GrowthX Academy Blog

By GrowthX Academy mentor Saket Kumar

Messaging is the one aspect of Sales Development Strategy that I think many people struggle with.

It is difficult. I’ve deleted, revised, erased pages of my thoughts on this topic over and over again (one of the many reason it’s so late). I had originally posted this in multiple “chapters” and released them Netflix-style – and then I realized I was wrong and that I hated it so I consolidated into another “Long Form” post. This will take 12-15 minutes read.

Preface – Understanding and Awareness

When I was a kid, one of the most fascinating aspects of life was how people would interact with one another. Early on, I recognized that there are patterns – and you can control and influence the environment and other things to lead and guide people to follow certain patterns and, consequently, a desired result. Sales is an Art – it should be fluid.

Sales can be a Science – there should be a repeatable process and one action should lead to the next.

To do this, it is important to understand as much as possible about the space that you’re in. The more I’ve talked to Sales Leaders, the more I hear that many of the problems stem from the lack of understanding. Whether it be employees not understanding how their product works or could work, not understanding the actual value of their product, not understanding their prospects completely, not understanding their sales strategy, not understanding why things work and why things don’t work. Simply put: Understanding and Awareness helps put together an effective messaging strategy. The All-Star Sales Strategists that I’ve had the privilege of meeting all share this trait: they’re incredibly quick to understand and are hyper aware. You can almost see them connecting the dots in their heads when they’re strategizing and thinking – it’s one of the coolest things to witness.

Some of the key items that I think are important to first understand are: your goals, your target market environment, the ideal target prospect and their goals, why people should want to talk to you and why people wouldn’t want to talk to you and your company, as well as other variables that are specific to your industry and company and most importantly why these things are the way they are without any bias – try to see and understand these things objectively from as many angles and point of views as possible.

Most people will struggle on their messaging because what they believe to be true and what is the actual truth, are different.

This is difficult for many people because they fall victim to the Ikea EffectMastering understanding and awareness gives these Sales Leaders an almost god-like overview of their sales teams. The farther their scope of understanding and awareness goes, the more successful they are.

Without a proper foundation of understanding and awareness, it’ll be difficult to create messaging that resonates and results in positive interactions and meaningful conversations with your potential prospects.

Chapter 1 – Subject Lines

Effective messaging starts with the Subject Line.

In a recent Yesware Study, which analyzed over 100 million emails, they found that the best subject line is….(drum roll please)

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…it’s NOTHING. No, seriously the best subject line is to leave it blank. Yesware attributes this to the curiosity of the receiver to open/respond to this. The study also goes on to mention the usage of “Re:” and “Fwd:” in email subject lines. “Don’t use “Re:” if your email isn’t part of a thread or “Fwd:” if you aren’t truly forwarding an email. Subject line trickery might get you the open, but it will lose you the reply.” I don’t recommend anyone to leave subject lines blank or to use “Re:” or “Fwd:” because they simply don’t work towards the desired goal and it’s disingenuous.

Subject Lines are like half-second trailers to your emails – make them captivating, be direct, leave them wanting more.

Make them like the Suicide Squad Trailer – but unlike the Suicide Squad Trailer, make sure you’re actually mov–errrr body of the email is actually good.

How do you do that, Saket? It’s pretty hard – probably more difficult than the actual body of the email. Crafting a subject lines depends on many factors. The two factors that I think have the most weight on open rates (all things equal) are the Persona and the Size of the company that you’re targeting.

  • Larger companies have more people vying for their attention, thus higher quality and strategy is required than when you’re reaching out to them. These prospects receive tens of hundreds of calls and emails a week – the sheer numbers suggests that you’ll fall through the cracks. Large Enterprises are targeted more than Mid-Market, SMB, and StartUps because of the size of the potential contract value.
  • The Persona is a more difficult understand and explain. People/Industries/Careers are intrinsically different. Sales, IT, Engineering, HR, etc have different feelings towards sales emails, and if you understand how they feel about them you can put yourself in their shoes and craft an email that would be more effective for that personality. I usually start with this assumption: Sales and HR folks are stereotyped as being more extroverted than IT and Engineering folks. Directors, VPs, and C-Suite level people have busy lives and many people vying for their attention versus low level employees who may have more time on their hands. Once you really understand the environment – amazing things can start happening.

When crafting a new subject line, I start by reading articles. Articles are great way to expand your knowledge of your own industry, plus you get to absorb (steal) verbiage from people who write excellent content all the time.

I will literally find a snippet from the article that caught my eye as something powerful/unique and use it as my subject line. As you research, you’ll start finding that some of your target prospects are actually writing, blogging, tweeting, etc online. Take a line from one of their posts and send it back to them as a subject line, and see what happens.

So some of you might be thinking, “Saket, this sounds great, but I’m not going to spend this much time on the subject line!” To this I say: Yeah, this is a lot more time consuming, but anything that’s hand crafted and has this level of customization takes time.

“But Saket, Toyota’s are great cars and I want the Toyota of Subject Lines – the Mass-Market Subject Line!” To that I say: Toyota has over 20 different models and you should be A/B/C/D/E/F testing multiple subject lines to find the ones that work best if you want to take this approach.

Yesware’s study is a solid starting point for anyone struggling with open rates on your emails – however I do warn that subject lines will need to be refreshed periodically because the will get stale as more and more people use them. There is no right way to do subject lines.

So Saket, how do I know my subject lines are successful? Once again, this is subjective and it depends on what level of success you’re looking for. For me, I’m content with a +70% open rate on a inbound prospect with a direct lead source and ~50% open rate on a cold outbound potential prospect. These numbers depend many different factors from your product, market, prospects profile, industry triggers, the level of effort you’ve put into your subject line etc. To do this you’ll need to adjust, modify, and control the variables over time as you A/B test.

…and yes, I know that the only thing that really matters is the positive response rate 😛

Chapter 2 – Personalization

Personalization is one of the best ways to connect with a person.

Think of how boring and mundane talking about the weather is. It’s just small talk that does little to nothing to move a conversation forward – unless of course it’s a natural disaster, that’s much different but probably not the best thing to start a conversation with. Conversations tend go much better when you show interest in the other person.

The initial email has significantly better reception if the recipient can tell that you spent some time and effort to research and understand them on more personal level than just a canned message that you sent to their entire team (this will work even less effectively after your company reaches level of market saturation and maturation).

One of the best messages I ever received was by a recruiter. This recruiter did such an amazing job of doing research on me: New Jersey, Rutgers (my alma mater), and the Grease Trucks (try the Fat Darrell if you’re ever in NJ) that I just felt compelled to respond to her. Her level of detail made me smile and it compelled me to respond in an reciprocative manner. I politely declined, but I admired her level effort – and you know what they say: “The Sale Doesn’t Start Until They Say “No.”

This type of personalization, while highly effective, doesn’t follow any particular formula. To make personalization happen at higher frequency there needs to be a structure to follow. One of the more popular and effective messaging structure that is widely known is the BASHO/Why You, Why You Now technique. This method is really great for getting the prospects attention and letting them know that you “know” and understand them. It’s short, provides value and intrigue and goes for the close at the end. The BASHO/Why You, Why You Now techniques have a very high response rate with 40-50+% response rates being common. What is really important for the success of this technique is the background research that goes into this type of email.

Since there is a high level research individualization that is required on the events, triggers, persona, etc this take significant amount a time and might not be practical with the current pressures and demands of high velocity Sales and Sales Development.

Chapter 3 – The Illusion of Personalization

Since genuine personalization takes an inordinate amount of time there needs to be better ways. One of the most effective ways is by using technology and what I like to call “specific-generalizations” in conjunction with Custom Fields. If you don’t know what Custom Fields are – reach out to the great guys and gals at for more information.

To create this “Illusion of Personalization” you need to have pre-determined sets of information, great data and Modular/Malleable skeletal message that can be applied for large subsets of potential prospects. To get this information you can start by employing data sources like Datanyze*, DiscoverOrg*, DataFox, and RainKing (* Datanyze and DiscoverOrg have integrations with Outreach and makes messaging so much easier). Once you have established a proper foundation you can tailor your messaging based these sets of information, data sources, and “specific-generalizations”.

We’ve all seen the dynamic fields like {{first_name}}, {{title}}, {{company}}, {{industry}} level of personalization – and that’s a great first step, however, on most sales development teams but there’s another level that we can reach right now. Here’s what’s possible: Using the information from Datanyze, DiscoverOrg, etc you can enrich your prospects profile with the tech stack they’re currently using. With most companies having some sort to of integration with another technology we can do 2 things.

  1. You can first segment your outreach via messaging and technology stack. For example if your company has integrations/partnerships with Salesforce, Zendesk, and Office365 – you can search for the companies that are currently leveraging those tools with one of the tools above and then have your messaging actually mention that you know that they’re using those tool in high frequency model which will have the illusion of personalization.
  2. Use “specific generalizations” in conjunction with Custom Fields in Outreach to further perpetuate the illusion of personalization. Specific Generalizations could be a popular use cases that would be relevant to your prospect. For example if your prospect uses Salesforce and your company has that integration with Salesforce you can do something like along the lines of this: “…Companies like {{CustomField}}…”, with the {{CustomField}} being a reference to the gist of a case study or customer reference. This is not just limited to facts and case studies. You can manipulate the Custom Fields in Outreach to be anything – and go full on “Mad Scientist” mode. The only thing you’re limited by is your own creativity and vision.

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*If you’re into “Account Based Whatever They’re Calling it Now” – you can leverage Outreach’s ability to A/B to test to further create the illusion of hyper personalization to an organization. This is only assuming that you’ve mastered your messaging and you’re not still figuring out what resonates. The potential prospects you’ll be reaching out to will most likely be working in close physical proximity to one another and probably even talk to one another throughout the days (gasp – I know right!). This level of personalization will create the illusion that you’ve taken the time to customize each individual message to each member on their team.

The beauty of this method is that it allows the same sequence to be used for multiple Accounts/Companies that share similarities without having sent the same message to literally every potential prospect in that company. This will create efficiencies as you scale your outreach and processes over time.

Some of the Sales Leaders that I admire the most, employ a version of this method to a high degree effectiveness amongst their teams. What’s great about this method is that it allows newer and developing members of your Sales and Sales Development team to get up to speed with more tenured members. This is more advanced and it’s rarer to see because it does require a lot more effort and ground work to create a proper foundation for a messaging strategy to be built on. However, the great leaders know that you can’t build a great team on a weak foundation – you must have a solid foundation if you’re going to build a strong team for the future.

Chapter 4 – 20/60/10/10 and The Duality of Messaging


That’s a lot of random numbers, I know, but I’m sure most people have noticed that when added up, it equals 100. Almost everyone has a different breakdown on how they like their initial email to be structured and constructed to a potential prospect. A common structure that many people focus on is a 20/80 structure with the first 20% of the email being a personalized verbiage to potential prospect and the later 80% being the “value proposition” – this is awesome because it shows understanding of the value of personalization – but like everything else, I’ve observed, this can be taken to the next level by adding additional layers.

Here’s a breakdown of how I like to structure initial messages:

  • 20 – Personalization geared towards the prospect – so they know it’s real. The first 20% of the email is an intro line that is customized to the prospect – this could be something like a promotion, an article, a mutual connection, a sales trigger, etc. I make sure that it’s specific enough that they’ll know that it only applies to them.
  • 60 – Value Proposition, Case Study Example, Customers, etc. – This 60% of the message is the meat of the email. This part will provides the value and why they should care. The wording here is very important and I recommend A/B testing multiple iterations with different verbiage. You can use part of the BASHO method here. (**Adding a Time/Date Anchor within the value proposition will give additional credence to the Illusion of Personalization. This can be reference to a current event. Be creative, your prospects will appreciate that this doesn’t seem like a cookie cutter value prop. For Example: I used Game of Thrones events when the show was still running because I knew it appealed to a large audience as well had a disproportionately high viewership for that specific ICP)
  • 10 – “The Ask” – Ask for whatever you’d like to accomplish. Whether it’s a meeting, to sign up for a webinar, read a position of an article, check your website, buy your product, etc
  • 10 – What to Expect – This what I almost never see in any messaging. This part right will help set proper expectations and tell the rest of the story for your sequence in Outreach and the remainder of the follow up. Something along the lines of ” {{first_name}}, if I don’t hear back from you back by (X Time/Date), would it be ok that I reach back at (Y Time/Date)?”. What this does is get you to a “Yes” or “No” faster for your “Ask” earlier in the message. This is incredibly effective and helps you build the flow and the If/Then statements for the remainder of your sequences/campaigns.

The Duality of Messaging

One of my mentors once told me “Be All Things To All People” – and I must admit, I didn’t really understand it then, but I ponder on this every couple of months – and then it hit me:

To master messaging – your messaging should be all things to all people.

Saket – what does that even mean!?!? It means the messaging should be able to resonate with a wide variety of people and personalities. Pick your words carefully and have it flow in a manner that each sentence and word is reaching out to different type of person and is attempting to accomplish it’s own little goal for the big picture. To do this you need to first understand and be aware of the possibilities for your product and market and then be able to craft a message and structure that you’ve found to be successful for your team. Another important aspect of the “Duality of Messaging” is to sound/type human not a salesperson, or even worse a robot. This probably sounds really meta (or crazy), I think people who’ve created some of the most simple yet complex messages have mastered this.

Chapter 5 – The Path of Follow Up

As we’ve all been told and know, it can take multiple attempts to even connect with a potential prospect let alone get a positive outcome. The overwhelming consensus amongst Sales Leader is that a blended approach of Emails, Social, LinkedIn, Snail Mail and Calls works best – I agree with this. However, it is unlikely that one specific blended approach will work for different companies and target markets. The timings and lengths between the varying touches depends on several factors and it would be short sighted to use the same approach from a company that isn’t similar to your company.

I will often say that sales teams are like humans. All humans have similar skeletal systems, but what differentiates and defines us is the muscular system – hence why sales trainers are able to give insights and advice that are still relevant to different teams.

The foundation (read: skeletal system) of all sales teams should be very similar, but the strategy, execution, and follow up (read: muscular system) of sales teams is as unique as everyone of us. One size does not fit all – be as bespoke as you can.

Speaking of calls and follow up: A few months ago, Blake J. Harber of Lucid Software wrote an amazing article titled “Death of The Cold Call – The Plague Affecting Millions of Sales Organizations.” What I really liked about this article were the plethora of comments. As of this posting there were 1,434 comments. I’ve read every single one and there are definite patterns amongst the sentiments of the people who’ve commented. An analysis of the comments with regards to the commenters current title, company, their target company size, ICP, etc will shed some real insights on the value of calls. Since I know no other way than to do an analysis of LinkedIn comments and commentators – I’ll manually aggregate and compile the data and create corresponding charts, graphs, word clouds, etc. I think this will be interesting – plus with 1,400+ comments we can say that it’s pretty decent sample size, unlike some other surveys I’ve seen. ( I swear, I’ll do this…eventually)

Chapter 6 – Evolve or Perish

When Engineering and Product teams create a truly fantastic product that isn’t just a gimmick – it will practically sell itself. At these early stages, many companies enjoy hyper growth in sales. It seems like every month and quarter they’re breaking another sales record. Things are great, people get promoted, the money is flowing, the company grows rapidly. Then things start slow down, the competition catches up, the sales strategies that were so “effective” in the past no longer work to the same degree. New strategies are adopted, new tools are implemented, sales teams continue to grow – yet the sales pipeline still slows down or, even worse, gets disrupted. The product used to push the sales, and now the product has become “average” so now sales needs to push the product. When sales teams reach this inflection point there are only two options: Evolve or Perish.

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If companies choose to Evolve, there may be changes in sales leadership and/or restructuring on the sales team. This could be coupled with downsizing in an attempting to increase the marginal gains of individual contributors. The great Sales Leaders will also attempt to evolve their messaging strategy to something new. However, this could be difficult if the sales team was not testing and learning over time because the gap between “what is” and “what could/should of been” may have grown too large for the current team to bridge or figure out in a timely manner. If this is the case, it may be a good idea to bring in new blood for a fresh perspective and new ideas if the current ideas and practices are not bearing the desired results. Without proper foresight it may lead more extreme disruptions within the organization – each of which will have their own positive and negative consequences.

If you choose to Perish, then yeah I have nothing…

Chapter 7 – Final Thoughts

You have to Stand Out to be Outstanding.

Envision how every possible scenario will play out in your mind – be strategic.

There is no magic bullet that you can buy…but you can build your own arsenal that is custom tailored.

Work smarter so you can work harder.