Writing Great Emails

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Intro

There are more than 1 million words currently published on the internet that will give you advice on how to write a good cold email. And there are probably close to 1 million dollars in courses that you could buy to teach you, many of which would give lots of the same advice you’d find here for free.

Most of those words weren’t written by people who have sent millions of emails and generated more than $1B in pipeline for their clients. These are metrics I share not to brag, but to tell you that I’ve experimented a lot. I’ve bought the courses. I’ve read the advice. I’ve tested just about every kind of email you can imagine. This gives me the confidence to write you a guide about what actually works, why it works, and how you can write your own emails that get positive, revenue-generating replies.

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What we’ll cover in this chapter

The rest of this section will teach you:

1. How to decide who to email.
2. How to write an effective email to that specific person.

What you read below will not be a copy-and-paste template to use in your campaign. That’s not productive: it’s like giving a man a fish instead of teaching him to fish. Instead, the below aims to deeply engrain the theory, the tactics, and the logic into your head so that you can sit down in any situation, write an email to any person, and know that it is going to be good.

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Who should you email?

You already know who your customers are: it would likely be easy for you to write me a list of 10 companies you think would be perfect buyers for your product.

The conventional approach, then, is to create your buyer persona and then go find people who fit that persona at every company and email them. This can be fine. But to determine who you send cold outbound to, I want you to do a quick exercise—regardless of whether you have a clearly defined buyer persona or not. Answer the following question:

Who is currently feeling the pain that our product solves, and how do we know they feel this pain?

If you’re selling cold outbound to startups at the Series A stage, then the people feeling the pain might be the founder and the head of growth (or marketing), and the main ways you’d know they are feeling the pain—outside of just assuming it—is looking to see if they’re 1. Currently hiring sales reps and/or growth people, and 2. Currently running ads. Do an exercise like this for whatever your company does and see what you come up with.

Your answer may be the same as the persona you already had in mind, and if so, that’s great. If your answer is different, though, then think about why. No matter what, you’ll find most success if you email the people, and companies, that are feeling the pain that the product solves.

This is called pain sniffing: it’s a more thoughtful approach to prospecting, because it looks for the people who actually have the problem your product solves as opposed to the people you think your product will be helpful for. We’ll go deeper into how to scrape for these pieces of information at scale in the next section, which covers scaling with AI.

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On whether to email the higher-ups or lower-level employees

Once you know what companies and department(s) you’ll be emailing, you’ll also need to ask the question: who specifically should I target, especially if there are multiple people at the company that are relevant to the pain my product fixes? Here’s our framework at Aurora and Za-zu:

• If the company is less than 50 people, you can and should email the founder.
• If the company is 50-100+, you could email the founder but should also email other decision-makers.
• If you’re not sure who’s the decision-maker, email the person who is higher up.
• Unless the company is very small, you can and should email multiple people at the company.

Use these plus your intuition to guide you as you decide who to email.

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How to get the right email addresses

Once you know who you want to email and what company they work for, getting their email is easy. At my agency, Aurora, we use Clay to enrich all kinds of data you can use when you email prospects (more on that in the next section).

Making sure you’re sending to the correct email addresses is important, because emails to incorrect addresses bounce—and having an abnormally high percentage of emails bounce is a clear red flag to ESPs that you shouldn’t be trusted. If you’re using Clay, you can enrich the emails via Clay and then use one of their integrated tools (like ZeroBounce or Debounce) to verify emails so you know you’re sending to valid addresses.

You don’t have to use any of the tools I just mentioned: there are 100s of email enrichment and verification tools online. Just make sure you are using some and that they are reliable.

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How to write emails that get positive replies

Contrary to popular belief (or what you might read online), a good cold email will not come in the form of a template. All you need for a good cold email is to convince someone that the thing you are selling will make their company money and/or make their personal life better in some way. Doing that can be complicated and will change by person, but in the next few minutes you’ll learn a bunch of useful heuristics.

The trickiest part of writing a good cold email is doing the following:

1. Getting the ideas right (convincing them it’s valuable)
2. Nailing the style, tone, and jargon (sounding natural, not naive)

Below are the heuristics we use and things I’ve learned. For the rest of this section, pick a specific person at a specific company to write an email to. It helps to think of someone in particular and not a vague idea of who you want to email. We’ll automate all of this later.

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Getting the ideas right

To find the ideas that are going to work in a cold email, start by asking how you will be valuable to a company. These ideas generally fall into one of two categories:

1. How do I make their company more money?
2. How do I make this specific person’s life easier and/or better?

Why these two? In the 1000s of campaigns we’ve run at Aurora, there is one common denominator: the best emails frame the product as a profit center. And, in the end, people are also very concerned about their own well-being. If you’re selling a product that will make somebody’s life fundamentally better in some way, they’re more likely to reply.

Coming up with your big claims is the first step. The next is to turn them into convincing arguments. At my agency, Aurora, we did this in a novel way: we used debate-style contentions to make sure our arguments were solid before writing emails.

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Strengthening your ideas with contentions

You can’t win a debate without well-structured arguments. In the world of cold outbound, most people don’t know this and their ideas are poorly structured. Here’s a helpful contention format you can use to strengthen your ideas.

Claim: The perspective you have.
Warrants: Logic explaining why that perspective is valid.
Evidence: Credible data backing up the claim.
Impact: Why the claim matters to your prospect.

Write one contention for each claim you have (and you probably have more than one). If you struggle with one, it may be a sign that the claim itself isn’t very good.

Imagine, for example, you run a cold outbound agency and are emailing founders at early-stage startups. One contention you could write might look like this.

Claim: Cold outbound is one of the highest ROI ways for early-stage companies to grow.
Warrants: It costs very little to send an email. You can send lots. People can convert quickly.
Evidence: I’ve generated millions in the pipeline for early-stage startups with cold outbound.
Impact: You could add substantial new revenue this quarter at a relatively low cost.

Writing contentions like this is more than just a novel way to strengthen your ideas—you’re actually doing a lot of the email-writing work upfront. Once you have coherent and effective arguments, writing a good email is little more than putting them together in a personalized way for the person you’re emailing. Before we put everything together, let’s cover style and tone.

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Nailing the style, tone, and jargon

There are a bunch of overcomplicated ways to think about style and tone. One useful way to think about it is on a basic scale from casual to formal.

This is the only tone scale that really matters, at least when you’re writing cold email.

**Why? **You want your cold emails to blend in; to feel like real emails real people would send. Some industries and people communicate more formally than others. Emailing early-stage startup founders allows you to use more casual language, while emailing Directors of Compliance or Finance at large healthcare companies requires a more formal tone. Your most valuable email calibration will generally be asking: “Does this sound too casual or too formal?”

One surprising insight here is that many people confuse the difference between casual and formal, and I don’t want you to be one of them. To be clear:

Casual tone: Closer to how you’d communicate to a close friend.
Formal tone: Closer to how you’d communicate in a serious job interview.

One common failure mode is thinking you’re writing in one of these tones when you actually are not. Take the following email, for example, which the sender might think is written in a casual tone but in reality is not:

Heya, Matt —

Was browsing around for too-good-to-be-true startups and found Za-zu 👀

I noticed you’ve put out a roll call for rockstar salespeople!

Made me think — think ‘ya could use a hand with cold outbound? My agency does just that. We’ve worked with tons of big companies and could make your revenue skyrocket (really).

Would it be insane to chat this week?

See ‘ya,

-Person Who Writes Bad Emails

Some people have the misconception that an email like the one above is casual. Ask yourself, though: would you ever speak to a friend or close colleague like that? You wouldn’t.

The email above is a formal email disguised as a faux-casual email with a bunch of language that would not be considered professional. Emails like this exist because writing like you’d talk to a friend, when you are in fact not talking to a friend, can be hard.

Here’s what the email above would look like if it actually was casual:

Hey Matt —

Friend of mine told me about Za-zu last week. Congrats on the recent raise.

Random, but noticed you’ve got a few jobs open for SDRs.

Reason I’m reaching out is I run a cold outbound agency. We can send at 17x the volume of a typical SDR, and our emails are usually twice as effective. Have generated $1B in pipeline for companies like Angellist.

Worth a chat this week?

-Person Who Writes Better Emails

See the difference?

To decide what tone you should write in, think about what tone you think your customers use when they’re talking to colleagues, external vendors, and so on. It’s likely that you already have a strong grip on the way that your customers talk—lean into that and write in the same way.

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Making sure you get the jargon down

One frustrating thing that can sink an otherwise-great cold email is not using the right industry lingo. Every industry has a certain way of talking about things, and not conforming to that way will make you look like an outsider—someone who just wants to sell something.

At startups, for example, you might hear terms like:

• “Raise” to talk about fundraising
• “ARR” to talk about annual revenue
• “SDR” to refer to a salesperson
• “Cap table” to refer to the spreadsheet showing ownership stakes in the company
• “Runway” to explain how much longer a company can financially sustain itself
• “a16z” to refer to the venture firm Andreessen-Horowitz

There are hundreds of terms like this for every industry. If you’re going to write emails to people who work in those industries, you should know what the terms are. Finding them out is pretty easy—if you know your market well you should already know them. If not, find out where those people hang out online (Twitter, Reddit, etc.) and pay attention to how they talk.

You should also pay close attention to how a company might refer to themselves. If you are writing to Sequoia Capital, for example, you should probably just refer to them as “Sequoia” in your email. Otherwise it feels like you pasted their company name in from a spreadsheet of data.

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Finally, here’s how to write an email

Now comes the fun part. At this stage, you:

1. Have the right ideas and arguments.
2. Have the right style, tone, and jargon.

Putting them together is surprisingly easy, now that you’ve done the hard part. Just follow the steps below, pay attention to examples, and practice 100s of times to get good.

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Most good cold emails have these components

There is no one universal template that will make you millions of dollars. But, most great cold emails do have the following elements in them, not necessarily in this order:

• Personalization
• Strong claim
• Evidence for that claim
• A clear next step
• Shorter than ~200 words

Include all of these in your email and you are, probably, golden.

The most important piece to clarify here is “Personalization”: lots of people have the idea that this means opening your email with a line like, “Hey, I loved your post on LinkedIn last week!”

And while sometimes personalization might mean a cheesy line about LinkedIn, what’s important is that there is something in your email that makes it feel 1:1. People, more these days than ever, have their mental spam filter on when they get an email from a stranger. If there’s nothing in your email that indicates it’s personal and not a template sent to 1000s of people, you’re probably getting sent straight to trash and possibly marked as spam.

So how do you write? Everything you’ve read so far has prepared you to write—now just start drafting. In the section below, I’ll leave some examples of emails that have performed well for Aurora, so you can get some inspiration for what a good cold email might look like. Remember, though, that your email should be perfect for the person you are emailing, and that examples you see online might not reflect what will work for you.

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Examples of cold emails that have worked well

Hey, [redacted_name]

I have buyers considering companies dedicated to synthetic biology in [redacted_location] doing north of $10M.

Usually when I reach out to owners they are not interested in selling (at least in the short term)

Regardless would you want to hear from the buyers?

If you’re up for it, we could plan a quick chat, and I can help with the introductions.

Cheers,

[redacted_sender_name]

p.s. If my emails aren’t your thing, just let me know. I promise, no hard feelings.

[redacted_name], hello.

Just a quick question — is running [redacted_company_name]‘s profit sharing program a pain?

If so, I’d love to chat about how [redacted_product_name] simplifies profit distributions.

It integreates with your cap table/waterfall, and provides your stakeholders a modern portal to connect their bank account and sign and access documents.

No more handling payments manually. Complicated tax tasks off your plate. A smoother experience for everyone.

Would that be helpful to [redacted]?

Thanks,

[redacted_sender_name]

Hey [redacted_name],

Hope you’re doing well! I heard you’re looking for engineers in Costa Rica. Finding the right people can be tough.

[redacted_company_name] connects companies with super skilled engineers from LatAm, all of them pre-screened by other engineers within our team. In just three days, you’ll be speaking with potential hires. Interested to try us out? (there’s no cost until we help you fill a role). No worries if not.

Best, [redacted_sender_name]

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Creative ways to increase your open rate

So you can write a great email. That’s the hard part, so congrats. But there’s still one small part left to cover: how do you make sure people actually open your emails? This is important, because none of that wonderful copy is worth anything if your recipients are not reading it.

The best way to increase open rate is to make sure your emails hit your recipients’ primary inboxes—we’ve already covered that. On the email level, though, there are two useful things you can do to boost your open rate:

• Write good subject lines: My best rule for writing good subject lines is that they feel like they could be the subject lines of an internal email—this helps them feel natural in the inbox. For example, “Quick question”, or “Idea for better outbound” are two casual, natural-feeling subject lines. Of course, A/B test in your sequencer to see what works.
• Use a profile picture: Including a picture, preferably the face of whoever the email is from, is one way to separate your email from the 1000s of faceless scammers. Getting deliverability right is essential for either of these to have much of an impact. But, if your emails are hitting primary inboxes, good subject lines and profile pictures can go a long way towards getting those emails of yours read.

By the way, are you finding this playbook valuable? Enter your email below and we’ll let you know when we post pieces about cold outbound. We publish thoughtfully (you won’t be getting multiple emails a week) and focus our writing on cold email tactics and insights.