Writing Better Cold Emails – Boring Startup Stuff

Writing Better Cold Emails

In today's era of drip campaigns and automated sales message, a well-crafted cold email stands head and shoulders above its competition. The only way to write a great cold email is to be authentic and maybe even a little bit weird. In his recent book, Authentic Selling: How To Use The Principles of Sales in Everyday Life, Jeff Kirchick lays the framework for the perfect cold email. For those of us who haven’t spent the past fifteen years in a sales role, the thought of sending cold emails can be scary. Hopefully the except from Authentic Selling will ease some of those nerves.



Authentic & Eccentric Cold Outreach

 

People are weird. All of us are eccentric in one way or another.  

The first thing I tell inside salespeople when I hire them is that I want them to embrace themselves and everything that makes them authentically weird. The weirder they are, the better. And whether or not you like my theory on weirdness, it is absolutely true today that most buyers are inundated with emails, many of which come from salespeople, vying for their attention. What this means is that you need to stand out from the pack. Hence, the weirder you are, the better. Even though Waldo was dressed in strange red and white attire, he was always hard to spot in those “Where’s Waldo?” books because he wasn’t weird enough to really stand out from the pack. And Waldo looked like a pretty weird guy. You need to be weirder than Waldo.

I compartmentalize a good sales email into three parts: The Excuse, The Value Proposition, and The Ask.  

What does this mean in the real world? It means that when I write a subject line for my e-mail, the goal is to get the person to open the e-mail. It is not to get that person to buy my product. It is simply to get them to open the message.  

Here are some better examples of subject lines that are hard to ignore: 

“Hello from a fellow alumnus of X University”

“Hello from a fan of [buyer’s product company name]”

“Fellow Boston Bruins fan looking to connect”

Or, perhaps for a Star Wars fan, “Read or read not, there is no try”

You get the picture. You are using something appealing to your target to establish some mutual synergy. And from there, the goal remains the same. The goal of the first sentence is to get the reader to the second sentence. The goal of the second sentence is to get the reader to the third sentence. The goal of each and every word is to get the reader to the next word. And eventually, as you will soon see, the ultimate goal at the end is to have mutual agreement to meet together. But it is only the sum of the parts – the e-mail in its entirety – which should convince the reader that this is a worthy outcome.

None of this can be accomplished if you are writing an essay to the client. Most people feel out whether or not they have the time to read an email by staring at its sheer size once they open it. If the email is too long, it is likely to get deleted, even if the email itself is some of the finest prose ever known to mankind. This is really no different than how you would approach the proverbial stranger at the bar. If you went up to them and told them your life story, they are likely to be a little creeped out. But, if you led off with something short and sweet about a commonality, it leaves the door open for curiosity that can spark a conversation.

Without further ado, let’s start to dive into the structure of sound cold outreach.

 

Part 1: The Excuse

I call the first part of cold outreach “the excuse” because you are always interrupting someone’s day, and when you interrupt someone’s day, you better have a good excuse. You would never walk up to someone, for example, who is clearly on a phone call, and ask them for directions. If you did, you would at least preface your statement with a good excuse: “Hey, I know you look really busy but this is kind of an emergency so I hope you don’t mind me interrupting you to ask a quick question?” Anything short of that and the person who you are calling upon for help is likely to leave with a bad taste in their mouth over your poor manners, and this makes them all the more likely to decline helping you or to provide you with bad directions. No one wins in that situation.

The excuse for reaching out to someone should always be something personal. Most sales training programs miss this, encouraging the sales rep to open up with some sort of before and after scenario. This could be something about how bad life is today in the absence of the product that is being sold, and what life looks like after, followed by examples of satisfied customers and some statistics to substantiate the point. While none of this is objectively wrong to do, per se, it is also what pretty much everyone else is doing. And if you are fighting for someone’s attention and every single vendor is promising them a better outcome, ultimately it all just starts to sound like white noise.

Here are some examples of successful outreach I have performed.

I found someone who, like me, was an English major in college. She happened to go to The University of North Carolina. Anyone who goes to UNC hates Duke University as they are bitter in-state sports rivals. As a fellow English major myself, I penned an email to this prospect with the subject line “Hello from a fellow English major and Duke hater.” I opened the email by lamenting how everyone told me I would never get a job out of college with my useless English degree and how it was serendipitous for us to find ourselves linking up in the world, both gainfully employed, with me trying to sell her my product. I went on to talk about how we must also have a mutual disdain for Duke. Let’s face it, Duke resembles the New England Patriots in many ways, in that everyone who is not a fan of either team generally has a lot of ill-will toward their fanbases. And this is coming from a diehard Patriots fan. It’s just reality.

The prospect I was writing to wrote back to me saying that the email was clever and that she was interested in connecting with me. Meanwhile, I had only spent one or two sentences in the email getting to the meat and potatoes of what we were even selling – and even then, I left it all in high-level terminology. The point being, it did not really matter exactly “what” it was that I was selling – it was the “why” that is always more compelling. And in this case, the “why” was this commonality we had developed which might lead to some building of trust. From a point of trust, no matter what you are buying, you can at least assume that the seller is going to do everything they can to make sure you are successful. Here is the actual email:

 

Hey [Prospect],

Couple things...

1. Real happy to see a fellow English major thriving in the workforce! They always told me my degree wouldn't be worth much unless I became a teacher, turns out I am saving lives one at a time by selling fraud prevention and call authentication technology.

2. Duke stinks so it's great you did all of this at UNC.

In all seriousness, you look like the person who would vet technology for authenticating inbound callers. I know you guys do some stuff with [our competitor], but we would love to have an opportunity to show how we could augment those efforts. Let me know if you would be open to connecting sometime.

Cheers,

Jeff

 

There is something important I want to call out about this. Nowhere in this email did I compromise my authenticity. I really was an English major in college, I really do enjoy meeting people who shared my major, I genuinely do enjoy joking about us both being gainfully employed, and I also authentically hate Duke (N.B. – apologies to any Duke alumni/alumnae reading this). So nowhere did I sell my soul by writing this message. And this is the thing that is so hard for people to realize in today’s politically-charged climate: you have so much more in common with most people than you would think. If you could only spend a little bit of time peeling the onion, chances are that you would have so much to talk about and agree on if you could get over the obvious differences you see at surface level. It is just a matter of finding out what those commonalities are so you can exploit them and turn them into a positive for both sides. Remember when we talked about empathy a couple chapters ago? You’re going to need that to be able to get far enough with people to realize what values you share. It is those who lack empathy and write other people off entirely that do not even give themselves (and others) an opportunity to see what values they share. 

Another example of a good excuse to reach out to someone is based on content that they have written. I once uncovered the personal blog of a prospect of mine called “The Traveling Parent.” The blog was basically about how this man balanced his work life with his home life. As you can guess by the title of the blog, he traveled a lot for work and rarely saw his children. He had to get creative about using technology to stay in touch with them, and when he was at home, he needed to set certain boundaries in order to maximize his time with his children. I was actually personally touched while reading his blog. And even though I am not a parent, I do travel quite a bit for work and I could really empathize with his struggle through my own personal experiences of feeling homesick whenever I would hit the road for a new destination. I wrote him a message saying as much after dozens of failed attempts to connect with him previously, and surely enough, he wrote back to me with an interest in meeting. In this scenario, it was by making myself vulnerable that I showed him my humanity, and he responded in kind.

Content that people write is ripe for good, genuine connections. A personal blog is one thing, but oftentimes people are also writing professionally about subject matter that is relevant to their work, or even for volunteer work that they do in their personal time. For example, I am a volunteer in the Big Brother Big Sister program. People who participate in that program have a dedication to mentorship and serving underrepresented communities. That alone is a great reason for connecting with someone who participates in the same program or has undertaken any other sort of commitment to mentorship in their lives. Or if that individual has contributed thought leadership for a publication like the Harvard Business Review, you might find some meaning in what they had to say and explain to them why it resonated with you and why it makes you hopeful that a conversation could be mutually beneficial. 

Now, it is one thing to have a good excuse to reach out to someone and to share that with them. But once you have made your excuse, you need to have a compelling reason why you merit their attention. And that is where the Value Proposition comes in.

 

#2: The Value Proposition

A value proposition is exactly what it sounds like – the proposed value that you are bringing to a prospect. The best value proposition should really be short and sweet. You often hear the term “elevator pitch” and you see competitions where people have to give elevator pitches in a very short amount of time. This is intentional. If you are unable to explain what value you can add succinctly, it probably means that the value you add is nebulous or confusing, because otherwise it would be easy to explain. Moreover, people have short attention spans, so you really need to cut to the chase when explaining what value you can offer 

First though, let’s make sure we do not make the most common mistake that I have had to correct within my own ranks. A huge mistake that I often see is people getting so wrapped up in their “excuse” to reach out, that they forget about it for the rest of the email. They might say something like this:

 

Dear So and So,

Your recent article on the bureaucracy of procurement processes really caught my attention because I have long held the same beliefs. Thank you for being a voice of reason. I particularly liked the part where you called out how the best vendors are often not selected as a result of this bureaucracy.

I am reaching out to you because you are the Head of Procurement at XZY Company. We sell a product that eases the burden of onboarding new vendors.

Let me know if you are open to catching up next week to brainstorm about this.

Sincerely,

Learning Sales Rep 

 

If you cannot spot what is wrong with this message, that is because it is quite subtle: there is no connection between the first and second paragraphs. The writer goes from discussing an article to immediately explaining why they are reaching out to the person and what they are trying to sell to them. It almost makes the first paragraph look disingenuous, because the “personal” part of the email is immediately discarded in lieu of a straight up sales pitch. Fortunately, it does not take much to fix this. It would be as simple as using this transitional sentence: “Because you seem very interested in figuring out ways to make the procurement process easier, I thought it would be a good idea for us to connect and brainstorm about our product, which does X, Y, and Z for you.” As long as you are giving a reason why your excuse somehow ties to your value proposition, you are golden. But if you suddenly forget your excuse in the interest of jumping right into your pitch, it will leave the recipient wondering about the relevance of your excuse if not for anything other than to indicate you have some things in common, which might have nothing to do with the conversation the individual is trying to have with you.

With that being said, I do think the transitional sentence I proposed above is highly effective because it also subtly puts the reader in a position where saying “no” might not be in accordance with their stated goals. If someone has gone out of their way to publicly criticize a specific problem and you reach out to them stating that you are reaching out precisely because of their criticism, it puts the reader in a position where they feel compelled to respond. Certainly when I publish this book and then get bombarded by sales emails about authenticity, I would feel like a hypocrite to tell those salespeople to go pound sand. Working this type of language into your value proposition as a quasi-excuse or transition phrase can be a small but highly effective maneuver.

The scope of the value proposition depends largely on what you are selling and what industry you are in. For the last seven years, I have been selling into a very niche industry against just a couple of competitors. Generally speaking, my audience consists of people whose job largely revolves around understanding what vendor solutions are out there. My value proposition can be fairly high-level and straightforward – “we are one of the vendors doing this very niche thing and I do not believe we have had an opportunity to meet before, so let us know if we could connect.”

Unfortunately, for most people it is not so simple. But that does not mean that the solution is much harder. My high-level thesis is that the value proposition should be 1-2 sentences, 3 at most, it should tie the excuse into it in some way, and it should speak mostly in terms of measurable outcomes or “whys.” What are those?

Well, outcomes are fairly obvious. These are the things that happen for the customer when the customer buys your product. Measurable outcomes assign some sort of specificity to the outcome – like saying “we will triple your revenues” versus “we will increase your revenues.” A “why” is actually not an outcome at all – it’s just an explanation for why you and your company care about this problem and why you want to help. Why is the “why” important? For all of the reasons we have already discussed. People get onboard with ideas if they feel commonality with those who share the ideas. If you are selling a customer experience product to a customer experience professional, chances are, that customer experience professional is passionate about customer experience. What better way to establish commonality than to explain why you, too, care about customer experience?

Now that we have established how the Value Proposition works, let’s go back and re-work my email from a moment ago. Here is what it might look like now:

 

Subject: Your article in Procurement Magazine

Dear So and So,

Your recent article on the bureaucracy of procurement processes really caught my attention because I have long held the same beliefs. Thank you for being a voice of reason. I particularly liked the part where you called out how the best vendors are often not selected as a result of this bureaucracy.

Since you are so passionate about innovation in the realm of procurement and making life easier for procurement professionals, I was interested in brainstorming with you over our new solution. We are seeing a 3x increase in efficiency in private betas for procurement professionals and it would be an honor to get your feedback.

Let me know if you are open to catching up next week to look at this.

Sincerely,

Improved Sales Rep

 

 This hits the formula perfectly: subject line that is impossible to ignore, establishing commonality, transitioning that commonality into a compelling value proposition with measurable outcomes, and an easy call to action.

 

 

#3: The Ask 

Let’s be honest – you are interrupting someone’s day because you want something from them. To be fair, you must feel that they stand to benefit from spending time with you, too. You are not going to get that time unless you ask for it.

The ask is relatively simple compared to the other concepts we have covered in this chapter. Take a sentence and ask for whatever it is that you need. Because most conversations I have with customers are really brainstorming sessions, I like to use non-threatening language like “it would be great to brainstorm with you” or even the more ‘sales-y’ but still less threatening “let me know if I could introduce the concept to you.” Regardless, I think one of the most important things you can do when asking for something is letting the person know that you are OK with them saying “no.” It is often taught in sales trainings that you should not introduce objections to customers, and while I think that is often true, I don’t see the harm in showing a customer that you are not going to be pushy. I like to close out many of my messages with something like this:

 

“Let me know if you are open to brainstorming on this idea with me next week. If it’s not your cup of tea, I understand.”

 

When it comes to the examples I have used in dating, I realize that my example above does not necessarily hold water. It can be a turnoff for people to appear to be lacking confidence. For example, you are unlikely to ask someone out on a date with the caveat that you would be understanding if they rejected you. But people that you ask on a date for the first time are oftentimes not people that you know very well. And quite frankly, if you did know them well, you would be likely to add the caveat, “I’d understand if you said no, because we are such good friends.” Really, giving an “out” to someone is the same exact way you would treat a friend. You would not bully them into accepting your idea – you would let them know that your friendship will still be intact even if they disagree with you. The same is true here: ask for what you want but show the person that there is much more to life than whether or not they take you up on your offer.

One thing I really try to avoid in my cold outreach and really in all of my selling is looming deadlines. This is an artificially-imposed deadline on someone meeting a call to action. Generally speaking, looming deadlines hinge around pricing, e.g., “If you buy our product in the month of September, it will be half off.” This is gimmicky because it is not authentic. It is gimmicky because it is what car salespeople do to you and honestly half of the promotional emails in your inbox – which we have established can be used as a rule for what not to do – are probably employing the same tactic. When you are having a serious conversation with a close friend or family member and recommending a certain course of action to them, you probably would not tell them they need to take your advice immediately or risk everything. Realistically, you would only do that if there was actually a compelling reason to do so. In traditional sales settings though, the looming deadlines you experience are rarely motivated by real timing hurdles. They are almost always motivated by someone who needs to bring a lot of revenue in the door at a certain time. When your favorite retailer has a sale, it is not because there is something about the given month that makes it more affordable to them to sell you clothes. It is because they know that offering you a looming deadline has an effect on human psychology.

Now, I know what you’re thinking. Something like, “Jeff, you already told us you were an English major in college and that you know nothing about psychology. Why should I listen to you when every marketer in the world does this stuff?” Well, that is because people who market en masse are very different than people who market in unique business-to-business settings. If you work for a business-to-consumer company (think Amazon, or any large retail brand), looming deadlines will probably be effective for you, so go ahead and disregard my advice. However, if you sell large enterprise contracts like I do, the people you are dealing with are much more likely to see through your nonsense and feel that you are trying to rush a process that takes time. I recently moved forward with a vendor who offered me a looming deadline. I did not like that they had a deadline on their pricing, but they told me that they were raising money from investors and trying to bring in as much revenue as possible to help with their valuation. The more revenue they could show to the investors, the less dilution of their stock they would face. I believed them, and I signed up for their product. Surely enough, weeks later, they announced their Series B fundraising round. Here is the moral of the story: if you are going to use pressure tactics to try to bully someone into a sale, at least be genuine. I have been honest with my clients about why I ask for things when I ask for them so that they see that my demands are coming from a place of authenticity and that they are not borne out of just trying to close a deal. If people are made to feel in your outreach that any urgency you have is legitimate, they will act in kind. However, if they are made to feel like you’re just trying to push them, they will also react in kind (i.e., not kindly) to that.

It is probably self-evident how these principles can be applied to everyday situations. My cold outreach method is useful when you are reaching out to anyone for the first time about anything it is that you desire. It could be valuable in reaching out about a potential job opportunity. It could be valuable in reaching out to a college admissions counselor. I suppose it could even be valuable for people who are looking for a better opening line on whatever dating app they use. But whether you are sitting behind a computer or not, the same principles hold true: try to remember the humanity of people around you and appreciate others for their own authenticity. Try to connect with them in a personal way and you will be pleasantly surprised by the results. 

 

Jeff Kirchick is Vice President, Enterprise Sales and an early employee at Next Caller, a Y-Combinator backed technology company that sells authentication and fraud prevention technology to Fortune 500 brands across the United States. He has had unparalleled sales success for over a decade and enjoys the opportunity to help mentor and coach younger sales professionals looking to get their start. He is a big believer in saying what you have to say whether it is going to be popular or not. You can find Jeff on LinkedIn or his website.

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