in my career as a tech executive. My first was back in 2010, with VMware vSphere. At the time, vSphere was the market leader in virtualization, a $2.5B product growing 40% year over year. I was responsible for a major messaging shift: the value prop had to evolve from server consolidation to business critical apps in order to expand our footprint in existing accounts. And we nailed it. My next big messaging challenge was launching VMware’s VSAN, which marked VMware's entry into storage and became the fastest-growing new product at the company, exceeding revenue goals in initial years and eventually growing into a $4B product.?

While big companies have massive resources you can orchestrate, startups are a different ball game. At a startup, your words have to stand on their own. At both Ravello Systems (acquired by Oracle) and Rockset (acquired by OpenAI), my goal was to achieve product-market fit as quickly as possible, then scale from there. We created massive inbound demand that was driven primarily by great content and messaging. How do you define your target audience, position the company, and craft messaging that resonates with early users and adapts as the product goes mainstream?

In my early years, I was lucky to learn from veterans like Bogomil Balkansky . But even as I honed my messaging intuition through countless customer conversations, I realized one thing: coaching early-career PMMs is harder than it looks. I found it challenging to give actionable feedback on messaging that missed the mark and wondered how to help my team build their own messaging muscle. I had to step back and articulate my process, principles, and frameworks for effective messaging to help my team elevate their craft. Over the past few months, I’ve had many CEOs ask me about the method behind the madness of great messaging. So I decided to share 7 principles that I’ve personally used to take messaging from good to great.?

1. Own Conversion Metrics in the Sales Funnel

Why do some PMMs get caught up in “ivory tower” messaging that doesn’t resonate internally or externally? Why do some executives have a better pulse on the market and land on the right messages intuitively? I’ve found that great messaging comes from being goal-oriented and having clarity on your messaging's impact. When we hold PMs accountable for product adoption it inspires them to create better roadmaps, but what do we hold PMMs accountable for?

Revenue and pipeline are on every marketing team's list of key metrics but the best PMMs craft messaging with sales conversions in mind. This empowers them to collaborate closely with sales and analyze the impact of their messaging at every funnel stage—from who you see in the first meetings to POC win rates and how fast you land and expand.

At Oracle, I worked on AI messaging back in 2016. We had lots of great value props but the elephant in the room was that we didn't have a great solution for unstructured data back then. Is it a product issue or a messaging issue? Unless you tackle it head on, it will show up as a major drag in sales funnel.

At Rockset, we moved away from competing with warehouses like Snowflake and focused more squarely on displacing Elasticsearch for real-time analytics. It would have been so much easier to fill the top of the funnel with warehouse displacement deals due to the sheer volume in that market. But we quickly realized which deals we were better positioned to win and narrowed our messaging focus to achieve PMF faster.?

2. Create OODA Loops

I learned about OODA loops (Observe, Orient, Decide, Act) some time ago, and it’s been great for for messaging under ambiguity. It means quickly collecting and sharing learnings and aligning directionally with key stakeholders early and often.

• Customers - What are their problems? How does the pain manifest? How do they describe it? What triggers it? What do they Google when they are in the pain cycle??
• Competitors and partners - How are competitors approaching this problem? Are there other alternative approaches that do not involve our direct competitors? How are we differentiated? Why should our partners care??
• Executives - What is the long term vision? Where are we headed with this? What are the core values and beliefs that are implicitly baked into how we approach this problem??
• PM/Engg - What is the technical solution? What are the trade-offs? What are the proof points? Why is it compelling? What is the future roadmap??
• Sales -What are the drivers and drags? What friction are they seeing? What objections are they struggling with? Where are the bottlenecks??

My PMM team at Rockset would binge-watch sales Gong calls and add commentary in slack to discuss the aha moments. Or they would interview potential target users (yes, we scoured the internet and cold called these research subjects) and share new insights internally in bite-sized chunks which in turn would lead to a deeper discussion with PMs and leadership and drive early directional alignment. You get better outcomes and faster decisions if you've run the right learning loops before you get into messaging review cycles.

3. Keep it Simple

The simpler your core message, the more memorable it is. As the saying goes, “I didn’t have time to write a short letter, so I wrote a long one.” Human beings can only retain a certain amount of information, so if you can’t distill your message down to its core, it’ll never land. Use no more than three value pillars. If you’re tempted to squeeze in a fourth pillar for the sake of completeness, you’re not doing your job of simplifying the message.?

At VMware, I trained a global sales force and a large number of channel partners while running several demand gen campaigns in parallel. I sat down with a roomful of new SDRs and made cold calls using my messaging. And I quickly realized that consistency across all channels doesn’t just mean repetition—it means simplicity. Simplicity scales; complexity kills.?

4. Pass the “Friends at a Bar" Test

Be specific. Use everyday words. Write short sentences. Great messaging sounds natural, not like a sales pitch. My favorite part of tech conferences? Hanging out with customers and listening to them talk about their problems. If you’ve never had drinks with any of your customers, find a way to make it happen! Imagine your champions—those already sold on your product—talking to their peers at a bar. What would they say? How would they explain your product? Can you see them using these words?

During our messaging brainstorms we often talk about specific individuals, for example - how would Sam explain this to Brad? If your messaging doesn’t pass the Friends at a Bar test, you’re probably using jargon or language that’s too formal. Keep it conversational, relatable, and avoid anything too corporate.?

5. Answer the “So What?

Don’t just list features; lead with the benefit. People care less about “the what” and more about “what’s in it for me.” For example, instead of “Triple blade shaving system,” lead with “Smoother shave.” and back it up with the specific feature for credibility. This small shift makes the message more relatable.?

If you keep asking “So what?” for every feature your PMs throw at you, you’ll eventually get to the bottom of how you save customers time/money or reduce risk. Go there. Better yet, use real customer examples to quantify the benefits.

One interesting example is Ravello Systems. We built a nested hypervisor in the cloud. This means nothing to anyone. But ask “So what” and you get to the real value prop which was the ability to run VMware workloads on public clouds without any cloud migration. I then simplified my message to “Run VMware on AWS” (it could in fact run on any public cloud but this was a much more memorable tagline).

6. Build Trust. Create Emotional Appeal?

No matter how technical your product, you’re speaking to real people with real problems. Build trust by backing up your claims with technical proof points. Don’t just make big claims—use real data, case studies, and technical proof points. Customers smell BS from a mile away.?Stay away from the fluff.

While most B2B messaging appeals to the rational mind, tapping into your audience's aspirations or fears and telling the right stories will elevate your messaging from good to great.?

At Ravello Systems I focused on dev/test, training, mock security drills and other such workloads that needed burstable capacity but stayed away from lift and shift for production workloads because I knew there was a performance overhead and being transparent about it built immense trust and drove rapid adoption in the customer accounts and use cases where it actually made sense.

At Rockset, one of the most popular content pieces was the Design & Architecture Whitepaper I authored in my very first month there. It got a lot of mileage over the course of 7 years because it explained in great technical detail how things worked under the hood and really appealed to the technical architects and CTOs we targeted. Many of them would tell us "this is exactly what we aspired to build for our backend".

7. Apply the MAYA Principle

I first learned about MAYA (Most Advanced Yet Acceptable) in the context of product design. It is about anchoring on the familiar so you can carry customers with you into the future. This concept holds true for messaging as well. Remember when cars were called “horseless carriages”? And notice how they used the word “horsepower” to measure the power of an engine? That is a great example of new category creation grounded in the MAYA principle.?The goal is to get your point across without a whole lot of explanation.

At Rockset, we considered options like "Real-time Indexing Service" before settling on "Real-time Analytics Database". One was technically super accurate but required a whole lot of explanation. The other used familiar words like analytics and database to indicate where we sat in the stack and what we did. And our initial value pillars were speed (real-time speed), scale (cloud scale) and simplicity (simply use SQL). It resonated really well because our customers real alternatives were single node Postgres which didn't scale or Elasticsearch which was too complex. This is the MAYA principle in action.