The Cold Outbound Handbook

Table of Contents

Intro
I. Why Cold Outbound Works
II. The Infrastructure
III. Writing Great Emails
IV. Sending Personalized Outbound at Scale
V. Launching Your Campaigns

Intro

There are few growth levers that could allow a single person to grow a startup from $0 to $1M ARR in a matter of months. There are even fewer that could be done with nothing but an internet connection and a laptop—and virtually no budget.

Cold outbound is one such lever.

Within seconds of this very moment, you could send an email to your dream investor. Or a potential customer. Or Patrick Collison. A few minutes from now, that person could reply. And a week from now, you could be on the phone having a conversation that will change the course of your company and your life. It’s almost unbelievable how powerful cold outbound is: in business, you can get almost anything you want with a damn good email. If we can be honest for a moment, though? You’ve already heard this.

You know cold outbound works. Companies have been built on the backs of cold outbound. There are millions of words already published on the internet that claim to teach you how to do it well. There are agencies and tools and services that want to be your golden goose, your silver bullet, the thing that makes cold outbound finally easy.

So let’s agree on one thing: there is no silver bullet. Cold outbound is not easy. It is not easy to generate millions of dollars in pipeline, and to then turn that pipeline into revenue. It is not easy to send emails that strangers answer. It is not easy for one or two smart growth people to drive sales like they were a team of 50 SDRs. It is not easy to email people right when they’re facing the problem you solve, and to write messaging that convinces them you can solve their problem.

It is, however, possible.

This playbook will show you how to run outbound like the smartest growth people in the world. Do it right, and you and your team will be able to build personalized cold outbound campaigns, run them at scale, and make millions. The path to get there won’t be easy. But, by the time you finish reading this, it will be clear.

Why you may consider listening to me

I bootstrapped a cold outbound agency called Aurora: we’re on track to generate $500M in pipeline for our clients in 2024, and we hit $1M in ARR in less than 12 months—all using the tactics you’ll find below. We have sent millions of emails and booked thousands of meetings, for companies in industries from podcasting to customer loyalty to edtech. If we hadn’t figured out how to run effective cold outbound at scale then we would not exist, and I would not be writing this playbook. Now I’m building Za-zu, the cold email sequencer built for personalized outbound at scale.

I started Aurora after spending years raising millions of VC money, trying to build a unicorn. If I were to go that route again, cold outbound is the first thing I’d do to generate a ton of traction and revenue for my business. Because it works.

I. Why cold outbound works so well

The internet sucks on a very regular basis. Spam, noise, content you don’t care about, ragebait, fighting, ads for questionable cryptocurrencies. And while ads work, especially for specific kinds of products, they are an impersonal and expensive way to grow. You couldn’t hand $10k to a smart growth person and expect them to 10X or 100X that money by buying ads on Twitter or Meta.

The inbox, though, is still at least a little bit sacred.

Email is where important conversations happen. It’s where you make sales, where you get hired for jobs, where you have important conversations with people in your company, where you read the news you’re interested in, and so on. Email is still your own little corner of the internet.

This intimacy is what makes cold outbound such a powerful channel. While most advertising involves you renting space somewhere—the digital equivalent of a billboard—cold email is a direct line into the inbox of the person you want to sell to. And when someone sees a cold email that’s interesting, they don’t need to click on an ad, then go to a website, then click on a CTA, then book a demo. All they need to do is reply.

Cold emails don’t work all the time, though. To be specific, cold emails work when 1. They land in your recipient’s inbox, and not in their spam folder, and 2. The recipient thinks that you can do one of the following for them:

• Make money
• Save money
• Save time

If you can convince people that you can do any of these things for them, you can make a lot of money. At my agency Aurora, in just the past year with cold outbound:

• A podcast production company generated $46.5M in pipeline in 14 months.

• A small business marketplace has generated $3.6M of pipeline in 5 weeks of sending—and hired a new salesperson to keep up with the demand.

• A cap table management platform booked 23 meetings (~$230k in pipeline) in 4 weeks.

• A financial underwriting company secured 20 meetings with Fintech buyers in just 20 days.

I say these things not to convince you that I am especially great, or that my agency is great, or that you should work with us. I share these metrics because they are achievable, as long as you can send thoughtful and personal cold outbound campaigns at scale. Behind every metric like the ones above, you won’t find a generic, spammy cold outbound campaign. Instead, you’ll find ideas like:

Later, we’ll cover how to come up with ideas for campaigns that work, write great emails, and get results like the ones above (I’ll show you some of the exact emails we used).

At this point, though, you may be wondering: why isn’t everyone doing this? Why doesn’t every company just pick up an extra few million dollars by running some cold outbound? And the truth is that it’s because cold outbound is very hard. While you can set up an outbound campaign in an hour or two, that outbound campaign probably isn’t going to be good; so many campaigns end up as failures, 1000s of emails sent with hardly anything to show for it. Many of the clients that originally came to Aurora came to us because they’d spent tens of thousands of dollars working on outbound internally, hadn’t seen many results, and were frustrated.

The good news is, the two reasons why cold outbound is hard are both solvable:

1. It's hard to write a good cold email.

2. It's hard to scale good cold emails beyond what you can send manually.

The rest of this playbook will help you write great cold emails, then use AI to send those great cold emails at a scale you’d have to hire an army to reach manually. So you can saturate your entire available customer space rapidly, and get whatever it is you want to get—with email.

II. The Infrastructure

Intro

If the world’s best cold email is sent but it never reaches the recipient’s primary inbox, the email is worthless. Infrastructure is a prerequisite for good outbound: you might be able to succeed with mediocre emails and great infrastructure, but you will never succeed with great emails if your infrastructure doesn’t work.

The tragic part is that most outbound campaigns fail right here. Most people don’t want to put in the work to figure it out. And their campaigns fail. That in mind, this chapter will prepare you to run cold outbound campaigns. The next chapters will teach you how to write and send emails.

I have spent 1000s of hours looking into this stuff. Some of the below may be easily findable online, yet not very well organized. And other parts of this information are insights I only learned after months of sending millions of emails for our clients. The below is a practical step-by-step to setting up the infrastructure so that you can focus on writing, and sending, winning emails.

What we’ll cover in this chapter

The whole point of this chapter is making sure your emails hit the right inboxes. This work often seems scary, but it shouldn’t. Everything we’ll cover here is in one of the following categories:

1. Buying and setting up adjacent domains.

2. Optimizing your domains for deliverability.

3. Setting up email inboxes on your domains.

4. Optimizing your inboxes for deliverability.

What if you skipped all of the infrastructure work?

It’s tempting. If you decide to forego everything on this page and get straight to writing and sending emails, then your sending infrastructure will look something like this: one email account, from your main domain, sending to all of the people you want to send to. This could scale linearly with however many SDRs or marketing people you have on your team.

But unless you only want to send a few emails per day (and even then, this is not optimal), this is a horrible idea that will—in a matter of days—likely get your emails sent to spam and perhaps even penalize your company’s entire domain. Sending hundreds of cold outbound emails from individual inboxes, or even individual domains, is a clear red flag.

And yet this one account per person tactic is what most companies, and the SDRs that work for them, are doing. Millions of SDRs worldwide wake up, write a few dozen emails, and clock out for the evening. It works, but it’s not efficient and it’s not what this playbook is going to help you do. When you are done reading this, you will know how a single person can send with the volume and personalization of an army. Without setting up the infrastructure, one person can send just 20 or 30 great emails a day—we want to send 2,000.

So why doesn’t it work to run your cold outbound like the diagram above?

1. Email Service Providers (ESPs), like Gmail, want to see human-like volume being sent from email accounts. And most humans do not send hundreds or thousands of emails per day.

2. If you get flagged for spam, your entire domain could get penalized—which means you shouldn’t ever be sending cold outbound from your company’s actual domain. You shouldn’t be sending outbound from just one domain in general.

3. Your emails are at risk of getting sent to spam if you haven’t set up your SPF, DMARC, and DKIM records for the domains you’re sending from.

Deliverability is also an issue at the email level—you can’t have spammy emails—but we’ll cover that in the last chapter of this playbook, which is all about how to scale.

Buying domains and setting them up for deliverability

In order to send at any reasonable scale, you need to buy what I call adjacent domains: domains that are similar to your company's. In the case of my company, Aurora, our actual domain is helloaurora.com—but adjacent domains might be:

auroraemails.com
yesaurora.com
withaurora.com
getaurora.com

And so on.

Why not just any domain? Because all the recipients of your emails will see your domain name in your sender email address, and there will be a lot of eyebrow-raising if you picked something that seems suspicious (e.g. buying floridapanthershockey.com if your business is gardeningtools.com).

Once you buy the domains, you should 301 redirect them to your main domain. For example, if I bought withaurora.com, I’d redirect it to helloaurora.com, our actual domain. You do this so that if someone who sees your email decides to copy and paste your domain into their browser (this is common), they hit your real website. You’d be surprised by how few people are surprised when domains redirect this way, or even notice it. It’s less of a problem than you probably think.

How many adjacent domains should you buy?

The number of adjacent domains you should buy depends on how much email volume you want to send. At Aurora, we set up 3 inboxes per domain and send 20 cold emails per inbox per day, which is about what a normal human sales rep would send. If you already know how much outbound you want to send, you can use a simple formula:

The “1.1” exists in the formula to make sure you buy some reserve domains; in other words, domains that you don’t strictly need and will not use immediately. These domains exist for those situations when some of the domains you are actively using in a campaign start to experience deliverability problems—which happens from time to time. We’ll cover this in more detail in the final section of this playbook about scaling your campaigns.

If you want to send 60 or fewer emails per day, you may just need one domain to get started. If you want to send 6,000, you should buy 60 domains. This is not a hard rule, but it’s a good heuristic you can use to get started. Your experience while sending may vary, and you might change your mind down the road. But it has worked for us at Aurora.

There is a separate question here: How much daily volume will I send? We'll cover that later, when we talk about who to email and how many emails to send them. If you have a small TAM (imagine there are only 5,000 people who could be your customers), then you likely won't need many domains. But if there are tens or hundreds of thousands of people that you could possibly email, you'll need a lot. At Aurora, we buy ~20 domains for each client. What you should know for now is that it's better to buy too many domains than too few. Nothing will happen if you buy too many, but buying too few and over-sending on them could get you penalized for spam.

Buying domains is easy and you can do it just about anywhere: GoDaddy, Siteground, Bluehost, and more—there are 100s of places you can buy domains. At Aurora we use Cloudflare, but it doesn’t make much of a difference. Just make sure that wherever you buy your domain lets you get into the admin settings, which you’ll need so you can optimize for deliverability.

Optimizing your domains for deliverability

There’s so much effort put into optimizing inboxes and emails for deliverability—you may have heard terms like ‘warming up’ inboxes, avoiding ‘spam words’, and the like. But it would be a mistake to jump to those things without first optimizing deliverability at a domain level.

What ‘deliverability’ means: in outbound, deliverability means getting your emails to hit your recipient’s primary inbox, where they will actually see your email. We are not talking about whether your email gets “delivered”, a metric you’ll see on many email-sending products, which just means that the email landed somewhere—which could be spam. The following steps are about optimizing so that your outbound hits the part of the inbox that people actually read.

Handling deliverability at the domain level is mostly about boosting your authenticity in the eyes of ESPs, like Gmail. Fortunately, this is fairly easy. Roll up your sleeves and you can get most of this done in an hour or so. At the domain level, you need to set up three main things:

• SPF
• DMARC
• DKIM

These three acronyms, while they look rather scary, are easy to set up and provide some of the basic foundations for work we'll do later. Here is how to set up each.

Side note: You may have also heard of the concept of ‘domain warming’, which refers to increasing your domain’s reputation in the eyes of ESPs. This is not something you really have to do on its own. Warming up your domain is mostly a downstream effect of 1. The authentication steps in this section, 2. The inbox warming in the next section, and 3. The actual performance (and non-spamminess) of your emails and campaigns, which we’ll cover later on.

Creating email inboxes and optimizing them for deliverability

Inbox-level deliverability optimization is the highest-leverage deliverability work there is.

Sure, ESPs like Google care about your domain and the contents of your email. But what they care about most is the individual sender—are you a trustworthy person?

As you might expect, this is also the trickiest part of deliverability optimization. But even though some of the next steps are tricky, they should take you no more than ~10 hours to implement, even if you have lots of email inboxes. It begins, of course, with actually setting up your email inboxes.

Setting up your email inboxes

At Aurora, we set up 3 inboxes per domain. You could set up more—it’s the temptation, because setting up lots of domains takes work—but we don’t do this at Aurora. That’s because the more you send from each domain, the more spam reports there are per domain. More spam reports on a domain increases the chance that the entire domain crosses a spam threshold and gets a bad reputation for being spammy. To reduce risk, diversify sending across more domains.

You have 3 main options for setting up inboxes:

• Google: This involves setting up Gmail accounts with Google Workspace.

• Microsoft: This involves setting up Outlook accounts with Microsoft 365.

• Private IP: This involves setting up your own private email server infrastructure.

There are other options. But these are the main 3. And if you want to avoid headaches, I’d recommend 1. Google and 2. Microsoft. You can mix and match if you want, with some domains on Google and some on Microsoft. But what I’d especially recommend against is using a private IP.

Why no private IP? Whether you do this in-house (extremely complex) or use a service like Maildoso (less complex), veering away from traditional ESPs is playing a losing game. As for why, imagine two outbound campaigns: one is a batch of 100 emails from trusted Gmail and Outlook accounts, and the other is a batch of 100 emails being sent from a little-known ESP network. Which one do you think is more likely to get sent to spam? It’s also true that lots of the people who use private IPs are scammers—they’ve been blocked by companies like Google—which earns private IPs a deservedly bad reputation. As a result, sending mass cold outbound on a little-known ESP network tends to be a straight shot to the spam folder.

Helpful tip: If you set up with Google, which I recommend, you’ll be setting up the emails via a Google Workspace account. You can set up multiple domains on a Google Workspace account, which means there may be a temptation to set up all of your domains and inboxes on the same workspace account. Don’t do this. A good rule of thumb is 3 inboxes per domain, and 2 domains (so 5 or 6 inboxes) per Google Workspace account. The reason why is that, if some of your inboxes or domains on a Google Workspace account get flagged as spam, you could lose the whole account.

The practical step-by-step of setting up the inboxes is straightforward—we won't get into a step-by-step tutorial of that here, as there are plenty of good ones online (like Google's own site). Or you could ask AI. What's important to mention here, however, is that you be careful about which IP addresses and browsers you are managing accounts from.

ESPs, like Google, don’t want one person to be managing hundreds of email accounts. And if you simply open your browser and spend a few hours setting up hundreds of inboxes on many dozens of domains, ESPs will flag that and start to making things harder for you: they might ask you for a phone number, then limit how many times you can use that phone number. They may ask you to verify your identity with a text message. Or they may simply not let you continue to create inboxes and add accounts.

How do you get around this so you can set up as many accounts as you want? Two ways:

1. VPNs. When you set up email accounts, use a VPN and change it regularly. Use high quality American IPs. This makes it harder for ESPs to know that it’s just one individual setting up the accounts.

2. Antidetect browsers. There are browsers, like Adspower and Wavebox, that take extra steps to conceal your fingerprint (digital identity) from websites. This makes it harder for Google to start placing limits on how many accounts you can manage from your browser.

Use these. Then set up your inboxes with the names of real humans that work on your team. At Aurora, we found it’s usually most effective to use the names of the founders or other people that can open doors at the company (e.g. your Head of [Department] type roles). Prospects often respond better to this than getting an email from a low-level salesperson. It’s fine if the low-level salesperson is managing outbound on behalf of the founder, but I find it’s effective to use the name of people who are higher up. This isn’t one-size-fits-all advice, though—think about what makes sense for your company. And, yes, use profile pictures!

Once your inboxes are set up, you’re ready to start warming.

Warming your email inboxes

Once your inboxes are ready you could, in theory, start sending outbound at scale. But you shouldn’t. Instead, you should warm your inboxes first—this helps ESPs recognize each individual account as a trustworthy sender.

You can think of the way an ESP (like Google) views your inbox as the way you might view a friend you made last weekend compared with a lifelong best friend. When you just meet someone, your guard is up. It takes time for them to gain your confidence and trust. Any red flags you see early on in a new friend are just cause to stop spending time with them entirely, whereas if your lifelong friend makes a mistake you’re more inclined to give them another chance.

Right now, your inbox and ESPs like Google and Microsoft are new friends.

If you started sending 100s of cold outbound emails from the jump, you’d be sending out clear red flags that you aren’t a human, you’re actually a bot spamming messages. And you’d get sent to spam. Three main reasons for this:

1. You’re sending too much volume (humans don’t send 100s of emails a day).

2. You’re sending the same templated message to a bunch of people.

3. The engagement rate (replies, opens, etc.) on your email is lower than average.

Your activity ends up looking like this as a result:

So before you send a single piece of cold outbound, you’ll want to make your domains look like real, normal people. You want to make lifelong friends with the big ESPs. Here’s how.

The right way to warm your inboxes

If you’ve ever researched email warming, you’ve likely seen 100s of different “warming tools” out there that claim you just give them access to their email and they warm your account.

These tools generally work by managing lots (100,000s) of email accounts, sending emails from your inboxes to those accounts, and manufacturing engagement that replicates what a normal human email account might look like.

You could do that on your own, but as you might be able to guess, warming is exceedingly difficult to do on your own. Most warming tools—including our warming feature at Za-zu—have invested tens or hundreds of thousands of dollars into the infrastructure they use. If you want to start sending cold outbound reliably and quickly, you’ll want to use a warming tool.

My strongest piece of advice as you choose a tool is to warm from the same IP you are going to send outbound from. This makes most warming tools a problem, because if you use a standalone warming tool and then use a separate email sequencer, you'll be warming your inboxes from a different IP address than you’ll be sending outbound from.

ESPs aren’t stupid, and if they guess what you’re doing, your cold outbound campaigns are likely to suffer. Za-zu fixes this for you—our product is an email sequencer with built-in warming, so you can warm from the same IP you send from. Learn more here.

Not all warming tools have the same kind of functionality, either. A few things you should look for as you think about how you’re going to warm emails:

• Warming pool quality: Many cheap warming pools (and tools that use them) have spam traps in them, placed by ESPs. These are inboxes that only exist in the warming pool—meaning that if you email them, ESPs know what you’re doing and will send you to spam as a result. The quality of the recipients in the warming pool matters, too. Getting replies from trusted inboxes is extra helpful in the same way that a recommendation from a good friend is better than one from a stranger.

• Warming email frequency: At Za-zu, we slowly ramp up a new inbox, slow down when cold outbound starts, then try to keep engagement rates steady. This is what a good warming tool should do, but not all of the options out there actually do this.

• Warming email copy: A lot of warming tools will send generic emails, like “Office party at 6pm?”, which is fine on its face but a problem if the cold outbound you’re sending is selling a payroll solution to startups. The emails you use for warming should have similar copy and topics to the emails you’ll use in your cold outbound campaigns. ESPs should not be able to tell the difference between your warming emails and your cold emails.

• Randomization: Part of good inbox warming means randomizing engagement—you don’t want the exact same response from every email you send to, and you don’t want your reply rate to stay the exact same forever. Real-life is more complicated than that, so good warming involves randomizing within some boundaries to replicate what a normal account would do.

Find a tool that can do all of these things for you. At Za-zu, for example, we use AI to make sure there are no spam traps in the warming pools (and offer a private pool for larger customers). We also write warming emails based off of copy in current and drafted campaigns—so ESPs don’t raise eyebrows when you start sending.

Side note: The rest of this warming section will range from “interesting” to “extremely useful” based on how you’re warming your emails. If you’re using a tool like Za-zu that effectively does everything for you, the following is good to know but not directly actionable—we’ll handle it. If you’re using a warming tool that requires more manual work (or you’re attempting to do this yourself) then the following includes information directly applicable to what you’re working on right now.

If you aren’t interested in learning more of the workings of email warming, skip to the next section where we cover evidence-backed methods for writing a great cold email.

Email warming best practices—before you start sending outbound

The most intensive part of warming comes before you’ve sent anything. You want to go from “here’s this person who just opened an account” to “this is a trusted sender who sends good emails to other trusted senders”. Each ESP has their own profile on you, so it’s in this initial warming phase that you’ll want to build a good reputation with at least the Google and Microsoft.

One common approach is to start warming an inbox by sending the maximum daily volume you’d want to see from a normal email (20 emails). At Za-zu, we instead start by slowly ramping the inbox up to that 20-email volume over the course of a couple of weeks. When employees start at a new company—the primary reason for a new Google Workspace account—they’re typically onboarding, learning the ropes, getting to know people. They are likely to send less emails on Day 1 than Day 3, and less emails on Day 3 than Day 7. We replicate that.

After you’ve been warming for at least 3 to 4 weeks, you’re ready to start sending.

Email warming best practices—after you’ve started sending outbound

One failure mode in cold email is to turn off your warming as soon as you start sending cold outbound: this is what happens a lot when people use external tools, decide they’ve “finished warming”, and start sending their campaigns.

But a loaf fresh out of the oven doesn’t stay warm forever, and neither do your emails. You don’t want to completely turn off your warming work once you’ve started sending cold outbound, but you do want to be flexible about it: your goal is to maintain high-quality engagement statistics without harming your ability to send the volume of outbound you want to send.

If your cold outbound campaign goes well and gets lots of replies, you may not need to do much warming—maybe just a few emails per day, or per week. But if your cold outbound campaign tanks and your engagement rates along with it, you’ll want to dial back on the outbound and dial up on the warming to make sure you don’t send any red flags to ESPs. Generally you also want to have warmed inboxes that you’re not using for cold outbound, so that if one inbox tanks you can quickly swap it for a warmed one without sacrificing on volume.

This is all hard, technical, thorough work, and managing it at scale would be nearly impossible manually without a team of people dedicated to the task. That’s why we decided to automate it when building Za-zu, so you can focus on what matters—writing emails and making sales.

Speaking of writing emails…

III. Writing Great Emails

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.

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.

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:

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.

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.

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.

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.

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.

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.

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:

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 pho-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:

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.

Helpful tip: One thing I’ve noticed is that most people, by default, write cold emails more formally than they need to. It’s only natural—you aren’t actually writing an email to someone you know, and something in your mind pushes you to be more formal than you need to. Push back against that urge by adjusting your first drafts a notch or two more casual than you initially thought.

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.

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.

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.

Examples of cold emails that have worked well

Email context: A marketplace for selling businesses online was looking to get more dealflow for their buyers. This campaign focused on emailing companies in specific industries and revenue numbers, letting them know that the emailer had buyers available, and asking if they’d like to have a quick chat about getting introductions to buyers.

Email context: A company that helps companies with capital and finance (like profit sharing) was running a campaign to startups to help them share profits more smoothly.

Email context: A company that helps companies find offshore talent was reaching out to companies with job postings in Latin America.

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.

IV. Sending Personalized Outbound at Scale

Intro

It used to be that if you wanted to send someone a valuable email that was personalized just for them, you had to write that email manually. Most sales reps today are still doing this: find a prospect, research them, spend a real chunk of time writing a personalized email for them. This was the greatest bottleneck to automating effective cold outbound.

Recent developments in AI, however, make it finally possible to do prospect research and email personalization, at any scale. That’s what this chapter is all about. You’ve learned how to prepare to send outbound, you’ve learned how to warm your domains and your inboxes, and you’ve learned how to craft a winning email—now it’s time to automate it all and start sending.

What we’ll cover in this chapter

1. How to use AI to personalize cold emails.
2. How to structure your cold outbound campaigns.
3. Best practices for sending at scale (without hitting spam).

It’s at this stage you will want to consider how you will want to send your emails, personalize them with AI, and monitor your campaigns. The rest of this chapter will assume that you have a way to do so. There are a number of email sequencers out there today that you can use, most of which will require varying degrees of tinkering to get them to work in a useful way.

Or you could try the product I have been building over the last year: Za-zu. It’s the email sequencer built for personalized outbound at scale, and it can do everything from warming your accounts to implementing all of the smart AI tactics we’ll discuss below. See the product here.

Enough self-promotion—let’s talk tactics.

How to write cold emails that AI can personalize

If you read the previous chapter on writing emails, you know the ingredients for an effective cold email. If you’ve practiced, you can probably write a good cold email right now. And so arises the question that’s been the bottleneck to good outbound at scale:

How do I automate emails at the quality I could write manually?

The key isn’t to have AI write emails on its own—the AI tools we have today are terrible at that. Instead, hand AI great emails and have it fill in the personalizable blanks. The way we write at my agency, Aurora, is like this:

1. Write a dream email to one person. Forget about AI. Imagine it’s 1:1.
2. Train AI to send that dream email at scale by filling in the personalized pieces of info.

This may sound a touch confusing or vague, so let’s walk through the steps.

Step 1: Writing a dream email

Imagine that I’m running a campaign to sell Za-zu to companies who raised in the past 6 months and have open sales jobs posted on their site. You run a seed-stage AI customer support startup called Hypothetical Company that fits the criteria.

Here’s a completely hypothetical 1:1 email I could write to you.

"Hey, Reader —

Congrats on the recent raise (Lachy Groom also funded a previous company of mine, was generally helpful).

Happy to see that Hypothetical Company looks a bit different from all the generic/gimmicky AI support startups out there.

Looked at your job board and noticed you're hiring for sales. Imagine you're planning to use outbound to gain significant early/high ROI traction?

If so - you should check out Za-zu, my company. It's an email sequencer that lets one smart growth person send personalized outbound at the scale of 50 SDRs.

I'd love to show you the product. Would it be crazy to chat this week?

Matt"

This is the kind of email that previously would have been impossible to automate at scale. Now it’s possible, and here’s how you might go about doing it.

Step 2: Converting the dream email to an AI-usable template

Now I want to take that email and replicate it at scale with AI. Here’s how I’d go about doing it.

Hey, {{first_name}} —

Congrats on the recent raise {% if {{investor_name}} %} ({{investor_name}} also funded a previous company of mine, was generally helpful. endif %}.

Happy to see that {{company_name}} looks a bit different from all the generic/gimmicky {{startup_category}} startups out there.

Looked at your job board and noticed you're hiring for sales. Imagine you're planning to use outbound to gain significant early/high ROI traction?

If so - you should check out Za-zu, my company. It's an email sequencer that lets one smart growth person send personalized outbound at the scale of 50 SDRs.

I'd love to show you the product. Would it be crazy to chat this week?

Matt

There are various levels of complexity at work in this email—let’s look at each.

- Campaign level: The email is personalized by default based on how we've chosen who to email (companies that have recently raised and have open sales jobs). That means some of the template is still personalized, even though AI isn't touching it.

- Copy and paste: The {{first_name}} variable in this email is the simplest one—you just need the AI to paste the name of the prospect.

- Summarization and normalization: The {{company_name}} {{startup_category}} variables go beyond the simple copy and paste. The company name, for example, needs to be normalized—if a company's name is Hypothetical Company Industries, Inc., pasting that entire thing in an email will feel inhuman. So the AI shortens it to 'Hypothetical Company'. And {{startup_category}} needs to be a human-sounding summary of the specific niche or industry that the prospect's company is in.

- If-then: The investor line at the beginning of the email feels tricky, but it isn't. You just need to ask AI to cross-reference the list of the prospect's investors with your own lists of previous investors (relevant in this case, since I have them). If there's an investor in common, the line will be included—if not, it will be cut.

AI personalization can, of course, go as far as you want it to. It can write entire sentences or paragraphs based on the instructions you give it. At Aurora, for example, one campaign for a podcasting agency that found success included a bullet-point section where AI offered personalized podcast ideas for the prospects. Always write your dream email first, then figure out how to replicate that email with AI at scale second.

You can get carried away here, of course. The more complexity you give AI, and the more words it has to write, the higher the probability that you will plant a red flag—that the email will have a non-human smell to it. Be careful about how you use AI and test it before launching a campaign.

How to prompt AI for quality personalization

It’s reasonable enough, with some practice, to write good cold emails and identify the personalized variables within them. But the next step is just as important: getting AI to generate good personalized variables at scale.

Because while AI personalization sounds good in theory, it can go very wrong very fast—and can plant a number of red flags that make the email feel spammy and worthless to recipients. For example, a section like the following is simple in theory:

Easy, right? Now just imagine this very possible output for this variables:

We’ve jumped straight from a good personalized email to something that was clearly not written by a human, and the chance that somebody is going to respond to an email this opener is little to none. So how do we fix it?

At Aurora, I built an internal playbook for AI prompting based on the variables we use—and I suggest you do the same. Your playbook will look different from ours, but you can find ours here if you’d like to see how we think about it. Broadly though, think about AI prompting much like you’d think about giving instructions to a real human for a job like this.

• Instructions: The specific directions for the prompt, similar to how you’d write a brief for a task for somebody at work.
• Persona: The personality and expertise AI should take on as it does research and carries out the task—sometimes this can lead to better output.
• Examples: Clear examples for the AI to learn how it should provide its output.

Here’s a look at how we go about each.

Writing instructions

The AI prompt instructions format we have found most effective is as follows:

1. Start with the input. Usually this is something that’s being pulled from a data enrichment tool (like Clay) or otherwise from somewhere on the internet, and it is the piece of data that the AI will be manipulating. For example, if you were going to have AI come up with cold outbound campaign ideas for a company, the input might be general information about the company—like their LinkedIn description.

2. Write your instructions as clearly and concisely as possible. After giving AI the input, write instructions for what to do with that input. Most of our instructions, even the complex ones, aren’t more than a few paragraphs long.

3. Include helpful guidelines. Many of our prompts include Do’s and Don’ts that help the AI get the personalization right and avoid mistakes. You’ll likely want to do some testing to identify common mistakes the AI makes, then update your Do’s and Don’ts accordingly.

You don’t have to do these things in this order, but having all of these elements in your instructions generally leads to the right outcomes. Here are example instructions for generating podcast ideas.

Crafting the AI persona

It’s sometimes helpful to create an AI persona to do one of two things:

- Get better output: It may sound strange, but often if you tell AI that it is an expert at something, the results it produces about that thing will be better. This isn’t always necessary, but it can help from time to time. I recommend lots of testing.

- Use the right tone: If AI is writing things that tone has an impact on, like personalized introductions or ideas for things, giving it a persona can help it land on the right tone. Again, you’ll want to do lots of testing and compare outcomes.

The best heuristic for drafting a persona is to think of how you’d describe someone who would be really good at what you are asking AI to do. For example, if you were going to prompt AI to accurately summarize the niche a company is in, you could write a persona like this:

This is a persona we have used in 100,000s of emails at Aurora. It works. Write something like this for everything you’d like AI to generate and see how it impacts the results. A persona will not always be necessary nor will it always be helpful, but for certain tasks (especially more complex and nuanced ones) it can occasionally help.

Choosing the right examples

LLMs like ChatGPT are extremely good word predictors. At a basic level, they look at what has been written so far and guess as to which word comes next. This is why giving LLMs positive examples of the output you are looking for is so high-leverage—you’re creating a new, small, powerful dataset for the AI to model its answers on.

Examples tend to work best when you give the AI both an input and an output. Show AI an example of the input they’ll receive, then show it an example of what a positive output would look like. Here’s an example for coming up with the niche of a business:

If you can give more than one good example, do so—it would be difficult to give too many examples. Feel free to test as you’d like, but in my experience you will see diminishing returns as you add additional examples. The difference between 0 and 1 example, or 1 and 3 examples, can be serious. But the difference between 50 and 52 examples is not likely to be noticeable.

How to craft effective outbound campaigns at scale

Now arrives the grand finale of everything you have read up to this point: it’s time to create campaigns in your email sequencer, start sending them, and hopefully, to start making money.

You have most of the puzzle pieces by now. You know:

• The principles behind why outbound works.
• How to prep your infrastructure for deliverability.
• How to craft a great cold email.
• How to use AI to personalize your great emails at scale.

There’s still some art and science to getting this right—sending campaigns with the wrong scope can minimize your results, and testing your campaigns improperly or insufficiently can mean you miss out on insights to write better emails.

Structuring a great outbound campaign

One of the many downsides of manual, 1:1 email-sending is that you can’t get very clever with the way you structure campaigns. You may have an internal playbook that tells you how long to wait until you follow up, but you usually won’t be rigorously testing different kinds of wording and messaging across ~5 to 10 email variants for each stage of your campaign.

When you send with a good sequencer at scale, you can. At Aurora, our campaign structures typically look something like this.

A quick explainer of this structure:

- Campaign: The idea for the series of emails. Usually this is either a specific audience or a combination of both a specific audience and product offering—a modified version of the example above might be, “Cap table management product for pre-Series C startups hiring for sales.”

- Stages: Each stage represents one individual email to a prospect. It generally helps to come up with a broad goal, or idea, for each stage.

- Email variants: You’ll write different email variants to test different messaging, tone, and email structure within each stage of your campaign.

Every campaign is different, so the number of stages and email variants you want depends on your goal. Typically though, we aim for campaigns to have between 4 and 6 stages, and for between 3 and 6 different email variants per campaign.

If you’re new to this, it may feel slightly overwhelming (or at least different) from how manual outbound works. Once you’ve written a few campaigns, though, you’ll find that this campaign structure is magical—for example, when Variant C in Stage 3 does particularly well and you realize you’ve found a surprisingly great angle for new campaigns.

Your email sequencer should give you in-depth data about each stage and email, so as you send and get results you can start optimizing for even more replies. More on that in a bit.

What about timing?

It’s up to you to decide how many days should pass between each email, but we often do something like this:

• Between Stage 1 and 2: 2 days
• Between Stage 2 and 3: 4 days
• Between Stage 3 and 4: 7 days

The logic here is simple: if someone doesn’t reply to a couple of emails within the matter of a couple of days, they likely aren’t interested right now, were too busy to reply, or didn’t see the email. In any case, there isn’t much benefit to flooding their inbox—let it rest a week or so, then follow up. If after your third (or fourth, or fifth) email you still haven’t heard back, let it rest even longer and try once more. Often, by the final stage, you’re just letting the prospect know you won’t be emailing them any more in the future.

So, about stages: what are you actually supposed to write?

Deciding what messages to convey in each email stage

While manual outbound can often be random, building large-scale campaigns in your email sequencer allows you to be extremely thoughtful about your campaign. As a general rule, each stage in your campaign should have a high-level theme that the emails within the stage follow. For example, here is a hypothetical way to structure themes by stage:

• Stage 1: Intro and introduce primary value prop
• Stage 2: Reinforce primary value prop and introduce secondary
• Stage 3: Recap primary and secondary value props
• Stage 4: Break up, ask if someone better to email and say this is your last email

You can get wonderfully creative with every stage, but at a minimum it’s good to have a narrative arc for your campaign. Not only does this lead to more effective campaigns, but if one stage significantly outperforms another one—say your Stage 2 outperforms Stage 1—then you have new insights about what kind of messaging actually resonated with your audience.

Surprising fact: Some of our clients at Aurora have thought they had their messaging figured out—they’d paid the branding agencies, done the storytelling sessions, etc.—but the value props that resonated in actual outbound campaigns ended up surprising them. The right messaging will change by campaign, audience, and stage. Avoid being overconfident and instead, try a wide range of plausibly effective messaging to see what really works. You may be surprised.

Once you’ve decided on the broad strokes of narrative for your campaign and stages, you can start writing the emails. I’ve found that, before writing emails, it helps to outline this entire process—don’t let it live in your head. Write down the audience, write down the goals of the stages, and write down the high-level points that will live in each email. For example…

- Stage 1: Intro and introduce primary value prop
- Variant A: Company mission-based intro + aggressive CTA (short)
- Variant B: Headcount-based intro + soft CTA (short)
- Variant C: Company mission-based intro + aggressive CTA (long)
- Variant D: Headcount-based intro + soft CTA (long)
- Variant E: Super short email with a simple question - nothing more.

You don’t have to outline exactly like this, but it can be helpful to have a general idea of the focus of each email before you write it. These outlines can also help you be more rigorous about what you’re testing. Once you’ve defined the unique traits about each email, it’s easy to look at the email performance data and identify the specific variables that are making your emails succeed.

Writing the emails themselves

Most of the email-writing process should be pretty simple—use what you learned in the section of the playbook about writing emails, or go reference it again if you want some help.

There is a unique twist when you’re sending with AI at scale:

Not every email should read exactly the same.

ESPs, like Google, don’t like seeing the exact same email being sent to 100s or 1000s of individual people. There are very few real-life situations where that happens—so if it’s the main kind of activity coming from your domain, you’ll raise red flags.

This is where you’ll want to do something called spintaxing: randomly changing words in every email so they aren’t identical. Spintaxing works by finding synonyms to specific words or phrases in your email, then providing a few options for your email sequencer to randomly choose when it sends the email. For example, a spintaxed version of an intro line might look like this:

Simple enough, and any email sequencer built for outbound at scale (like Za-zu) will either automatically do this or at least make it possible to spintax with some tinkering.

The one failure mode to watch out for when spintaxing is choosing alternative words that make the email worse—something that I’ve seen happen on occasion.

Just because a word is a synonym doesn’t mean it’s an equally valuable replacement in the email, so evaluate every spintaxed variable as rigorously as you would if you were evaluating your draft of a cold email. Only include spintaxed variables that are just as good as the original.

Optimizing based on data

Your email sequencer, if it is good, should give you in-depth data on the performance of your campaigns. At the minimum you should have metrics like open rate and reply rate across both stages and individual emails. And hopefully your sequencer gives you data on what kinds of replies you’re getting—a good sequencer should be able to automatically classify replies into Positive and Negative categories, with more specific subcategories falling under each of those.

Most of what to do with this data is obvious—take learnings and implement them for future campaigns. If you outlined your campaign in the way I suggested earlier in this section, you’ll have an easier time identifying why certain emails and stages do better than others.

If it quickly becomes obvious, and by this I mean statistically significant, that one email (or series of emails) in your campaign is outperforming all the others, there are a couple of things you can do:

1. Reroute all sending in the campaign to just the highest-performing series of emails.
2. Pause new sending for the campaign and write a new one with more variations in the direction of the messaging that worked best in your first campaign.

This is a tactic commonly used by copywriters (including by Rajiv and the team at Product Hunt when giving advice on taglines). Write dozens of different angles, focus on the ones that work, then write more variants in the same direction of your best angles. It’s good advice for copywriting and equally good advice for sending effective outbound.

Before long you should be sending effective, powerful, ultra-optimized campaigns. And booking as many meetings as your sales team can handle.

V. Launching Your campaigns

There is only so much reading you can do about something like outbound until it’s time to get out there, get your hands dirty, and launch your dream campaigns. Now is the time. I hope you’ve found the information in this handbook useful. Write to me on the Za-zu community forum if you have feedback, thoughts, or questions. I’d love to help to the extent that I can.

From here, the path is clear: set up the infrastructure. Write your emails. Find somewhere to send your emails from, like Za-zu—the sequencer I’ve built for outbound at scale, dedicated to people like you. Then, of course, there is only one thing left to do: start sending.