How to Create Sales Messaging that Captures your Prospect: The InsideOut Secret

How to Create Sales Messaging that Captures your Prospect: The InsideOut Secret

Keeping Emails Short, Sweet and Succinct.

In a highly saturated and competitive selling environment, writing sales messaging that engages and inspires has never been tougher. 

While the 13 seconds to engage is the generally accepted truth, the real attention span is actually somewhere closer to six seconds. That’s an incredibly short window to catch your prospects’ eye.

There’s no one-size-fits-all approach to writing sales messaging. In order to captivate your prospects, engage your audience and cut through the noise, you need to carefully consider every inch of your cadence, maximizing the unique selling points that best resonate with the pain points of your potential buyers.

Each prospect will have a unique reaction when it comes to engaging with your message – but that’s not to say you should cast a wide net into a small pond each time. Your messaging should be targeted to each and every prospect, tapping into their interests and business needs.

In this blog, we’ll discuss how to create sales messaging that stands out from the crowd.


In a highly saturated and competitive selling environment, writing sales messaging that engages and inspires has never been tougher

Key Considerations for Effective Sales Messaging 

There’s really no two ways about it: to create effective sales messaging, you need to approach the creation process strategically. In the live sales environment, there’s a lot of white noise, saturation and false promises offering you the “one trick to instant engagement success”.

Be careful what you buy into, the reality is that there’s no holy grail for the perfect sales messaging. It’s a rigorous process of building a strategy based on what you already know about your prospect’s market; previous experiences, their competitors, and, of course, the historical data at your disposal.

It’s two-sided. There’s pre-messaging and process, and both stages are top of the funnel activities to bring sales engagement and success into your pipeline. In the following section, we’ll break down the important considerations that should inform your messaging and how you should approach building an engagement strategy that continually wins.

Pre-Messaging Stage

Finding the data to inform your messaging, assets and cadence, driving engagement with proven processes and insight from past experiences.

Strategic Stage

The thinking process for establishing engaging messaging, considering the factors and pain points specific to your buyer and their industries.

Pre-Planning Stage 

The secret to building sales messaging that’s inspiring, engaging and a cut above the rest is all in the pre-planning stage. Before you begin to write a messaging strategy or cadence, you’ll need the data to back up your decisions – and this starts with understanding your Ideal Customer Profile (ICP) and Buyer Personas.

Ideal Customer Profile: Without a fully-fledged understanding of your ideal buyer you’ll never be able to tailor your messaging to target them specifically, or connect with them on a human level.

Buyer Persona: You’ll also want to think about your buyer persona. What a Vice-President cares about and what a Director cares about are totally different. When you form a cadence for both of these decision-makers, you can’t just use the same language or tonality – you need to have two different sales messages; one for your bottom-up approach and one for your top-down.

Look at Historical Performance: If you know that a message, tonality or touchpoint has been effective in the industry previously, maybe for the same persona, that’ll give you a good foundation to build on. Not to mention, it’ll also mean you can identify where your industry-specific messaging misfired previously and save yourself from repeating the same mistakes over.

Sales Motion





The Strategic Stage 

So you’ve collected your ICP, established your Buyer Persona, dug up your assets, and uncovered previous intelligence about what and what has not worked. You’re now ready to go through the thinking process behind building engaging messaging. But, what should go into this?

1. Sales Motion

The first step in forming a messaging strategy is understanding the sales motion. Whether it’s outbound, inbound or upsell, cross-sell, event follow-up or nurture, will change your entire outlook on the rest of the attributes in your strategy.

If you’re dealing with an entirely new Buyer Persona or net new prospect from an industry you haven’t sold in before, you’ll require a more rigorous sift through your historical data to inform the touchpoints at every stage in your cadence. It won’t be as straightforward as applying your data to an existing customer. You’ll instead need to look at your upsell strategies for existing clients and anticipate why they resonated.

2. Segment

At InsideOut, we suggest making segments exclusive – AKA, don’t group small and medium business messaging with enterprise-level messaging.

It’s common sense that these business sizes require unique messaging, totally tailored to suit their specific pain points. Don’t be the salesperson who tries the generic hard-sell to every business with the same message. It won’t work. The way you speak to an enterprise-level company prospect should be completely different to small or medium business prospects.

3. Industry

Say there’s three different industries that your product or service could potentially resonate with, with ample opportunities for increased sales engagement and profitability available. If you’re already pertinent in that market space, even a one percent increase is a big jump because of your influence.

That’s not to say your messaging can be a rinse and repeat across all the industries you are targeting. If your offering has the same benefit across healthcare, SaaS or finance you’re in luck, but the reality is that this isn’t always the case. If it so happens that the benefits are different, you’ll need to create messaging specific to each industry as well. The value may be the same, but the industry you sell to can be one, many or agnostic, no matter the segment.

4. Location

When writing sales messaging of any kind, you need to be mindful of location. Dialect isn’t the only language barrier between North America and EMEA; certain types of sales messaging just will not resonate in the USA as it would across Europe.

Each nation communicates uniquely; there’s no one-size-fits-all across the globe. You simply cannot expect a successful tonality to work in Germany because it’s worked in the USA, no matter if the prospects are active in the same industry. Overseas decision makers have grown to understand what to look out for and you’ll be blacklisted immediately.

5. Asset

Writing your sales messaging is only one side of the coin, you’ll also need to consider the best ways to bring it to life: the content. Guides, whitepapers, case studies, videos; these all play a role in solidifying what you’re trying to say, and where you’re trying to say it. They need to be personalized, targeted and well-thought through.

Instead of just selecting assets on a whim, take the time to understand all the content you have at your disposal, not just a few you think will work. Look at everything that’s been done before and everything you haven’t used yet. Sure, your four-page PDF product guide might look great, but there’s no guarantee it’ll work for every prospect.

Know Your Audience 

The key to effective message writing is to know your audience. That doesn’t change whether it’s inbound, outbound, blended, B2B, B2C, cross-sell or upsell. You can carry out in-depth research into all of the factors above, but when it comes to putting pen to paper (or fingers to keyboard), you need to put yourself in the recipient’s mindset, on a personal level as much as a business one.

It seems obvious, but you’d be surprised how often it’s glossed over. Your ICP and Buyer Personas are a rough guide, but your messaging should always be tailored to each recipient in a way they want to be spoken to.

Remember, top sales leaders all have the same bag of tricks, it’s how these tricks are leveraged to connect with decision-makers, make their ears perk up, and convince them to read further that makes the difference.


Share Insights Across your Team 

No two messaging styles will ever be the same – and from a sales perspective, that’s a good thing. Everybody in your team is going to put their own personal flair into the messaging they write, based on personal experiences and interpretation.

To build messaging that’s diverse, unique and engaging, you’ll want to share insight across your sales team, adding a variety of internal perspectives from different ages, cultures and schools of thought before it’s sent to the recipient. Not only will this help to remove any grammatical or formatting errors, but different perspectives help to minimize the fluff and help keep your branding unified.

Keep it Short & Sweet 

Content stuffing is never a good idea, no matter the context. A one trick win to writing engaging messaging is to find the sweet spot between keeping it short and informative. B2B decision-makers are generally time-poor, so the key is to keep your messaging as succinct as possible.

Nobody wants to read 14 paragraphs about the latest manure spread. They just want to know that it’s going to make their garden grow. You need to get all of that huge volume of research and context down into three to four sentences, or maybe a quick video. Show the value in your offering and why it solves their pain points, then drip feed the other perks throughout your cadence.

Know Your Enemy 

When it comes to prospecting, there’s a lot of fish in a small pond. Sometimes, you just don’t get to your target first, which isn’t the end of the world – you just need to be prepared to blow your competition out of the water.

Understanding your market and sector means keeping one eye on your competitors and the content they’re putting out there. In doing so, you’ll be able to weaponize your messaging to pounce on areas they’re not talking about, or outshine areas they are.

It may sound adversarial, but it’s less about competitor name-dropping and more showcasing that your product/service is the #1 in the industry – and the right fit for your prospect.


Root Everything in Historical Data, Not Gut-Feeling

Don’t Make These Mistakes! 

Thinking you’re Owed a Conversation: 

The sales world has said it a million times over; your prospect does not care about you. You can spend hours slaving away building the perfect cadence for that decision-maker, solving all of their problems, and they still have no obligation to get back to you. Your messaging should always focus on giving the prospect a REASON to take an interest, it’s not a God-given right. If they aren’t engaging, go back to the drawing board.

Being Inauthentic: 

Decision-makers will see right through insincerity. You cannot make sweeping statements about your offering without the stats and credibility to back it up. Your prospects want to see, not hear. The proof is in your anecdotal experiences; case studies and use-case examples in their industry or similar. These give you a competitive advantage that matters to the buyer, rather than just ‘fluff’ that can be disproved on peer-to-peer review sites.

Know your Product & Be Realistic: 

If you don’t have enthusiasm for your product, how can you expect your buyers to? By understanding every inch of what you’re selling, you’ll be able to compound that into your messaging and make it more valuable. But equally, you’ve got to be realistic about your shortcomings, so that when you write content, it is gauging to that context.

Not Continually Improving: 

Testing messaging takes time. One of the biggest mistakes sales teams make is just not being patient enough with their content and being too quick to change. Give yourself enough time to collate vivid, insightful data and then look to adapt and build off the results. This will give your team a cleaner insight into what works, what doesn’t, and where messaging needs to be refined. Don’t settle for mediocrity either; just because it works once doesn’t mean it’s fool-proof. Test, execute, analyze, update, and then repeat.

Sercan Topcu

As a Forbes Under 30 entrepreneur/consultant, Sercan had the fortune of practicing innovative business models and behavioral operations management for productivity in business development with Google Exchange, Hult Prize IXL Center, MassChallenge, MIT Media Lab, and InsideOut PlayOps. Being a Turkish-American who was lucky enough to live in 4 countries and travel to 27 across Europe, North Africa, and the United States.